The 100 Best Lil Wayne Songs

We count down the best songs from Weezy F. Baby.

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Complex Original

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Lil Wayne's rise from scrappy New Orleanian underdog to one of rap's biggest stars (and easily one of its most talented) has been a slow one. Inducted to the Cash Money family while still a young teen, the MC trained under some of Southern rap's greatest spitters.

In the time since, we've seen him embrace many roles: the hyperactive teenage soldier; the blinging bounce-rap hookmaster; the mixtape assassin; the syrup-sippin' space cadet experimentalist; the Auto-Tuned pop-rap heartthrob; and the wannabe rock star.

From a distance, these creative periods seem disparate, if not completely schizophrenic, but the evolution makes sense when you look at his enormous body of work as a whole. At his best, Weezy is all of these things at once, a jack of all trades and a master of most. As he emerges from his much publicized Riker's Island stay, Complex jumped headfirst into Wayne's seemingly infinite discography to select The 100 Best Lil Wayne Songs...

Listen to Complex's Lil Wayne playlists here: YouTube/Spotify/Rdio

Written by Andrew Noz (@noz)

This story originally appeared in altered form on November 3, 2010.

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100. Lil Wayne "Gossip" (2007)

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Producer: StreetRunner

Album: The Leak

Label: Cash Money



Grabbing its hook from a spoken interlude off an obscure cover of "Stop In The Name Of Love," "Gossip" catches Wayne calling out those that hate, criticize, and...analyze him. Hating and criticism we get, but dude is really mad at a mere analysis. What if it's a positive analysis? Regardless this record came at a time when Wayne was subject to a lot of scrutiny within the hip-hop community and he addressed it accordingly on his closing line-calling himself "Mr. Hip-Hop" and declaring "I'm not dead, I'm alive" as a resuscitated pulse monitor resumes beating.

99. Lil Wayne f/ Mack Maine & Raw Dizzy "Ride With The Mac" (2006)

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98. B.G.'z "From Tha 13th To Tha 17th" (1995)

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97. Birdman f/ Lil Wayne & Mack Maine "Always Strapped" (2006)

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Producer: Mr. Beatz
Album: Pricele$$
Label: Cash Money, Universal Motown


Squawk! Baby tricked you into thinking that this was going to be a Rebirth-style rap rock with that opening guitar riff. But the thrash quickly fades away in favor of a synth-horn driven thumper. The subject matter for a Baby and Wayne single is always predictable-a decadent jump into a world of rims, guns, and hoes, sprinkled with just enough of Wayne's oddball free association (here he's going on about vanilla pudding and polka dots)-but it's just so damn effective.

96. Lil Wayne f/ Hot Boys "Shine" (2000)

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95. Juvenile f/ Lil Wayne "G-Code" (1999)

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Producer: Mannie Fresh

Album: Tha G-Code

Label: Cash Money, Universal


Wayne may have been just a teen in the Hot Boys days, but he had the mind (and raps) of an old soul. Or at least an old convict-every verse was a more violent and elaborate heist than the last. And they were always action-oriented too, as he best illustrates with the giant string of verbs on Juve's "G-Code." He was runnin', hidin', duckin', stuntin', ridin', thuggin', dumpin' fire, bustin', lovin', lyin', lustin', stealin', killin', rapin', runnin' (again), climbin', chasin', strugglin', and hustlin' to make it. The verse could make for a great elementary school lesson in continuous tenses if it weren't for all the rapin' and stealin' and such.

94. Cassidy f/ Lil Wayne & Fabolous "6 Minutes" (2005)

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93. Lil Wayne f/ Big Tymers & TQ "Way of Life" (2002)

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Producer: Mannie Fresh
Album: 500 Degreez
Label: Cash Money

Once again showing their nostalgic side, Wayne and the Big Tymers re-purposed the same Dennis Edwards beat that Eric B. and Rakim first popularized with "Paid In Full." "Way of Life" not only works as yet another link on the long chain of materialistic Cash Money party starters, but as a testament that maybe the rap generational gap isn't as wide as some might think. Wayne's Benz fins are fished out, much like Ra's favorite dish was.

92. Lil Wayne "Help" (2007)

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91. T-Pain f/ Lil Wayne "Can't Believe It" (2008)

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Producer: T-Pain
Album: Thr33 Ringz
Label: Nappy Boy, Konvict, Jive

It was a defining move when Wayne took the plunge into the Auto-Tune, but it was T-Pain who first popularized the style and likely inspired Wayne's departure. So it only made sense for Teddy to call on him to return the favor by kicking a verse on his Snap&B favorite. Both of them are appropriately drenched in the vocal effect with their fractals of robot burps filling all the empty space in the airy track.

90. Lil Wayne f/ Mack Maine "Zoo" (2007)

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89. Lil Wayne "Where You At" (2002)

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88. Birdman f/ Lil Wayne "Neck of the Woods" (2005)

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Producer: Batman

Album: Fast Money

Label: Cash Money


Wayne and his stand-in pops take you to their neck of the woods where guns go "kak kak kak" and general mayhem reigns. The duo's intimidation tactics are intensified by the virtually unknown, but awesomely named CMR producer Batman, who turns a classic Barry White break into something more sinister.

87. Young Money "Every Girl" (2009)

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Producer: Tha Bizness
Album: We Are Young Money
Label: Young Money, Cash Money, Universal Motown

On Young Money's coming-out party single, Wayne opens with a heavily Auto-Tuned verse outlining the many highlights in his quest to "fuck every girl in the world." The hook took on a more insidious meaning and sparked a small controversy when Young Money unwittingly brought Wayne's daughter and several of her pre-teen friends on stage to dance during their performance of the song at last year's BET Awards. Whoops! Not those girls, just the legal ones. (Though Mack Maine isn't so discriminating when it comes to the mentally handicapped, as he brags of exchanging "V Cards with the retards.")

