The 100 Best Movies of the 2000s

Its lights, camera, action as we look back at a decade's worth of super fresh flicks! However, the infamous Scooby-Doo movie didn’t make the list… weird.

'The 40 Year Old Virgin'
Universal Pictures

Image via Universal Pictures

'The 40 Year Old Virgin'

This feature was originally published on September 21, 2009

The first decade of the new millennium (a.k.a. The Aughts) is drawing to a close, but we're not done with it yet. Complex has been looking back at the decade with our Best of the 2000s series, featuring retrospective of everything from albums to sneakers. And now we're proud to present our look back at The 100 Best Movies of the 2000s. Our tastes are pretty eclectic (we call ourselves Complex, after all), so we've got everything from loud comic blockbusters and juvenile cock 'n' balls comedies to subtle indie romances and rock documentaries. Click through the list to see if your favorites cracked our top 100, and maybe you'll rediscover a forgotten flick or two...

100. Tropic Thunder

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Released: 2008

Director: Ben Stiller

Starring: Ben Stiller, Robert Downey Jr., Jack Black, Brandon T. Jackson, Jay Baruchel

A pampered cast of actors thinks they're playing soldiers in a Vietnam movie but unwittingly get dropped in the middle of a real-life drug war. The jokes are fast and furious, but the flick is most memorable for Downey Jr.'s amazing take as a white dude in blackface. Way more convincing than Ted Danson.

YOU AUGHTA KNOW:

Disability groups picketed the film's premiere because of its Simple Jack subplot. Man, that's stupid.

99. Slumdog Millionaire

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Released: 2008

Director: Danny Boyle

Starring: Dev Patel, Freida Pinto, Madhur Mittal, Anil Kapoor, Irrfan Khan

Yeah, the hype got a little extra, but Slumdog is definitely worth however many rupees your Netflix bill converts to. Boyle brings his white-man eye into the slums of Mumbai for the heart-lifting story of an orphan who spends his whole life fighting the odds for love...and one million dollars! Cue triumphant bhangra music!

YOU AUGHTA KNOW:

The big pit of shit that young Jamal leaps into was—thankfully—not made of real human excrement. It's actually a combo of peanut butter and chocolate. No wonder lil' homie looked so excited to be covered in it!

98. Super Troopers

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Released: 2001

Director: Jay Chandrasekhar

Starring: Jay Chandrasekhar, Kevin Heffernan, Steve Lemme, Paul Soter, Erik Stolhanske, Brian Cox

The Broken Lizard comedy troop's tale of Vermont State Police fuckups has laughs on lockup with all kinds of drugs, dickhead cops, trooper pranks, and even an arresting boob shot if you pay close enough attention to the German tourist scene.

YOU AUGHTA KNOW:

The characters from the film are inspired by interactions the Broken Lizard crew had with Vermont State Troopers.

97. Night Watch

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Released: 2004

Director: Timur Bekmambetov

Starring: Konstantin Khabensky, Vladimir Menshov, Maria Poroshina, Galina Tyunina, Mariya Poroshina

In modern day Moscow, the supernatural forces of day and night break a centuries-old truce and feud over the Great One, a child who will pick sides and make one more dominant. This action fantasy is just like your parents' divorce, only fun!

YOU AUGHTA KNOW:

Night Watch became the highest-grossing movie in post-communist Russia (until Turkish Gambit broke its record a year later).

96. Jackass: The Movie

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Released: 2002

Director: Jeff Tremaine

Starring: Johnny Knoxville, Steve-O, Bam Margera, Chris Pontius, Ryan Dunn, Jason "Wee Man" Acuña

By the time this hit theaters, the MTV show was already a modern classic. The movie took it to the next level, showing off tons of stunts not suitable for TV. The boob tube ain't ready for a Ryan Dunn getting an X-ray to see the toy car he shoved up his ass.

YOU AUGHTA KNOW:

Scenes that may have resulted in legal action against the Jackass crew were cut.

95. The Squid and the Whale

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Released: 2005

Director: Noah Baumbach

Starring: Jeff Daniels, Laura Linney, Jesse Eisenberg

Eisenberg shines as a teenager dealing with the divorce of his parents in Park Slope, Brooklyn in the 1980s. Partly based on director Baumbach's life, the film effectively (and often comically) captures how familial strife has repercussions on every member of the clan. Special props to Billy Baldwin for his hilarious portrayal of a libidinous tennis instructor.

YOU AUGHTA KNOW:

Anna Paquin plays Daniels's jump-off in the film, just nine years after playing his daughter in Fly Away Home. From daughter to lover in less than a decade? Word to Soon-Yi!

94. Y Tu Mamá También

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Released: 2001

Director: Alfonso Cuarón

Starring: Gael García Bernal, Diego Luna, Maribel Verdú

Just before landing the gig as the new Harry Potter director, Cuarón warmed up with this serious, steamy film about two teenage guys having sex with an older woman (and each other!) on a road trip. We can totally see why they hired him.

YOU AUGHTA KNOW:

The movie was released without a rating in the U.S. to avoid the dreaded NC-17 stamp.

93. The Devil and Daniel Johnston

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Released: 2005

Director: Jeff Feuerzeig

Starring: Daniel Johnston

This funny and sad documentary biopic chronicles the tortured life of schizophrenic lo-fi songwriting savant and indie rock legend Johnston. Sure, it mines illness for laughs, but unlike other rock docs that feature plane crashes, Devil has a (more or less) happy ending.

YOU AUGHTA KNOW:

TDADJ took four years to complete, but it was worth the effort, winning the Director's Award at the 2005 Sundance Film Festival.

92. Shaolin Soccer

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Released: 2001

Director: Stephen Chow

Starring: Stephen Chow, Zhao, Ng Man Tat

Soccer and Kung Fu. Put them together and the result can either be completely ridiculous or unbelievably awesome. Players using roundhouse kicks to score goals makes us lean towards the latter.

YOU AUGHTA KNOW:

Director Steven Chow dubbed his own voice for the American version of the film.

91. Mulholland Drive

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Released: 2001

Director: David Lynch

Starring: Naomi Watts, Laura Harring, Dan Hedaya, Justin Theroux

A very, very, very strange (what'd you expect from David Lynch?) film noir about Hollywood, car crashes, lesbianism, the true nature of identity, and probably about fifteen other heady things we totally missed waiting for the next girl-on-girl scene.

YOU AUGHTA KNOW:

MD was originally conceived as a television pilot, with the plot left intentionally open-ended for a possible series.

90. Death to Smoochy

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Released: 2002

Director: Danny DeVito

Starring: Robin Williams, Edward Norton, Catherine Keener, Danny DeVito, Jon Stewart, Michael Rispoli, Harvey Fierstein

In this tragically slept-on dark comedy, disgraced kids show host Rainbow Randolph (Williams) plots revenge against his squeaky-clean replacement, a rhino named Smoochy (Norton). Seems childish but it's about as kiddie as St. Ides Special Brew Freeze and Squeeze.

YOU AUGHTA KNOW:

Jim Carrey was attached to star at one point but dropped out to do The Majestic (which also bombed, and actually deserved to).