86. Sqad Up "Hollygrove" (2003)

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85. Lil Wayne "I'm A Beast" (2007)

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84. Gorilla Zoe f/ Lil Wayne "Lost" (2009)

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83. Lil Wayne "Run This Town Freestyle" (2009)

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82. Drake f/ Lil Wayne & Young Jeezy "I'm Goin' In" (2009)

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Producer: Needlz

Album: So Far Gone EP

Label: Young Money, Cash Money, Universal Motown


Making a late addition to the commercial EP version of his acclaimed So Far Gone mixtape, Drake brought Weezy and Jeezy along for support when "Goin In." In both rap style and attitude Wayne is almost perfectly equidistant between Jeezy's snarl and Drake's sensitivity and that balance might account for his scene stealing lead-off verse. It's not only "so official that all he needs is a whistle," it's compelling enough that a DJ could probably spin it back a few times before even getting to Drizzy or Jeezy. They should have known better than to give Wayne the opening bars.

81. Lil Wayne And Juelz Santana "Welcome To The Concrete Jungle" (2006)

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Producer: Clayton Haraba

Album: Dedication 2

Label: N/A


One of the stronger outings from the "Can't Feel My Face" brothers. Juelz runs with a more direct interpretation of the "Concrete Jungle" theme, telling of blocks with de-muzzled lions while Wayne offers up one of his more intricate verses, featuring this subtly clever switch-up: "I ain't shooting at your soldiers, bitch, I'm going for the captain/I ain't shooting at your shoulders, bitch, I'm going for the cap, and/I won't stop cappin'/'til your wings stop flapping." He then rolls with that angelic theme from there on out, leaving foes-and listeners-with a heavenly feel.

80. Rick Ross f/ T-Pain, Lil Wayne & Kanye West "Maybach Music 2" (2009)

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Producer: J.U.S.T.I.C.E. League

Album: Deeper Than Rap

Label: Maybach, Slip-n-Slide, Def Jam


The second installment in Rozay's "Maybach" series has a weirdly scatalogical bent. Kanye brags about pooping on things (metaphorically) but it's Wanye's unforgettable verse opener-"All black Maybach/I'm sitting in the asshole"-that truly set off the Pause Police alarms. Thankfully, Weezy's Fresh Prince punchlines and Justice League's grandiose track more than compensate for those brief lyrical lapses.

79. Sqad Up "Hoes, Hoes, Hoes" (2002)

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78. Lil Wayne f/ Pharrell "Yes" (2009)

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77. Lil Wayne "Georgia Bush" (2006)

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76. Lil Wayne f/ Birdman "We Don't" (2004)

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Producer: Mannie Fresh

Album: Tha Carter

Label: Cash Money, Universal


Wayne brings his usual ski-mask-way bravado on "We Don't," but there's something special in the way he just just slides into Mannie's beat: "The murder man/Picture me lurkin/Right up behind ya curtains/Nine's squirtin'." The hook still sounds hard to this day, despite the lingering presence of Snoop-inspired fizzuck-bizzuck speak, and even Birdman delivers an unexpectedly dexterous contribution.

75. Lil Wayne f/ D. Smith "Shoot Me Down" (2008)

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Producer: D. Smith

Album: Tha Carter III

Label: Cash Money, Universal Motown


Feeling like the spiritual successor to Tha Carter II's "Shooter," "Shoot Me Down" is another heavy-handed and lumbering beat (with actual live instrumentation, no less) dropped in the middle of an otherwise pop-leaning sample and synth-oriented rap album. Wayne mixes a little bit of Jay-Z style self-aggrandization mixed with his own standard near-sensical tangent running ("My picture should be in the dictionary/Next to the definition of definition/Because repetiton is the father of learning/And son I know your barrell burnin' but/Please don't shoot me down") to great effect.

74. Lil Wayne "Get Out" (2004)

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73. Nelly Furtado f/ Lil Wayne "Maneater (Remix)" (2007)

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72. Lil Wayne f/ Rick Ross "John" (2011)

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Producer: Ayo The Producer
Album: Tha Carter IV
Label: Young Money, Cash Money, Universal Motown

Aside from the clear beat swagger jack (don't worry, we see you J.U.S.T.I.C.E. League), "John" has everything necessary to understand what goes on in Wayne's world. Within eight bars he's got a body count, practicing kama sutra, and putting Mother Earth on notice ("Top down, it's upset/Been fucking the world and nigga I ain't cum yet"). It's a scatterbrained stream of lyrical quips, but he makes it flow so fantastically.

71. Lil Wayne "3 Peat" (2008)

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Producer: Maestro
Album: Tha Carter III
Label: Cash Money, Universal Motown

As the opener to Carter III, "3 Peat" was an appropriately triumphant coronation for the Hollygrove spitter. On it Wayne urges listeners to swallow his words and taste his thoughts, and millions of listeners did just that. For many the aftertaste never left.

70. Lil Wayne And Juelz Santana "Rewind" (2007)

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69. Lil Wayne f/ 2 Chainz "Rich As Fuck" (2013)

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Producer: T-Minus, Nikhil S.

Album: I Am Not A Human Being II

Label: Young Money, Cash Money, Republic


The sexual musings and trite title may initially postulate a record with little to no value, but dig deeper and you'll discover "Rich As Fuck" is one of Lil Wayne's most recent gems. As the crisp, laid back production settles in, Weezy slyly indulges in exemplary one-liners with ease that play off his usual bravado ("These bitches think they're too fly, well tell 'em hoes I pluck feathers," "I keep a bad bitch, call me the BB King"). Match that with a more focused demeanor, and "Rich As Fuck" fittingly walks the line of commercial and lyrical without compromising quality.