89. The Descent

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Released: 2005

Director: Neil Marshall

Starring: Shauna Macdonald, Natalie Mendoza, Alex Reid, Saskia Mulder, Nora-Jane Noone

In this slow-building horror sleeper, a group of women squeeze into an unexplored cave system on a bonding trip and find themselves trapped underground with bloodthirsty mole creatures. We're pretty sure it's a metaphor for girl-on-girl STD transmission during menstruation but we could be wrong.

YOU AUGHTA KNOW:

Even though the "crawlers" are seen only briefly, Marshall wanted them to have fully developed personalities, so he used professional actors to portray them instead of stuntmen or dancers.

88. Bad Santa

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Released: 2003

Director: Terry Zwigoff

Starring: Billy Bob Thornton, Bernie Mac, Tony Cox, Lauren Graham, John Ritter

We always knew those mall Santas were up to no good, and Billy Bob Thornton nailed it as a shady Santa who gets drunk on the job, swears up a storm, and smashes chicks on break. Are they hiring for the holiday season yet?

YOU AUGHTA KNOW:

The movie is dedicated to John Ritter. This was his last live-action role. He died two months before the movie hit theaters.

87. Talk to Me

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Released: 2007

Director: Kasi Lemmon

Starring: Don Cheadle, Chiwetel Ejiofor, Mike Epps, Martin Sheen, Cedric the Entertainer

After getting out of the bing, prison DJ Ralph "Petey" Greene (Cheadle) becomes a popular Washington D.C. radio talk show host and community activist in the 1960s and '70s. You see, the fear of having a train run on you isn't all prison's good for.

YOU AUGHTA KNOW:

The real Greene started DJing while serving a 10-year sentence for armed robbery.

86. Girlfight

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Released: 2000

Director: Karyn Kusama

Starring: Michelle Rodriguez, Jaime Tirelli, Paul Calderon

A troubled, violent 18-year-old girl (Rodriguez) with an abusive father discovers boxing and channels her rage in the ring. We don't usually go for chicks who could black our eyes, but Rodriguez's performance is a knockout, even if her character's kinda mannish.

YOU AUGHTA KNOW:

Rodriguez beat out over 300 other women for the part in her first audition ever.

85. Observe and Report

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Released: 2009

Director: Jody Hill

Starring: Seth Rogen, Ray Liotta, Michael Peña, Anna Faris

After playing several harmless, well-intentioned slackers, Rogen goes to the comedic dark side as a bipolar and impotent mall cop (he's no Paul Blart) trying to catch a flasher so he can bang one of the perv's victims (Faris). You know you're watching something special when it makes date rape funny.

YOU AUGHTA KNOW:

Ray Liotta's police detective role was written for Danny McBride, who had scheduling conflicts and instead made a cameo as "Caucasian Crackhead."

84. Riding Giants

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Released: 2004

Director: Stacy Peralta

Starring: Laird Hamilton, Greg Noll, Jeff Clark, Dave Kalama

Wave porn disguised as a surfing documentary about the rise of big wave surfing, particularly Laird Hamilton's tow-in crew on Hawaii's North Shore. It's like surfing on steroids. Congress should really look into it.

YOU AUGHTA KNOW:

Hamilton's crew regularly surf 35-foot waves, and have even ridden 70-foot swells.

83. Drumline

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Released: 2002

Director: Charles Stone III

Starring: Nick Cannon, Zoe Saldana, Orlando Jones

A funky drummer from New York (Cannon) joins the drumline at fictional Atlanta A&T University and clashes with his jealous, traditionalist band leader. This is really the only movie in which we've felt the Cannon blast. D-d-d-d-d-d-d-d-drum roll pause.

YOU AUGHTA KNOW:

The movie was inspired by the life of Dallas Austin, the Atlanta-based producer and songwriter responsible for many of TLC's hits, including "Ain't 2 Proud 2 Beg" and "Creep."

82. Sexy Beast

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Released: 2000

Director: Jonathan Glazer

Starring: Ben Kingsley, Ray Winstone

You know those houseguests who you used to commit crimes with, but then they come to visit you and hang around a lot longer than they need to? And they piss on the rug and insult your wife and generally torture you for not wanting to join them in one last heist? Man, that sucks.

YOU AUGHTA KNOW:

Kingsley based his performance on his grandmother, who he called "a vile and extremely unpleasant woman."

81. Wedding Crashers

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Released: 2005

Director: David Dobkin

Starring: Owen Wilson, Vince Vaughn, Bradley Cooper, Rachel McAdams

We thought weddings were a time to mourn the death of a man's sex life until we watched Wilson and Vaughn as horny bachelors preying on lonely women. Money, power, and respect work wonders but female jealousy and desperation will get you laid all the same.

YOU AUGHTA KNOW:

Senator and 2008 Republican Presidential Nominee John McCain has a brief cameo in the film. Obama, on the other hand, was focused on winning the presidency.

80. Dogtown and Z-Boys

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Released: 2001

Director: Stacy Peralta

Starring: Sean Penn (narrator), Jay Adams, Tony Alva, Stacy Peralta

A loving documentary (with a killer soundtrack) about the legendary, trailblazing Zephyr skate team of the 1970s. Heath Ledger starred in a thoroughly shitty Hollywood adaptation in 2005, proving that skating rivals only hip-hop in the annals of "Things the Mainstream Fucks Up."

YOU AUGHTA KNOW:

In a Hawaiian jail on drug charges when Z-Boys premiered, Jay Adams was released in 2002, only to land in prison again in 2005 (he was paroled in 2008).

79. Saw

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Released: 2004

Director: James Wan

Starring: Cary Elwes, Danny Glover, Leigh Whannell, Ken Leung, Michael Emerson, Tobin Bell

Victims of the serial killer "Jigsaw" must solve his elaborate puzzles and learn the true value of life or die painfully in his diabolical death machines. Unfortunately for them, this test has no multiple-choice section!

YOU AUGHTA KNOW:

Saw was originally intended for a straight-to-DVD release. The same should be true of its far inferior sequels.

78. Team America: World Police

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Released: 2004

Director: Trey Parker, Matt Stone

Starring: Trey Parker, Matt Stone

Those sick South Park guys spoof Jerry Bruckheimer action movies with puppets in this story of an elite counter-terrorism organization. Seriously, anyone who can't get a laugh out of "durka durka carbomb" or two marionettes engaging in some graphic scatologic sex needs to chill out.

YOU AUGHTA KNOW:

Parker and Stone originally wanted to do an all-puppet version of Armageddon but ran into legal troubles with the movie studios.

77. Ghost World

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Released: 2001
Director: Terry Zwigoff
Starring: Thora Birch, Scarlett Johansson, Steve Buscemi

Two hopelessly ironic, angst-ridden teenagers listlessly look for a life in post-high school suburbia. Based on Daniel Clowes's awesome graphic novel, this movie marked the first time we were legally allowed to notice how hot Scar-Jo is.

YOU AUGHTA KNOW:
Terry Zwigoff's 2006 movie Art School Confidential is loosely based on another Clowes comic.

76. The Ring

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Released: 2002
Director: Gore Verbinski
Starring: Naomi Watts, Martin Henderson

Japanese people are sick, but somehow Hollywood's remake of the old watch-this-video-and-die story managed to be far creepier than the Japanese original. One final scene in particular still gives us the heebie jeebies, which is why we always watch it curled up with ya moms.