68. Lil Wayne "Famous" (2006)

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67. Lil Wayne "Dr. Carter" (2008)

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Producer: Swizz Beatz

Album: Tha Carter III

Label: Cash Money, Universal Motown


For "Dr. Carter" Wayne put on his scrubs to perform a demonstration surgery on the rap game. He motivates aspiring emcees with inspiring words and Vicodin. He also kicks like a sensei and goes hard like geese erections. As an instructional guide, it's rambling and confusing at best-but as a learn-by-example display of rap madness, it's fascinating. It helps that Swizz Beats abandons his clunk and Casio chaos in favor of a perfectly simple David Axelrod loop in a transparent but fun attempt at true-school purism.

66. Cash Money Millionaires f/ Juvenile, Lil Wayne & Big Tymers "Project Bitch" (2000)

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Producer: Mannie Fresh

Album: Baller Blockin'

Label: Cash Money, Universal


One of more than a few Cash Money fronted odes to down-ass chicks, "Project Bitch" catches Baby, Mannie, Juve, and Wayne near the end of CMR's first reign. But they sound as fresh as they ever did. While the rest of the crew waste their breath on character traits, Wayne focuses solely on physical potential, as he was often prone to: "This is for the ones who wobble it and be puttin they mouth on it/They suck everything out of it then they catch it and swallow it."

65. Lil Wayne f/ Curren$y "Diamonds & Girls" (2007)

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64. Destiny's Child f/ Lil Wayne & T.I. "Soldier" (2004)

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Producer: Rich Harrison
Album: Destiny Fulfilled
Label: Columbia

To say that Destiny's Child were experiencing growing pains by their final album would be an understatement. "Soldier" found the usually clean-cut trio outing themselves as minor thug fetishists, and calling on T.I. and Wayne to bolster that cause. Wayne turns in an all-too-short verse but makes his mark, spinning the soldier analogy outward from an old B.G. hit: "See Cash money is an army/I'm walkin with purple hearts on me."

63. Lil Wayne "Money On My Mind" (2005)

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Producer: The Runners

Album: Tha Carter II

Label: Young Money, Cash Money, Universal


If the love of money is the root of all evil then Wayne must be the strongest branch on that tree. "Money On My Mind" boasts that money is all he can think of, but that encompasses a whole lot of territory in the bizarre brain of Wayne. So he unravels the money talk outward, penning letters to the toilet in which he explains the obvious ("Dear Mr. Toilet: I'm the shit"), outrunning the feds, and threatening to rape the marketplace.

62. Hot Boys "We On Fire" (1997)

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61. Lil Wayne "Pussy Monster" (2007)

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Producer: David Banner

Album: The Drought Is Over 2 (The Carter 3 Sessions)

Label: N/A


Despite a few very vocal adherents (Akineyle and The Beatnuts immediately come to mind), there was once a time when cunnilingus was something of a taboo in some corners of the hip-hop world. Or at least divisive. Too Short, for example, was unforgettably quick to scratch the name of any tender so bold as to demand reciprocation from his telephone book. (Yes, there was once a time when people still had telephone books, too.)

But, like with anything else, times and standards change. With "Pussy Monster" Wayne quite graphically explains why he'll be making no substitutions at the Vagina Diner. (The "pussy... pussy..." refrain seems to be a nod to Geto Boy Willie D's own pussyhound anthem, "I Some Need Pussy.")

60. Lil Wayne "Fuck Wit Me Now" (2000)

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59. Lil Wayne f/ Nutt Da Kid "Fuck A Nigga Thought" (2008)

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58. Juvenile f/ Lil Wayne & Turk "Hide Out Or Ride Out" (1997)

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Producer: Mannie Fresh

Album: Solja Rags

Label: Cash Money


There was always an elasticity to Cash Money-era Wayne. Not just in delivery but in his writing, which often ricocheted from one extreme to the next. This is especially evident on this album cut from Juve's Solja Rags. He turns the lights off, he turns the lights on. He unloads, he reloads. He unloads again. HIs proverbial target hides out or they ride out.

57. Lil Wayne "Pussy Money Weed" (2007)

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56. Lil Wayne "Tha Mobb" (2005)

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Producer: The Heatmakerz

Album: Tha Carter II

Label: Young Money, Cash Money, Universal


For an artist with such strong pop sensibilities, it's telling that Wayne still sounds most at home when just rhyming with no end in sight. On "Tha Mobb" Wayne is kicking his effortless flow forever. In fact he makes it seem so easy that when it's over you don't even realize that he just held your attention with no hook for five solid minutes and a whopping ninety or so bars.

55. Lil Wayne "Kush" (2007)

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Producer: Maestro

Album: The Leak

Label: Cash Money


A playful ode to the finer and greener things, "Kush" finds Wayne at his goofiest. "I got a grill/I don't have to get my tooth fixed/The tooth fairy would retire if I lose it." It's simply four minutes of steady bragging about how much he spent and smoked, but it works well. Word to his Gucc' boots.

54. Jadakiss f/ Lil Wayne "Death Wish" (2009)

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Producer: Alchemist

Album: The Last Kiss

Label: D-Block, Ruff Ryders, Roc-A-Fella, Def Jam


Wayne was a full-time pop star by the time "Death Wish" dropped, but you wouldn't have guessed it. This is pure, uncut murder music with Jada handing out his usual gravel-throated threats while Wayne spirals down syllables bringing his nine to life just long enough to end another's: "I'll put a barrel in Nina's head and let you reminisce."

53. Lil Wayne "Suffix (Dear Summer)" (2005)

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52. Lil Wayne f/ Curren$y "New Orleans Classic" (2006)

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51. Kanye West f/ Lil Wayne "See You In My Nightmares" (2008)

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Producer: Kanye West, No I.D.