YOU AUGHTA KNOW:
Naomi Watts was offered the lead role only after Jennifer Connelly, Gwyneth Paltrow, and Kate Beckinsale turned it down. Wah-wahhhhhh.

75. Mean Girls

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Released: 2004

Director: Mark Waters

Starring: Lindsay Lohan, Tina Fey, Rachel McAdams, Lizzy Caplan, Lacey Chabert, Amanda Seyfried

If you ever wonder "How the hell did Lindsay Lohan get so famous?" then you clearly haven't seen the superb high school comedy that made her a star. Tina Fey blessed "Big Red" with a surprisingly smart screenplay that foreshadowed her 30 Rock style (but none of LiLo's fuckery).

YOU AUGHTA KNOW:

The movie was based on a non-fiction book about the social behavior of teen girls called Queen Bees and Wannabes.

74. The Royal Tenenbaums

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Released: 2001
Director: Wes Anderson
Starring: Gene Hackman, Owen Wilson, Ben Stiller, Anjelica Huston, Luke Wilson, Bill Murray, Gwyneth Paltrow

A bizarre look at a broken family that's funny, sad, and sentimental all at once. After blowing up big with Rushmore, the director's obsessive-compulsive tendency to over-stylize every visual detail really exploded on this one. It's all anal, and that's never wrong!

YOU AUGHTA KNOW:
Despite being set in the modern day, every piece of clothing worn in the film is from the 1970s.

73. Shaun of the Dead

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Released: 2004

Director: Edgar Wright

Starring: Simon Pegg, Nick Frost, Kate Ashfield

A salesman (Pegg) who's only slightly less aimless than his slacker best friend (Frost) tries to win back his dissatisfied ex-girlfriend and deal with family issues during a zombie apocalypse. A romantic comedy with zombies? That's date night done right.

YOU AUGHTA KNOW:

Nick Frost allegedly kept his genitals shaved throughout filming, so he'd have the genuine need to scratch himself, like his character Ed has.

72. Hustle And Flow

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Released: 2005

Director: Craig Brewer

Starring: Terrence Howard, Anthony Anderson, Taraji P. Henderson, Taryn Manning, D.J. Qualls

When he's not pimping hoes and selling drugs in Memphis, small-time hustler DJay (Howard) tries to get his life together by making music. The problem is, pimpin' ain't easy, but it's a helluva lot easier than getting fools to listen to an actual demo tape in 2005. They don't got CD burners in Memphis, playa?

YOU AUGHTA KNOW:

Three 6 Mafia won an Oscar for Best Original Song for "It's Hard Out Here For A Pimp."

71. 2 Days in Paris

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Released: 2007

Director: Julie Delpy

Starring: Julie Delpy, Adam Goldberg

A French photographer (Delpy) and her neurotic boyfriend (Goldberg) meet all her old jumpoffs while hashing out their relationship problems in Paris. Sounds soft, we know, but it's gold for girls. Plus you can throw on the Hilton sex tape One Night in Paris and claim you thought it was a prequel.

YOU AUGHTA KNOW:

Delpy not only directed and starred in the movie but also wrote, produced, and edited it. She even composed the soundtrack!

70. Quills

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Released: 2000

Director: Philip Kaufman

Starring: Geoffrey Rush, Kate Winslet, Joaquin Phoenix, Michael Caine

From his cell in an asylum, the Marquis de Sade (Rush) writes and smuggles out pornographic and politically incorrect literature, irking the sadistic doctor (Caine) Napoleon has sent to "fix" this public menace. If loving porn is crazy, get us a padded cell.

YOU AUGHTA KNOW:

Joaquin Phoenix plays the Abbé de Coulmier, who in real life was a four-foot-tall hunchback. Verne Troyer was busy?

69. Donnie Darko

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Released: 2001

Director: Richard Kelly

Starring: Jake Gyllenhaal, Maggie Gyllenhaal, Patrick Swayze, Drew Barrymore, Jena Malone

After narrowly avoiding death via fallen jet engine, a troubled teenage boy (Gyllenhaal) starts having freaky visions of a crazed, apocalypse-predicting bunny rabbit that compels him to commit crimes. It's great for trippy thrills or a costume for your next hipster Halloween party.

YOU AUGHTA KNOW:

Kelly wanted U2's "MLK" to play during the final sequence but couldn't get the rights, so he replaced it with Gary Jules's now beloved cover of the Tears for Fears song "Mad World."

68. Crouching Tiger, Hidden Dragon

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Released: 2000

Director: Ang Lee

Starring: Chow Yun-Fat, Michelle Yeoh, Zhang Ziyi, Chang Chen

After The Matrix popularized wildly-unrealistic fighting scenes (as choreographed by wire-work master Yuen Wo Ping), Ang Lee took it back to the motherland with this epic mix of fantasy and Chinese history. Come on haters, the flying is awesome.

YOU AUGHTA KNOW:

CTHD raked in $128 million in the U.S. alone, making it the highest-grossing foreign-language movie in American history.

67. Snatch

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Released: 2000

Director: Guy Ritchie

Starring: Benicio Del Toro, Brad Pitt, Jason Statham

Ritchie's Brit-heist follow-up to Lock, Stock and Two Smoking Barrels rounds up the usual blokes for some good old ultraviolence, including a scene-stealing turn from Pitt as an Irish boxer whose accent is so thick it got cast in a My Baby Got Back video. These Limeys are fucking grimy.

YOU AUGHTA KNOW:

Pitt asked for a role after loving Lock, Stock but he couldn't do a convincing London accent, so Ritchie made his character Irish.

66. The Pledge

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Released: 2001

Director: Sean Penn

Starring: Jack Nicholson, Robin Wright Penn, Benicio Del Toro, Aaron Eckhart, Mickey Rourke

A retired police detective (Nicholson) becomes obsessed with finding an elusive child molester and murderer after promising a victim's mother that he will bring them to justice. Like everything heavy in life, it goes tremendously with Prozac.

YOU AUGHTA KNOW:

The child murders depicted in the film were loosely based on actual cases that had been worked by Det. Joe Depczynski, the film's technical advisor, only they weren't thought to be the work of a lone serial killer.

65. Pan's Labyrinth

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Released: 2006

Director: Guillermo del Toro

Starring: Ivana Baquero, Doug Jones, Sergi López, Maribel Verdú

If studio's think Where The Wild Things Are is going to scare kids shitless, it's safe to assume they never sat down with Guillermo's twisted fantasy about a little Spanish girl who creates an alternate reality to escape the harsh realities of the Spanish Civil War. Keep this one in your back pocket if your lil' nephews ever need to be put in their place.

YOU AUGHTA KNOW:

Guillermo del Toro gave up his entire salary and bank end just to see the movie be made.

64. Minority Report

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Released: 2002

Director: Steven Spielberg

Starring: Tom Cruise, Colin Farrell

Spielberg's adaptation of the Philip K. Dick story brings to life a dystopian future in which "pre-crime" technology allows the police to stop murders before they happen. Whether it's for its stunning visuals or its deeper "fate vs. free will" subtext (or just for Tom Cruise being Tom Cruise), it's another S.S. masterpiece.