Album: 808s & Heartbreak

Label: Roc-A-Fella, Def Jam


The masses are still split on Kanye's 808s & Heartbreak. Regardless, whether you think it's a brilliant departure or pure self-indulgence, it's hard to see Wayne as anything but a welcome addition to "See You In Nightmares." He perfectly anchors 'Ye's minimal synth mumbling with a more dramatic performance. And nobody amplifies an Auto-Tuned gurgle quite like Wayne does.

50. Drake f/ Lil Wayne "Ransom" (2008)

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49. Sqad Up "Grindin' Freestyle" (2002)

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48. Hot Boys "Clear Tha Set" (1999)

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47. Cam'ron f/ Lil Wayne "Touch It or Not" (2006)

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46. Lil Wayne "I'm Single" (2009)

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Producer: 40, Omen
Album: No Ceilings/I Am Not a Human Being
Label: Young Money, Cash Money

"I'm Single" is essentially Wayne making a Drake record. He calls on 40 for the droning synth beat and works in the same honest misogynist space that Drake occupies. But Wayne forces sympathy with such an awkward charm that you almost feel bad for the guy while he's so maliciously cheating on his girlfriend. Even at his most dramatic Drake has never been so convincing. It's proof that while the student may have become the teacher for the moment, the teacher is still the master.

45. Big Tymers f/ Lil Wayne & Juvenile "#1 Stunna" (2000)

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44. Drake f/ Lil Wayne "Miss Me" (2010)

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Producer: Boi-1da, 40
Album: Thank Me Later
Label: Young Money, Cash Money, Universal Motown


Drake couldn't make an album without his big brother and in-name-only CEO, so before heading upstate Wayne cut this verse for Drizzy's debut. His presence is more symbolic than anything else, but he does seem to be in good spirits on his playful verse. Bone Thugs sex joke? Check. Asthma/Weezy pun? Check. Sort of incomplete Drake-style implied/incomplete punchline about money and the film Groundhog Day that doesn't actually say anything about the movie, but we assume that's what he's talking about? Check. Whatever, it works

43. B.G. f/ Lil Wayne & Juvenile "Niggaz In Trouble" (1999)

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42. Lloyd f/ Lil Wayne "You" (2006)

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Producer: Big Reese
Album: Street Love
Label: The Inc., Sho'nuff, Universal Motown

Wayne lends a heartfelt verse to Lloyd for this Spandau Ballet-sampling hit. To this day it's not really clear as to why their song "True," has so much traction in urban music, but we aren't complaining. '80s Britain had its own sensitive thugs.

41. Lil Wayne "Fuck Tha World" (1999)

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Producer: Mannie Fresh

Album: Tha Block Is Hot

Label: Cash Money, Universal


Though shining and grinding were the primary themes on Tha Block Is Hot, he also got personal with "Fuck The World." It's the emotional centerpiece to the album, with Young Weezy fighting his demons and lamenting the still recent loss of his father figure, Rabbit. It's also the first time that he cursed on record.

40. Outkast f/ Lil Wayne & Snoop Dogg "Hollywood Divorce" (2006)

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Producer: Andre 3000
Album: Idlewild
Label: LaFace, Jive

Appearing in the middle of Outkast's derided and divided Idlewild album, "Hollywood Divorce" seemed a little like an attempted explanation for the increasing distance between the legendary duo. But it was Wayne who stole the show in the presence of the veterans.

He ran with the theme and turned in a somber critique of the media's continued exploitation of the black community and post-Katrina New Orleans in particular: "The hurricane came and took my Louisiana home/And all I got in return was a dern country song/This whole country's wrong."

39. Lil Wayne "Get Off The Corner" (2000)

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Producer: Mannie Fresh

Album: Lights Out

Label: Cash Money


Popular consensus will tell you that Wayne didn't hit his stride as a rapper until Tha Carter series. That it was a miraculous and sudden recovery from relative wackness. But popular consensus is wrong. "Get Off The Corner," the opening track from his sophomore outing was a conscious act of lyrical showboating and a strong outing from an emcee gradually coming into his own.

38. Lil Wayne "I'm Me" (2007)

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Producer: DJ Nasty & LVM

Album: The Leak

Label: Cash Money


"I'm me!" Obviously, you're you, Wayne. But this sort of self-affirmation seems to have played a big part in Wayne's rise to popularity. He seemed to be fueled by the logic that if you keep calling yourself The Best Rapper Alive, eventually it will come true. He did and it did.

If this rap thing doesn't take off for Wayne he just might have a bright future as a motivational speaker. Surely, Olympic swimmer, Michael Phelps, who listened to this song before each race on his way to winning eight gold medals, would agree.

37. Lil Wayne f/ Jay-Z "Mr. Carter" (2008)

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Producer: DJ Infamous, Drew Correa
Album: Tha Carter III
Label: Cash Money, Universal Motown

While Wayne and Jay previously occupied the same space on American Gangster's misplaced Beastie Boys homage "Hello Brooklyn 2.0," "Mr. Carter" feels more like a definitive statement from the two Carters. Jay's appearance is more symbolic than anything else. He came off a little too relaxed, if not rusty, to keep up with Wayne's three verses of verbal gymnastics. But it stands as a nice gesture of baton passing and a strong album track.

36. Hot Boys "Tuesday & Thursday" (1999)

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35. Juvenile f/ Lil Wayne "Run For It" (1998)

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Producer: Mannie Fresh

Album: 400 Degreez

Label: Cash Money, Universal


Wayne and Juve offer a couple dozen reasons for you to run when you see them coming. Wayne talks of jumping out of trees in camouflageand-and if the New Orleans rap canon is to be believed, this wasn't uncommon behavior. Jackers were known to hide in a tree, then jump out and rob unsuspecting bystanders of their Starter Jackets and such. Mannie's old rhyme partner, Gregory D (originally of the Ninja Crew, ironically enough), also addressed the subject on their proto-bounce club classic "Buck Jump Time."

34. Fat Joe f/ Lil Wayne "Make It Rain" (2006)

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Producer: Scott Storch
Album: Me, Myself & I
Label: Terror Squad, Imperial

So it turns out Wayne and Fat Joe really like having money, showing money, and throwing money. If you, the listener, lead a similar lifestyle, then this is your rain-making anthem for when "Make It Rain" is over.

For the rest of us broke folks it's a mere glimpse at the world of diamond and dollar dangling. Though Wayne only supplies the hook for the original mix, he kicks a meteorology-obsessed eight bars on the remix, which was also saturated by the likes of R. Kelly and Ricky Rozay.

33. Lil Wayne "BM J.R." (2004)

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Producer: Mannie Fresh, Batman

Album: Tha Carter

Label: Cash Money, Universal


Around the release of Tha Carter it was becoming obvious that Wayne was finally growing into the flow that he had always strove for. When this comfort level set in Wayne was clearly loving it, often styling like a monster just to show you he could. "BM J.R." is a perfect example of his "look Ma, no hands" show-off style...or "look Pa," maybe? Because Birdman's all over the track with some Diddy-style chest puffing.

He had good reason to be proud; you can almost hear Wayne scrunching up his face and attacking the mic: "I lie his body in grease set the fire to 'im/I tie his body in sheets put the tires to 'im/Make 'im feel the Escalade, put his feet in the blades/Damn! I'm the heat in the blaze."

32. Birdman f/ Lil Wayne "Pop Bottles" (2007)

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Producer: Steve Morales, Raymond "Sarom" Diaz
Album: 5 Star Stunna
Label: Cash Money, Universal

Expect nothing less than excess from a Baby and Wayne collab. Snatching its chorus from Jadakiss' "Get Ya Hands Up," "Pop Bottles" is a blur of nouveau riche imagery-hot tubs, Aston Martins, Marc Jacob goggles, and yes, bottle popping. Birdman and J.R. live the life of a good Pen & Pixel cover.

31. Lil Wayne "Get Em" (2006)

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Producer: Don Cannon

Album: Dedication 2

Label: N/A


Top to bottom, Dedication 2 was display of focus and drive, with Wayne just going in and spitting with a capital S. The tape's opener "Get Em" is a single extended verse and strikingly straightforward, doing away with the jokey space cadet business in favor of po-faced threats. He comes up for air just long enough for Drama to drop a short clip of The Impressions' "Keep On Pushin'" (get it?), and then he's right back at it with another 16 bars of madness.

30. Lil Wayne "Hustler Muzik" (2005)

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Producer: T-Mix, Batman
Album: Tha Carter II
Label: Cash Money, Young Money, Universal

Sure, Mannie and Wayne fit together like LEGO bricks, but one of the exciting things about Fresh's exodus was finally hearing Wayne work outside the camp with new producers and sounds on Tha Carter's second installment. For "Hustler Muzik," the very underrated T-Mix (formerly of the Suave House camp) slides Weezy a blues-tinged country rap tune, and he sounds right at home.

His warped sense of humor shines, too: "I ain't never killed nobody-promise." It sounds like a surprising confessional from the young hustler...but wait for it: "...And I promise if you try me he gon' have to rewind this track!" Only Wayne could so hilariously turn an admission of innocence into a threat of future guilt.

29. Hot Boys f/ Big Tymers "I Need A Hot Girl" (1999)

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Producer: Mannie Fresh
Album: Guerrilla Warfare
Label: Cash Money, Universal

With its goofy laid-back flows and plodding beat, most of "I Need A Hot Girl" feels more like a Big Tymers track than a Hot Boys one. That is, until Wayne and Turk hit the closing verse with a high-speed back and forth. With a madman's rasp Wayne makes a rundown of hot girl dance moves sound more like a street Kama Sutra: "She a donkey wit' it/She go wobbly then she know how to monkey wit' it/Open her legs and squeeze a nigga like she want me in it."

28. Lil Wayne "Upgrade" (2007)

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Producer: Swizz Beatz

Album: Da Drought 3

Label: Young Money


Though Beyonce might have the legal claim to Swizzy's beat for "Upgrade U," this Drought 3 freestyle makes it feel like it couldn't have been crafted for anybody but Wayne. He frantically shifts the timbre of his voice and makes his trademark lunatic genius style leaps of connectivity like comparing the synth horns to the Rocky Theme and then sending a rest in peace shout out to the late Apollo Creed. He also tells of having "just signed a chick named Nicki Mi-naj," who was then a relative unknown, and the boast feels both quaint and prophetic in light of her meteoric rise.

27. Lil Wayne f/ Reel "I Miss My Dawgs" (2004)

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Producer: Mannie Fresh, Raj Smoove

Album: Tha Carter

Label: Cash Money, Universal


For all his chest-puffing, Wayne has always seemed like a sentimentalist at heart. Take "Miss My Dawgs," a ballad in remembrance of all the ex-Hot Boys. Each member of the group gets a separate verse, with Wayne addressing B.G., Juve, and Turk in the first person. It really does feel like a dead homies number and not merely a homies-who-split-from-my-label one-and maybe there's some subtext to be taken from that. Either way, we're still patiently waiting on that Hot Boys reunion.

26. Sqad Up "Renegades" (2002)

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Producer: Eminem

Album: SQ4

Label: Sqad Up Entertainment


One of the crazy things about the SQ tapes was just how unstructured they were. Traditional songwriting was not a concern for the Sqad, so hooks and traditional 16-bar verses weren't necessary. More often than not, it just seemed like an exercise in which each member of the group would take turns rapping with great intensity for as long as possible until he ran out of either breath or bars, at which point the next emcee hopped on. Blessing Jay x Em's "Renegades" here, Nutt mans the mic for about a minute and then Wayne rides the rest of the track out for the remaining three.