YOU AUGHTA KNOW:

The hand-controlled, open-air interface used by Cruise in the film was mimicked in ads for HP featuring Jay-Z and Pharrell (among others) in 2006.

63. Collateral

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Released: 2004

Director: Michael Mann

Starring: Jamie Foxx, Tom Cruise, Jada Pinkett Smith, Mark Ruffalo

In Michael Mann's dark crime thriller, Jamie Foxx plays a spineless cab driver forced to chauffeur Tom Cruise's mysterious, grey-haired assassin around on a night of cold-hearted contract killings. For once, it isn't Cruise's Scientological rants that make him scary.

YOU AUGHTA KNOW:

The movie was originally supposed to take place in New York before Michael Mann came on board and moved it to Los Angeles.

62. Friday Night Lights

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Released: 2004

Director: Peter Berg

Starring: Billy Bob Thornton, Lucas Black, Garrett Hedlund, Derek Luke, Jay Hernandez, Tim McGraw

Based on the true story of the 1988 Permian High School Panthers, this inspirational sports drama shows what it's like to play in an economically depressed Texas town where football is life and your best days are behind you after the final whistle. Welcome to the rest of your life!

YOU AUGHTA KNOW:

Buzz Bissinger, who wrote the book Friday Night Lights, famously beefed with Deadspin because he hates crass pseudo sports journalism (and hilarity).

61. Best in Show

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Released: 2000
Director: Christopher Guest
Starring: Christopher Guest, Parker Posey, Michael McKean, John Michael Higgins, Eugene Levy

A variety of dog-loving weirdos compete for glory at a national dog show in one of Guest's best mockumentaries. It's like This Is Spinal Tap (which Guest wrote and starred in) but with way more bitches!

YOU AUGHTA KNOW:
None of Guest's movies are scripted. The actors work know where the scene begins and ends and ad-lib the the rest.

60. The Wrestler

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Released: 2008

Director: Darren Aronofsky

Starring: Mickey Rourke, Marisa Tomei, Evan Rachel Wood

Rourke is phenomenal as an "old, broken down piece of meat" struggling to let go of a fading wrestling career while trying to reconnect with his estranged daughter. The melancholy moments are balanced by some surprisingly gruesome wrestling action-just consider Tomei's ageless stripper bod as the icing on the pierced nipple.

YOU AUGHTA KNOW:

Axl Rose allowed Aronofsky to use "Sweet Child O' Mine," which is Randy's entrance music for his final match, free of charge.

59. Munich

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Released: 2005

Director: Steven Spielberg

Starring: Eric Bana, Daniel Craig, Ciarán Hinds, Mathieu Kassovitz, Geoffrey Rush, Mathieu Amalric

Mossad agent Avner (Bana) leads a team on a black-ops mission to kill everyone involved in the 1972 Black September assassination of Israeli athletes at the Munich Olympics. Nebbish, these Jews are not.

YOU AUGHTA KNOW:

Guri Weinberg portrays his father, Moshe, who died in the Black September massacre when Guri was just one month old.

58. Fahrenheit 9/11

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Released: 2004

Director: Michael Moore

Starring: George W. Bush, Dick Cheney, Condoleeza Rice

Strong on left-wing views, Moore's documentary effectively exposed the shady dealings of the Bush Administration in relation to the 9/11 attacks. And unlike Bush, he makes his case using actual evidence!

YOU AUGHTA KNOW:

While they had original rights to the film, Disney refused to release it.

57. Drag Me to Hell

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Released: 2009
Director: Sam Raimi
Starring: Alison Lohman, Lorna Raver, Justin Long

When a bank employee (Lohman) denies a loan extension to an old gypsy lady (Raver) the nasty witch puts a curse on her. This shit is old school horror in the vein of Raimi's classic Evil Dead, with plenty of grossness but minus the excessive gore. You won't even miss it.

YOU AUGHTA KNOW:
Originally titled The Curse, the film's script was written by the Raimi brothers in the '90s, and then put on hold to do a little thing called Spider-Man.

56. Taken

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Released: 2008

Director: Pierre Morel

Starring: Liam Neeson, Maggie Grace, Famke Janssen

In this hard-hitting throwback tale of revenge, an ex-secret service agent (Neeson) uses his investigative and kill skills in a desperate attempt to save his teenage daughter from the Euro-thugs who abduct and drug her to sell her into sex slavery. And you thought a charm bracelet said "I love you, baby."

YOU AUGHTA KNOW:

The martial art form Neeson uses to kick ass is Nagasu Do, a hybrid of Judo, Aikido, and Ju Jitsu.

55. Open Water

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Released: 2003

Director: Chris Kentis

Starring: Blanchard Ryan, Daniel Travis

Imagine you and the lady go on a scuba diving trip and get stranded in the middle of the ocean with no land in sight. Being stuck with wifey for that long sounds bad enough, but we're not even factoring in the sharks on the prowl for fresh meat. And it's based on a true story. You'll never want to scuba dive after watching this one.

YOU AUGHTA KNOW:

Husband/wife team Chris Kentis and Laura Lau made the movie for $130,000 over the course of two-and-a-half years.

54. 25th Hour

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Released: 2002

Director: Spike Lee

Starring: Edward Norton, Philip Seymour Hoffman, Rosario Dawson, Brian Cox

If you had 24 hours of freedom, what would you do? We'd do some things we can't put in print. Ed Norton decides to spend his time with friends and family before heading to the bing to serve seven years for dealing drugs in this gritty Spike Lee joint. Remember kids: Drugs will do YOU!

YOU AUGHTA KNOW:

Tobey Maguire bought the rights to the movie with intent to star in it but decided to do Spider-Man 2.

53. Elf

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Released: 2003

Director: Jon Favreau

Starring: Will Ferrell, James Caan, Zooey Deschanel

The movie that jump-started Will Ferrell's career as a lead actor. This Christmas flick was more than suitable for children but had enough adult humor to keep the older heads satisfied. Plus it's funny enough to make even a Jew laugh!

YOU AUGHTA KNOW:

This screenplay was first shopped in 1993 and had Jim Carrey attached as the lead.

52. 300

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Released: 2006

Director: Zack Snyder

Starring: Gerard Butler, Lena Headey, Dominic West

Testosterone on celluloid is basically the only way to describe 300. Dumb, simple, and raw like an exposed bullet-wound, there are few movies that can get you mindlessly pumped for a little of the ultra-violence like 300. Rent this now and tonight you'll dine in hell!

YOU AUGHTA KNOW:

300 was based nearly shot-for-shot on Frank Miller's 1999 graphic novel of the same name.

51. Children Of Men

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Released: 2006

Director: Alfonso Cuarón

Starring: Clive Owen, Julianne Moore, Chiwetel Ejiofor, Michael Caine, Danny Huston

Abrupt and fiercely harsh, Cuarón's vision of a childless future was unrelenting in its bleak depiction of mankind, but endlessly satisfying in its detailed illustration of the future. It's nice to know we've got something to look forward to.

YOU AUGHTA KNOW:

The film was based on the 1994 P.D. James novel of the same name.

50. Paid in Full

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Released: 2002

Director: Charles Stone III

Starring: Wood Harris, Cameron "Cam'ron" Giles, Mekhi Phifer

What you know about that 1985 cocaine flow? Although produced by Roc-A-Fella Films, Paid in Full is nothing like State Property. Dame Dash enlists the director of Drumline to tell the fictionalized story of Harlem's big time '80s coke pushers. Drop-top Saabs, velour suits, and gold rope chains all make cameos.

YOU AUGHTA KNOW:

Although it's an '80s period piece, extras regularly appear wearing conspicuously baggy modern jeans and Tims.

49. High Tension

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Released: 2003
Director: Alexandre Aja
Starring: Cécile De France, Maïwenn Le Besco, Philippe Nahon

While visiting relatives in the countryside, two French college chicks (De France and Le Besco) encounter a sadistic, mutilating serial killer. It's nice to know that other countries are just as twisted as we are.

YOU AUGHTA KNOW:
Renowned Italian horror make-up artist Giannetto De Rossi did all the movie's gory effects, including a decapitation via bookcase that had to be cut for an R-rating in the U.S.

48. Sin Nombre

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Released: 2009

Director: Cary Joji Fukunaga

Starring: Paulina Gaitán, Edgar Flores, Kristyan Ferrer, Tenoch Huerta Mejía

This poignant and violent drama follows a Honduran teenager (Gaitán) in search of a better life and a runaway Mexican gang member (Flores) who's being hunted by his old homeboys as they cross paths while riding atop trains to the U.S. border. It's a gang-banger!

YOU AUGHTA KNOW:

Fukunaga had a former gang member edit his script to make it as realistic as possible.

47. 8 Mile

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Released: 2002

Director: Curtis Hanson

Starring: Eminem, Mekhi Phifer, Brittany Murphy, Kim Basinger

Eminem's polished, emotive biopic transformed him from national scourge to national hero and brilliantly demonstated the rhyme-writing process, legitimizing the art form in the eyes of Middle America. Because real hip-hop gives a shit what Middle America thinks of it.

YOU AUGHTA KNOW:

"Lose Yourself" from the movie's soundtrack won an Oscar.

46. Spirited Away

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Released: 2001

Director: Hayao Miyazaki

Starring: Daveigh Chase, Jason Marsden, Suzanne Pleshette

When a girl's parents get turned into pigs, she's forced to work in a magical bathhouse for spirits. Miyazaki, the god of Japanese fantasy, managed to top his previous animated masterpieces with this fairytale that's dark and weird enough for the whole family.

YOU AUGHTA KNOW:

In Japan, Spirited Away is the highest-grossing film of all time.

45. Raising Victor Vargas

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Released: 2002

Director: Peter Sollett

Starring: Victor Rasuk, Judy Marte, Melonie Diaz

We all love Kids for its comical glorification of NYC teenagers, but to us, Raising Victor Vargas feels a lot more authentic. The sweet (not sappy) story of adolescent love is also an ode to the Lower East Side—the real L.E.S., minus the misanthropic gerbils who hang out at Supreme.

YOU AUGHTA KNOW:

The original title of the movie was Long Way Home, which sounds like a bad Kevin Costner rom-com.

44. Wet Hot American Summer

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Released: 2001

Director: David Wain

Starring: Michael Showalter, Janeane Garofolo, Paul Rudd, David Hyde Pierce, Christopher Meloni, Molly Shannon, Ken Marino, Amy Poehler

A hilarious ensemble cast (including half of MTV's The State) shine in this absurdist parody of '80s summer camp movies like Meatballs. With 30-year-olds playing teenage counselors and a talking can of creamed corn, this flick thrives on not making sense.

YOU AUGHTA KNOW:

Critic Roger Ebert hated this movie so much that he wrote a song about it. Seriously.

43. The Incredibles

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Released: 2004

Director: Brad Bird

Starring: Craig T. Nelson, Holly Hunter, Jason Lee, Samuel L. Jackson

Sure, there are animated movies with more artistic cred but Pixar managed to tell a good story about a family of retired superheroes, kick ass, AND give you lifelong fantasies starring Holly Hunter as the most flexible woman in the world. The mind reels.

YOU AUGHTA KNOW:

The makers of The Fantastic Four, which came out the next year, were forced to change their movie considerably due to plot similarities with The Incredibles. Maybe that's why it sucked.

42. Casino Royale

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Released: 2006
Director: Martin Campbell
Starring: Daniel Craig, Jeffery Wright, Eva Green, Judi Dench

James Bond hasn't been the same since Sean Connery was 007. Thankfully Daniel Craig brings some balls back to Britain's favorite secret agent with crazy aerial stunts, killer fight scenes, and, of course, a dime piece waiting to be the holster to his pistol. We're glad he's back to his old self.

YOU AUGHTA KNOW:
Casino Royale is the first James Bond movie in 27 years to be based on an Ian Flemming novel.

41. Traffic

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Released: 2000

Director: Steven Soderbergh

Starring: Benicio Del Toro, Don Cheadle, Michael Douglas, Catherine Zeta-Jones, Dennis Quaid

The war on drugs has been going on a lot longer than the one in Iraq, and it might be just as futile. A huge ensemble cast goes in on every aspect of it (users, cops, dealers, and politicians) and somehow makes two-and-a-half hours go by quicker than a nitrous high. Or so we hear.

YOU AUGHTA KNOW:

Both the DEA and the Customs Department helped point out inaccuracies in the script, even granted the crew access to a Mexico border checkpoint for filming.

40. X2: X-Men United

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Released: 2003

Director: Bryan Singer

Starring: Hugh Jackman, Halle Berry, James Marsden, Anna Paquin, Patrick Stewart, Ian McKellen, Famke Janssen, Brian Cox

After a well-received, but lackluster first run, Singer and the merry mutants took it back to the lab and introduced fan favorites like Nightcrawler, invoking classic Chris Claremont storylines from the '70s comics. Oh, and they made the whole mutant thing an analogy for being gay. Not that there's anything wrong with that.

YOU AUGHTA KNOW:

Ian McKellen admitted on a late-night talk show that he hadn't watched X2 until years after the film's release—and that he quite enjoyed it.

39. Grandma's Boy

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Released: 2006

Director: Nicholaus Goossen

Starring: Allen Covert, Linda Cardellini

This joint, featuring all of Adam Sandler's recurrent background players, may actually rival the Hanukkah-celebrating-comedian's best for raw hilarity. Whether it's Allen Covert busting off on Nick Swardson's mom or Linda Cardellini's "Push It" karaoke, Grandma's Boy is brimming with laugh-til-you-cry moments. Shit's (not) wiz-eak!

YOU AUGHTA KNOW:

The video game featured in the film, Demonik, was actually set to be released, but the production company fell into financial troubles before the game was finished.

38. Eastern Promises

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Released: 2007

Director: David Cronenberg

Starring: Viggo Mortensen, Naomi Watts, Vincent Cassel, Armin Mueller-Stahl

You won't find a more thorough badass than Viggo's Nikolai Luzhin, the henchman for a Russian mob family in London. Dude will break your face just for breathing, don't matter if it's the streets or the steam room. We haven't been more entertained by an all-male nude Turkish bath scene since...well, ever.

YOU AUGHTA KNOW:

Viggo's character is covered in gang tattoos, including two on opposite ankles that read: "Where are you going?" and "What the fuck do you care?" Which would be even doper if "Because I'm fucking your mother" was tattooed across his toes.