25. Lil Wayne "Fireman" (2005)

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Producer: Doe Boys
Album: Tha Carter II
Label: Cash Money, Young Money, Universal

Dating back to his first single, Wayne's always had somewhat of a pyromaniac side. The themes of fire and heat might be the one unifying factor throughout his evolution. Heat stays on his mind, be it literal, sexual, biblical, a measure of popularity and skill, or the type that holds rounds. "Fireman" was him embracing these impulses, whispering about his wintertime allergies and walks with Satan. Don't burn yourself.

24. Hot Boys "Get It How U Live!!" (1997)

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Producer: Mannie Fresh

Album: Get It How U Live!!

Label: Cash Money


A 2008 Time Magazine profile of Wayne once embarrassingly dismissed the Hot boys as "'N*Sync with shivs." Sure, this puts a tidy bookend on the Wayne narrative-from shameless lowbrow pop star to respectable pop superstar-but it's a complete falsification. In reality, the Hot Boys project was more often a lyrical training ground for the roster, forgoing the poppier elements of other Cash Money releases in favor of straight spitting.

Usually it seemed like Wayne and Turk were apprenticing under or playing support to the more weathered Juvenile and B.G., but occasionally they stepped into the limelight. The title track from their debut is one such case, with Wayne rocking the lead-off verse and offering some very specific hustler mathematics.

23. Lil Wayne "We Come And See About It" (2007)

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Producer: Unknown

Album: The Drought Is Over 4

Label: N/A


"We Come See About It" is one of the dozens of loose leaks from the Carter III sessions, comped only on the unofficial The Drought Is Over 4 tape. There's a palpable urgency to the track; the beat builds tension as Wayne gets autobiographical-"Came in the game as a young'n..."-and then just drops you aggressively into his more street-minded rhymes.

22. Birdman f/ Drake & Lil Wayne "Money to Blow" (2009)

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Producer: Drumma Boy
Album: Pricele$$
Label: Cash Money, Universal Motown

Once a constant scene stealer, Wayne is becoming more comfortable in handing the reins to his successors as he ages. "Money To Blow" was purely a showcase for Cash Money's new golden boy Drake, who spits strange punchlines about Captain Hook and his car's roof that only sort of make sense.

Birdman's contribution is negligible and Wayne delivers a scant eight bars, but he says it best: "We gon' be all right if we put Drake on every hook." This is Baby and Weezy on the self-congratulatory tip, playing the background and letting their artist stack up the money for them. They've probably earned that luxury, though.

21. Hot Boys "Respect My Mind" (1999)

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Producer: Mannie Fresh

Album: Guerrilla Warfare

Label: Cash Money, Universal


Being the youngest Hot Boy, Wayne usually served as the crew's energy man. When he opened a song he not only drew ears in, but set the pace for the rest of the group. "Respect My Mind" finds him at his animated best, offering up deeply menacing threats of violence only to turn around and accent them with a cartoony, whistle-and-splat vocal effect.

20. Lil Wayne f/ Robin Thicke "Shooter" (2005)

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Producer: Robin Thicke

Album: Tha Carter II

Label: Cash Money, Young Money, Universal


Today it's hard to imagine a time when Wayne's radio presence was anything but ubiquitous, but in the "Shooter" era he was still chiding regionalist stations for being "rapper racist region haters." Of course, hearing Wayne over such accessible and bluesy, Gang Starr-inspired production-borrowed wholesale from Robin Thicke's "Oh Shooter-would be one of the first steps to converting those nonbelievers.

19. Lil Wayne f/ Cory Gunz "6 Foot 7 Foot" (2011)

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Producer: Bangladesh
Album: The Carter IV
Label: Young Money, Cash Money, Universal Republic

Similar to his 2008 single "A Milli" (with the exact same producer Bangladash), countless rappers hastily jumped on the instrumental of "6 Foot 7 Foot" but couldn't construct a record as monumental as Lil Wayne's. His energy was palpable, his delivery was relentless, and the rhymes were charismatically ferocious ("You know I'mma ball 'til they turn off the field lights/The fruits of my labor, I enjoy 'em while they still ripe").

This was all done over a zany Harry Belafonte sample which tipped the record into quintessential listening for Weezy fans. Standing 5'6'', Dwayne Carter reigned over his peers like a lyrical titan.

18. Lil Wayne "Something You Forgot" (2007)

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Producer: Unknown

Album: The Drought Is Over 2 (The Carter 3 Sessions)

Label: Young Money


The great thing about Wayne's intravenous line to the streets by way of the mixtapes is that it left no time for second guesses. Ideas that any budget-conscious A&R would squash actually materialize and hit the market before you can say the word "clearance."

Which brings us to one of the weirdest Wayne sample sources of all time-Heart's tacky 1985 mega-hit "What About Love?" Weirder still is how hard it actually sounds. Rather than aim for a Dipset-style tongue-in-cheek '80s beat, the uncredited producer just pushes Heart's inherent drama to the forefront with "Something You Forgot." Wayne does his part to turn up the tension with his vivid regrets over a lost love.

17. Birdman & Lil Wayne "You Ain't Know" (2006)

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Producer: Scott Storch

Album: Like Father, Like Son

Label: Cash Money, Universal


Before "Turn My Swag On," "You Ain't Know" was the early morning anthem. A hot torch on a Scott Storch (pause?), Wayne rolls out of bed with a nod to spirituality and Uptown pride, but is quite clear about putting money over everything. And though Birdman tends to get a flock of flak for his raps, his lumbering flow was a solid counterpoint to Wayne's spastic rasp throughout the very underrated Like Father, Like Son.

16. Lil Wayne f/ DJ Drama, Freeway, Willie the Kid, Detroit Red & Juice "Cannon (AMG Remix)" (2006)

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Producer: Don Cannon
Album: Dedication 2
Label: N/A

Don Cannon goes hard with the brand building as shouts of his name and bombastic horns carry Wayne's stream of consciousness from shootouts to kidnappings, with brief stop-offs for dry kush and to howl at the moon. "Cannon" is anthemic and almost feels too big for a mixtape. Its only real flaw lies in the preponderance of weed carriers clogging it up: While Freeway is always a welcome addition to any posse cut, the same can't be said for Detroit Red. Fortunately the rappers seem to appear in descending order of quality for maximum track skipping practicality.

15. Playaz Circle f/ Lil Wayne "Duffle Bag Boy" (2007)

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Producer: M16
Album: Supply Demand
Label: Disturbing tha Peace, Def Jam

A warning to potential Wayne collaboratiors: If you let him have the hook, he'll inevitably steal the whole song. Playaz Circle are competent rappers in their own right, but are completely overwhelmed by the sheer ferocity of Wayne's chorus on "Duffle Bag Boy." His voice is naked without Auto-Tune and he croons his heart out like that duffle bag was the last thing on earth he believed in. And if just a hook isn't enough for you then holler at the remiiix baaaby, where Wayne repopulates Tity Boi's opening flow with his own rhymes.

14. Lil Wayne "La La La" (2007)

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Producer: Infamous

Album: The Drought Is Over 2 (The Carter 3 Sessions)

Label: N/A


Not to be mistaken for the David Banner-produced "La La" that actually did make Tha Carter III, "La La La" is a bouncy outtake. It finds Wayne in rare form, tender and endearing while backed by a playful refrain of children. Its omission from the album seems strange in hindsight-with the right push it might have been his "Hard Knock Life" instead of just an underground classic.

13. Birdman & Lil Wayne "Leather So Soft" (2006)

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Producer: Jim Jonsin

Album: Like Father, Like Son

Label: Cash Money, Universal


The eskimos don't actually have a thousand words for snow, but Lil Wayne has at least that many ways to tell you how rich he is, in money and women. But what truly separates him from any number of rappers is his ability to inject those tropes with emotion.

"Leather So Soft" sounds somber from the jump, but it's not until the third verse that Wayne turns a song about convertibles and mistletoe dick kisses into something a little more personal: "I gotta die with money 'cause I wasn't born wit it/It was 9/27/82, baby due/Charity Hospital aka the city zoo."

12. Lil Wayne "Prostitute Flange" (2007)

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Producer: Maestro

Album: The Drought Is Over 2 (The Carter 3 Sessions)

Label: N/A


A rumored ode to Karrine "Superhead" Steffans, "Prostiute Flange" hears Wayne stumbling through a heavily Auto-Tuned and completely syrupy rendition of Musiq Soulchild's "You And Me." On paper it sounds like a mess but it's eerily effective, with Wayne compensating for his limits as a singer with raw emotions alone. (In recording, a flange is a chorusing effect somewhat similar to Autotune. In plumbing, it's "a rib or rim for strength, for guiding, or for attachment to another object.")

11. Juvenile f/ Mannie Fresh & Lil Wayne "Back That Azz Up" (1998)

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Producer: Mannie Fresh
Album: 400 Degreez
Label: Cash Money, Universal

As much as Wayne is a master of long-distance lyrical scatters, he's always been equally adept at doing a ton in a small space. He came very close to stealing the show on Juve's biggest hit with just one closing refrain: "After you back it up then stop, then drop drop drop drop drop it like it's hot."

It's an ideal bounce chant-simple in construction but unforgettable, especially when filtered through Weezy's gnarly rasp. The phrase was so strong, in fact, that Weezy would revisit it almost a decade later on his biggest hit, "Lollipop" and Snoop Dogg borrowed it to create the biggest hit of his career, "Drop It Like It's Hot."

10. Lil Wayne "Dough Is What I Got" (2007)

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Producer: Just Blaze

Album: Da Drought 3

Label: Young Money


Continuing in his long tradition of borrowing instrumentals from the other Mr. Carter, Weezy swiped Jay-Z's comeback-single-cum-Budweiser-commercial for "Dough Is What We Got." Wayne hit the track with twice the energy of Old Man Jay but remained deferent to his legacy saying, "I must be Lebron James if he's Jordan." He then reconsidered the analogy-"No, I want rings for my performance/I'm more Kobe Bryant of an artist."

9. B.G. f/ Lil Wayne, Juvenile, Turk & Mannie Fresh "Bling Bling" (1999)

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Producer: Mannie Fresh

Album: Chopper City in the Ghetto

Label: Cash Money, Universal


Rakim once boasted that he could take a phrase that's rarely heard and make it a daily word. Perhaps no act of rapping better illustrates this phenomenon than "Bling Bling." Wayne only provides the chorus, leaving the verses to his Hot Boy brethren, but he stole the show with only two words. Eleven years later the word "bling" is completely played out, the exclusive domain of ironic talk show hosts and soccer moms, but its resonance is undeniable. It's even earned an entry in the Merriam Webster Dictionary.

8. Lil Wayne "I Feel Like Dying" (2007)

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Producer: Jim Jonsin

Album: The Drought Is Over 2 (The Carter 3 Sessions)

Label: N/A


Though drug use might be responsible for some of Weezy's odder and sloppier late career decisions, it also brought out the best of him on some occasions. "I Feel Dying" is Wayne floating at a delightfully psychedelic pitch, diving into Codeine seas over Jonsin's ethereal beat.

The track never saw a proper release, but it still brought about a bevy of legal troubles, including a suit from South African songstress Karma-Ann Swanepoel, whose "Once" is sampled on the hook and a subsequent case in which Wayne's camp sued Jonsin for not properly revealing the sample.