37. Murderball

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Released: 2005

Director: Henry Alex Rubin, Dana Adam Shapiro

Starring: Mark Zupan, Keith Cavill

This sports documentary follows quadriplegics who play full-contact wheelchair rugby, a.k.a. Murderball, and compete in the Paralympic Games in Athens, Greece. If ever you need motivation to get up off of your ass, this movie's got you.

YOU AUGHTA KNOW:

Murderball was invented in Canada in 1977 because quadriplegics don't have full use of their hands and arms to play wheelchair basketball.

36. Dawn of the Dead

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Released: 2004

Director: Zack Snyder

Starring: Sarah Polley, Ving Rhames, Mekhi Phifer, Jake Weber, Michael Kelly

In this remake of George A. Romero's 1978 horror classic, strangers seek refuge in a shopping mall while the blood-thirsty reanimated dead gather outside. It's like Black Friday with zombies!

YOU AUGHTA KNOW:

Starbucks, which regularly extorts coffee-crazed zombies, refused to let its name be used in the mall. Too close to home.

35. Baby Boy

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Released: 2001

Director: John Singleton

Starring: Tyrese Gibson, Taraji P. Henson, Snoop Dogg, Ving Rhames

This unintentionally hilarious classic plays like a parody of '90s West Coast hood dramas, only Singleton (who defined the genre with Boyz N The Hood) is dead serious. With some of the greatest over-acting of all time, Black Ty was really going for Oscar gold.

YOU AUGHTA KNOW:

Singleton originally wrote the lead role for Tupac.

34. Blow

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Released: 2001

Director: Ted Demme

Starring: Johnny Depp, Penelope Cruz, Ray Liotta

Forget your favorite rapper's coke tales. Blow laid out the true story of original hustler George Jung, who hooked up with some Colombian guy named Pablo Escobar (you may have heard of him) and helped establish America's cocaine market in the '70s. So dope it'll make your nose bleed.

YOU AUGHTA KNOW:

Actors snorted milk powder during scenes with cocaine.

33. The Hurt Locker

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Released: 2008

Director: Kathryn Bigelow

Starring: Jeremy Renner, Anthony Mackie, Brian Geraghty, Guy Pearce, Ralph Fiennes, David Morse, Evangeline Lilly

A highly trained bomb disposal team in Iraq struggles with a new sergeant (Renner), who appears to be a reckless adrenaline junkie. If this taut, well-paced war thriller doesn't make your pulse race, you must be flatlining.

YOU AUGHTA KNOW:

The movie is based on the accounts of Mark Boal, a freelance journalist who was embedded with an American bomb squad in the war in Iraq.

32. Knocked Up

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Released: 2007

Director: Judd Apatow

Starring: Seth Rogen, Katherine Heigl, Jonah Hill, Paul Rudd, Jason Segel, Jay Baruchel

This reproduction riot established Judd Apatow and his crew, including Complex cover stars Seth Rogen and Jonah Hill, as a real force in Hollywood. Partially based on the birth of Apatow's first daughter, it grossed over $200 million worldwide. Daddy like.

YOU AUGHTA KNOW:

The word "fuck" is said 120 times in the movie. And yet we still bring children into this world.

31. Mystic River

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Released: 2003

Director: Clint Eastwood

Starring: Kevin Bacon, Sean Penn, Tim Robbins

Three childhood best friends grow up to be all kinds of fucked up, then have to deal with a bunch more fucked-up shit. Like, fuck. Really doe, this is Eastwood at his best—directing a movie that doesn't star him. Cops, murder, and psychological scars—it's what Boston does best!

YOU AUGHTA KNOW:

The Longfellow poem "Paul Revere's Ride" takes place along the banks of the Mystic River. Heh, you said "Longfellow."

30. Almost Famous

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Released: 2000

Director: Cameron Crowe

Starring: Patrick Fugit, Kate Hudson, Billy Crudup, Jason Lee, Zooey Deschanel, Anna Paquin, Phillip Seymour Hoffman

In Crowe's semi-autobiographical account of life as a young Rolling Stone reporter, a nerdy, 15-year-old music geek (Fugit) gets hired to follow the rock group Stillwater on tour. Rock dreams come true as hotels are trashed, virginity is lost to groupies, and drugs are done. And they say it's the devil's music.

YOU AUGHTA KNOW:

Rock legend Peter Frampton wrote all of Stillwater's songs with Cameron Crowe and his rocking wife Nancy Wilson. He also taught Billy Crudup to play guitar for his concert scenes.

29. Old School

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Released: 2003

Director: Todd Phillips

Starring: Luke Wilson, Vince Vaughn, Will Ferrell, Jeremy Piven, Elisha Cuthbert

Three 30-somethings hit a rough patch in life and decide that re-living their college fraternity days will help them sort things out. And it does, of course, because all of life's answers can be found in a coed or at the bottom of a Jäger shot.

YOU AUGHTA KNOW:

A sequel was written but turned down by the original stars.

28. Gladiator

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Released: 2000

Director: Ridley Scott

Starring: Russell Crowe, Joaquin Phoenix, Connie Nielsen

A brawny general-turned-prisoner, a freakshow emperor with daddy issues, and a motley crew of bruisers and slaves pre-enact Bloodsport in the Colosseum. Sure, it's a great film—but more importantly, it's a kick-ass movie.

YOU AUGHTA KNOW:

After Oliver Reed (who played the gladiator Proximo) died during filming, a CGI company mapped a 3-D mask of his face onto a live-action body double for all the posthumously filmed fight scenes.

27. Cocaine Cowboys

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Released: 2006

Director: Billy Corben

Starring: Jon Roberts, Mickey Munday, Jorge "Rivi" Ayala

Scarface was cool, yeah, but Corben's documentary featuring some of Miami's biggest snowmen tells you what really went down in the '70s and '80s when the economy was shit but successful drug runners were copping whips and crashing them for fun. And there's no fake Cuban accents, either.

YOU AUGHTA KNOW:

HBO is planning a series based on the documentary.

26. District 9

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Released: 2009

Director: Neill Blomkamp 

Starring: Sharlto Copley, Jason Cope, Robert Hobbs

In this sensational sci-fi smash, humans welcome aliens to Johannesburg, South Africa by putting them in slums, getting them strung out on cat food, and secretly experimenting on them to steal their weapons technology. On the bright side, human-on-human oppression is way down!

YOU AUGHTA KNOW:

The film is based on Blomkamp's documentary-style 2005 short Alive in Joburg, which depicted tense social interaction between aliens and humans in Johannesburg, South Africa.

25. Sin City

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Released: 2005

Director: Robert Rodriguez, Frank Miller

Starring: Jessica Alba, Mickey Rourke, Bruce Willis, Clive Owen, Rosario Dawson, Benicio Del Toro, Carla Gugino, Elijah Wood, Nick Stahl, Brittany Murphy

One of the illest comic books ever gets the frame-for-frame treatment by its own creator, Frank Miller, and it more than makes up for pap like The Spirit. Vigilante justice, serial killers, and the sublime beauty of an amoral society. Wow, that sounded like a term paper we bought off the Internet.

YOU AUGHTA KNOW:

Despite the extensive CGI in the movie, Mickey Rourke still needed three hours of old-fashioned makeup every day for his comeback role as Marv the hitman.

24. Requiem for a Dream

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Released: 2000

Director: Darren Aronofsky

Starring: Jennifer Connelly, Jared Leto, Marlon Wayans, Ellen Burstyn

Drugs are fun, aren't they? Especially when you develop a huge disgusting abscess, or your best friend gets locked up, or your girlfriend ends up doing double-ended dildo sex shows to get heroin, or your diet pill junkie mom winds up catatonic in the nuthouse. Yeeeeah, awesome.

YOU AUGHTA KNOW:

Hubert Selby Jr., who wrote the book the movie is based on, makes a cameo as a prison officer.

23. Harold & Kumar Go to White Castle

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Released: 2004

Director: Danny Leiner

Starring: John Cho, Kal Penn, Neil Patrick Harris, Paula Garces, Anthony Anderson, Christopher Meloni, Malin Ackerman

Finally, Korean- and Indian-American dudes got a movie that didn't depict them as grocery owners or taxi drivers. H&K, two regular-ass stoners on a super-specific munchies mission for the lil' burger you love to ate, are the most trailblazing tree blazers ever. Respect due.

YOU AUGHTA KNOW:

A third film in the franchise, A Very Harold and Kumar Christmas, has been slated for a November 2010 release.

22. There Will Be Blood

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Released: 2007

Director: Paul Thomas Anderson

Starring: Daniel Day-Lewis, Paul Dano

This sweeping epic about the treachery and hardships that plagued the American oil industry in its early days earned P.T.A. a couple award show appearances. But all you need to know is that Daniel Day-Lewis killed it and he will drink your milkshake. No pause.

YOU AUGHTA KNOW:

The main character Daniel Plainview was modeled loosely on famous oil man Edward Doheny and his characteristics were based on Count Dracula.

21. Training Day

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Released: 2001

Director: Antoine Fuqua

Starring: Denzel Washington, Ethan Hawke, Eva Mendes, Snoop Dogg, Scott Glenn

We've gotten past the fact that it took Denzel having to play a gloriously ruthless and morally bankrupt LAPD detective for him to bring home a Best Actor Oscar. Mainly due to the fact that we got to see Eva Mendes naked, Ethan Hawke (as Denzel's rookie partner) smoke dust, and Snoop Dogg try to evade the cops in a wheel chair.

YOU AUGHTA KNOW:

T. Rodgers, the founder of the Black P. Stones Bloods in Baldwin Village a.k.a. The Jungles in Los Angeles, was on set for all of the filming in his neighborhood and allowed the producers to use his neighborhood in exchange for casting gang members.

20. The Believer

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Released: 2001

Director: Henry Bean

Starring: Ryan Gosling, Billy Zane, Summer Phoenix

You know who makes the illest Neo-Nazis? You guessed it: Jewish yeshiva students! Somehow Gosling makes the paradox plausible, though we have to say that giving the head Nazi the last name Zampf is about as imaginative as naming him Hatler.

YOU AUGHTA KNOW:

The movie's based on an actual Klansman in the '60s who was discovered to be Jewish (except in real life, homie killed himself).

19. Oldboy

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Released: 2003

Director: Park Chan-wook

Starring: Choi Min-Sik, Yu Ji-Tae, Kang Hye-Jeong

The ultimate revenge movie begins when a businessman is locked in an anonymous hotel room for 15 years with no explanation. After getting released, he sets off on a violent, twisted quest to uncover the mystery of his captor and his motivation.

YOU AUGHTA KNOW:

Spielberg and Will Smith are doing a remake, but there probably won't be any eating of live octopus.

18. Eternal Sunshine of the Spotless Mind

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Released: 2004

Director: Michel Gondry

Starring: Kate Winslet, Jim Carrey, Kirsten Dunst, Elijah Wood, Mark Ruffalo

A smelly-looking white couple breaks up, then tries to erase their memories of each another. The words "postmodern romantic dramedy" are horrible, sure, but they can also be used to describe a great movie. And with Gondry directing and Jon Brion doing the score, this is like a two-hour version of "Videos Kanye West Wishes He Had Made."

YOU AUGHTA KNOW:

Jay Electronica sampled the movie on his track "Act 1: Eternal Sunshine (The Pledge)." No, we haven't either.

17. Zoolander

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Released: 2001

Director: Ben Stiller

Starring: Ben Stiller, Owen Wilson, Will Ferrell, Jerry Stiller, Christine Taylor

This send-up of the fashion industry is the definitive Ben Stiller comedy (if you disagree, please Derelicte our balls). It was also a huge breakout role for Will Ferrell, who almost steals the show from Stiller and Owen Wilson's hilarious male model duo as the bitchy designer Mugatu.

YOU AUGHTA KNOW:

Rumor has it that Stiller lifted parts of the story from Bret Easton Ellis's novel Glamorama. Ellis has said he can't discuss it because of a "settlement."

16. Ocean's Eleven

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Released: 2001

Director: Steven Soderbergh

Starring: George Clooney, Brad Pitt, Matt Damon, Bernie Mack, Don Cheadle, Casey Affleck, Scott Caan, Andy Garcia, Julia Roberts

Clooney, Pitt, and a lot of other cool mofos play a crew of cons who plan a brazen heist of a bunch of Vegas casinos. Sure, the film is as lightweight as Manny Pacquiao but like Pac-Man, it's also endlessly entertaining.

YOU AUGHTA KNOW:

Brad Pitt is eating in almost every scene. Food, that is.

15. Star Trek

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Released: 2009

Director: J.J. Abrams

Starring: Chris Pine, Zachary Quinto, Eric Bana, Zoe Saldana, Karl Urban, Simon Pegg, Leonard Nimoy, John Cho, Anton Yelchin, Winona Ryder, Bruce Greenwood

Young James Tiberius Kirk (Pine) and the crew of the U.S.S. Enterprise fight to protect the universe from the time-traveling Romulan terrorist (Bana) who killed Kirk's father and altered the time-space continuum. This unrelenting space jam will get up in Uranus for real.

YOU AUGHTA KNOW:

Rather than do an imitation of William Shatner's melodramatic ass, Pine based his Kirk on Tom Cruise's Maverick and Harrison Ford's Han Solo and Indiana Jones.

14. Borat

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Released: 2006

Director: Larry Charles

Starring: Sacha Baron Cohen, Ken Davitian, Luenell, Pamela Anderson

Disguised as a sexist, homophobic, anti-Semitic Kazakh journalist, Baron Cohen interacts with unsuspecting citizens and exposes American xenophobia, homophobia, and racism. Hey, did you know we're a country of backwards morons? Niiiiice!

YOU AUGHTA KNOW:

Sacha Baron Cohen avoided doing a sequel because the Borat character had become too well known to pull off pranks undetected.

13. Superbad

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Released: 2007

Director: Greg Mottola

Starring: Jonah Hill, Michael Cera, Seth Rogen, Bill Hader

The story of two best friends at the end of their high school adventure, Superbad finds the Apatow machine at its peak, operating without fear of failure or creative binds. Hilarious, real, and touching, this is a perfect piece of comedic cinema...to draw a dick on!