7. Birdman & Lil Wayne "Stuntin' Like My Daddy" (2006)

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Producer: Jose Palacios
Album: Like Father, Like Son
Label: Cash Money, Universal

Forever father and son, Baby and Wayne have a complex relationship. One that the rest of the world might not ever truly understand. Let's just leave it at that and let them continue to make hits. "Stuntin' Like My Daddy" is just that and feels like a bit of a call back to the label's late-'90s days, complete with a tag team chorus and some throwback "Pwweenn on the Yahama" vocal effects courtesy of Weezy.

6. Lil Wayne f/ Juvenile & B.G. "Tha Block Is Hot" (1999)

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Producer: Mannie Fresh

Album: Tha Block Is Hot

Label: Cash Money, Universal


Riding Cash Money's hot streak, Wayne's debut solo single, "Tha Block Is Hot," was a giant step for the then-17-year-old. It introduced the world to Wayne as not just a tiny hypeman for Juvenile, but as a lively and entertaining standalone force. He splatters his still-tightening flow and cartoony vocal effects all over Mannie's impending track.

5. DJ Khaled f/ Akon, T.I., Rick Ross, Fat Joe, Birdman & Lil Wayne "We Takin' Over" (2006)

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Producer: Danja
Album: We the Best
Label: Terror Squad, Koch

With some very phoned-in appearances from T.I., Fat Joe and Rick Ross, "We Takin' Over" could very well have been yet another generic entry in what would eventually become an endless series of completely boring Khaled-helmed posse cuts...if it wasn't for Wayne.

After a brief but effective setup by Birdman, Weezy seizes control of the track for his unforgettable cleanup verse: "I am the beast/Feed me rappers or feed me beats/I'm untamed I need a leash /I'm insane I need a shrink."

And if that wasn't enough to claim the beat as his own, he revisited it on his Da Drought 3 tape with a sprawling new verse in which he handles the recently broken Birdman-kissing scandal in the swiftest way possible-with an admission: "Damn right I kissed my Daddy/I think they pissed at how rich my Daddy is."

4. Lil Wayne "The Sky is the Limit" (2007)

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Producer: Myke Diesel

Album: Da Drought 3

Label: Young Money


Wayne always had an unparalleled skill for claiming instrumentals as his own. On mixtapes he wasn't just rapping to beats or rewording hooks-he was building full songs. There might be no better example of this than "Sky Is The Limit," which swipes its beat from Mike Jones' slightly creepy would-be comeback single "Mr. Jones."

If you don't remember that song, you're not alone; nobody does. Mr. Jones himself probably can't even hum the hook today. But Wayne saw the potential in Myke Disel's track and restructured it into this bizarre and prideful anthem. He flies in the sky with fishes and swims in the ocean with pigeons. It's aspirational eccentricity. Also, when he was 5, his favorite movie was the Gremlins. That ain't got shit to do with this, but it was an interesting side note worth mentioning.

3. Lil Wayne f/ Static Major "Lollipop" (2008)

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Producer: Deezle, Jim Jonsin
Album: Tha Carter III
Label: Cash Money, Universal Motown

Love it or hate it, "Lollipop" is Wayne fully unhinged, yet somehow able to fit into a pop song formula. It's one of the strangest and most abrasive ballads to ever hit the airwaves, with all empty space and drug addled Auto-Tune mumbles. That it's Wayne's biggest hit is an oddly appropriate contradiction.

Here is a scrappy troll of a gangsta rapper turned into a sex icon, singing passionately with a singing voice that would be atrocious had it landed in anyone else's body. But he sells it on presence and persona. And, yes, today you aren't going to ride around with your homies listening to "Lollipop," not just for any implications but because the song is dangerously played out.

So consider instead the very slept-on remix, which keeps the beat and the Auto-Tunage, but runs three strong verses of actual rapping through it all. Kanye makes a big show about how he's not going to let Wayne murder him on this track. 'Ye sounds great, playing the scrappy underdog position where he's most comfortable, but none of that stops Wayne from still basically murdering him with the verses that follow.

2. Lil Wayne "Go D.J." (2004)

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Producer: Mannie Fresh
Album: Tha Carter
Label: Cash Money, Universal

Despite what the revisionists might tell you, the main distinction between early Wayne and later Wayne was less about lyrics than it was delivery and construction. In his Hot Boy days, Wayne's flow was playfully loose and sometimes sloppy. "Go DJ" is a testament to his refinement: tightly constructed, with deep internal rhymes and every syllable in its perfect place: "I fly by you in a foreign whip on the throttle/With a model bony bitch/Pair of phony tits."

Meanwhile Mannie plays the perfect hypeman, shouting out grown ups, in between, chirren, and babies. (The "Go DJ" hook is lifted from old guard Cash Money members UNLV's local hit of the same name. Their subsequent disses never garnered a formal response, but Wayne quietly added insult to injury by boosting their original "Go DJ" beat for Dedication 2's "Walk It Off." Leaving behind just residue and bone, indeed.)

1. Lil Wayne "A Milli" (2008)

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Producer: Bangladesh
Album: Tha Carter III
Label: Cash Money, Universal Motown

Given the climate of anticipation surrounding it, the success of Tha Carter III was inevitable. Any lead single would've hit radio with a bang. But rather than play it safe with the pop cash, Wayne used "A Milli" to both lock down his core fanbase and convert quite a few outsiders. To Bangladesh's plate-shifting bass tones he rapped like a demon possessed, a goblin in a sea of mere goons.

It's a truly singular pop record and it might just be radio's last rap-centric hit. Which is to say that the actual act of rapping, not a catchy hook or a melodic beat, was its primary draw. (After all, the hook barely exists-it's just a fragment of a couple Phife syllables snatched from an obscure A Tribe Called Quest remix.) "A Milli" was Wayne's coronation, the moment where the hip-hop nation (vocal minority of hating ass curmudgeons aside) had no choice, but unite in collective awe of the kid from Hollygrove.

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