YOU AUGHTA KNOW:

Seth Rogen and partner Evan Goldberg began writing Superbad at age 13.

12. American Psycho

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Released: 2000

Director: Mary Harron

Starring: Christian Bale, Jared Leto, Chloë Sevigny

In this adaptation of the classic '80s novel by Bret Easton Ellis, Bale goes rogue as a murderous i-banker who hides his bloodlust behind a mask of sanity. Skewers the excess of conspicuous consumption so heartily you almost wish rappers would get the hint.

YOU AUGHTA KNOW:

Kanye West's video for "Love Lockdown" was inspired by the movie. So rappers did get the hint!

11. Kill Bill, Vol. 1

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Released: 2003

Director: Quentin Tarantino

Starring: Uma Thurman, Lucy Liu, David Carradine, Vivica Fox, Daryl Hannah, Michael Madsen

The first volume of QT's fantastically twisted samurai epic has better (and bloodier) girl-on-girl action than your favorite spankwire.com clip. Every character is memorable, each death scene is awesome, and the dialogue is...well, it's Tarantino.

YOU AUGHTA KNOW:

Rumors abound about the planned third and fourth volumes of the Kill Bill series; QT has said that Vol. 3 will focus on the daughter of a man killed by The Bride. Anticipated release date? According to a Tarantino interview in '04: 2019.

10. No Country for Old Men

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Released: 2007

Director: Ethan & Joel Coen

Starring: Josh Brolin, Javier Bardem, Tommy Lee Jones

When an ordinary Texas Joe (Brolin) happens upon a drug deal gone bad, he takes off with the $2.4 million in cash. In pursuit are a psychotic hitman (Bardem) trying to murk him and a grizzled sheriff (Jones) trying to protect him. Cormac McCarthy's novel is equally dope and nerve-wracking, but who actually reads books in 2009?

YOU AUGHTA KNOW:

To off his victims, Bardem's character uses a captive bolt pistol usually used to stun cattle before they're slaughtered. Holy cow!

9. The Departed

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Released: 2006

Director: Martin Scorsese

Starring: Matt Damon, Leonardo DiCaprio, Jack Nicholson, Martin Sheen, Mark Wahlberg, Alec Baldwin

With source material as dope as the Hong Kong classic Infernal Affairs, Scorsese's take on the cop-gangster switcheroo could hardly fail. But with DiCaprio and Damon at their best—and Mark Wahlberg and Alec Baldwin stealing every scene they're in—the remake is even better than the O.G.

YOU AUGHTA KNOW:

According to imdb.com, this movie has the most uses of the word "fuck" (and its derivatives) to win the Best Picture Oscar. That's 237 fucking times, if you're counting.

8. The Bourne Ultimatum

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Released: 2007

Director: Paul Greengrass

Starring: Matt Damon, Julia Stiles, Joan Allen, Albert Finney, David Strathairn, Scott Glenn, Édgar Ramírez

Former CIA assassin and amnesiac Jason Bourne (Damon) comes out of hiding to finally uncover all the secrets of his shadowy past while avoiding hitmen sent by his former government handlers. This is the best of the griitty spy series that left James Bond shaken and stirred.

YOU AUGHTA KNOW:

During filming of the climactic chase scene in Manhattan, speeds never exceeded 35 mph because of the NYPD's safety concerns. Slow your roll!

7. Memento

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Released: 2000

Director: Christopher Nolan

Starring: Guy Pearce, Carrie-Anne Moss, Joe Pantoliano

In Nolan's pre-Batman banger, a guy with no short-term memory (Pearce) hunts for his wife's killers with the help of his own tattoos. Oh, and the story is told backwards, so you feel just as mind-fucked as he does.

YOU AUGHTA KNOW:

After Miramax's Harvey Weinstein passed on distributing the movie—and it turned out to be a cult hit—he tried to buy it from the distributor after the fact. You lose, Miramax!

6. The Dark Knight

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Released: 2008

Director: Christopher Nolan

Starring: Christian Bale, Aaron Eckhart, Heath Ledger, Maggie Gyllenhaal, Michael Caine

Nolan's dark and unrelenting follow-up to Batman Begins pits Bale's gravelly voiced Cape Crusader against one of the best movie villains ever: Heath Ledger's maniacal Joker. Sadly, he won't reprise the role, but on the bright side Maggie Gyllenhaal won't be back either.

YOU AUGHTA KNOW:

The Dark Knight is the first Batman film to not have "Batman" in the title.

5. City of God

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Released: 2002

Director: Fernando Meirelles, Kátia Lund

Starring: Alexandre Rodrigues, Alice Braga, Leandro Firmino, Phellipe Haagensen, Douglas Silva

This beautifully shot and skillfully acted crime drama tells the story of a young aspiring photographer caught in the middle of the drugs and violence that run rampant in his poor Rio de Janeiro neighborhood. Listen up, Capo: Real gangsters do wear flip-flops.

YOU AUGHTA KNOW:

Although based on the gritty Cidade de Deus slum, the movie was shot in a neighboring, less dangerous, neighborhood.

4. The 40 Year-Old Virgin

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Released: 2005

Director: Judd Apatow

Starring: Steve Carell, Romany Malco, Seth Rogen, Paul Rudd, Catherine Keener

The movie that turned Judd Apatow from failed TV producer into film comedy god is two solid hours of hilarious jokes on a can't-beat premise, and that's not counting the awesome outtakes. You know we know you're gay if you didn't cut for this flick.

YOU AUGHTA KNOW:

Rogen rocks T-shirts with the covers of Public Enemy's Fear of a Black Planet and GZA's Liquid Swords in the movie.

3. 28 Days Later

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Released: 2002

Director: Danny Boyle

Starring: Cillian Murphy, Naomie Harris, Brendan Gleeson, Christopher Eccleston

Imagine waking from a coma, going outside into seemingly deserted London, and being chased by a crazed mob of people infected with an incurable rage virus who want to do nothing more than tear you to shreds. And you thought New Yorkers were standoffish.

YOU AUGHTA KNOW:

Horror god Stephen King bought out an entire showing of the film in New York City, so you know it's good.

2. Iron Man

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Released: 2008

Director: Jon Favreau

Starring: Robert Downey, Jr., Terrence Howard, Gwyneth Paltrow

Finally, a movie that brought Iron Man's kick-ass persona to a mainstream audience. One of the best superhero movies of all time helped Robert Downey, Jr. reach heights he hadn't experienced since crack rock.

YOU AUGHTA KNOW:

Favreau commissioned star comic book writers Mark Millar, Brian Bendis, Joe Quesada, Tom Brevoort, Axel Alonzo, and Ralph Macchio (not the Karate Kid one) to give advice on the script.

1. Anchorman: The Legend of Ron Burgundy

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Released: 2000

Director: Adam McKay

Starring: Will Ferrell, Christina Applegate, Paul Rudd, Steve Carell

Will Ferrell is at his absolute best playing a dim-witted, chauvinistic TV reporter fighting workplace gender equality in this send-up of ‘70s culture. With its countless quotables, Anchorman makes other comedies smell like a used diaper filled with Indian food.

YOU AUGHTA KNOW:

Anchorman 2: The Legend was release in 2013 –  and is set in the ‘80s.

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