The 50 Best Philadelphia Rap Songs

All the way live, from the 215. A thorough look at Philly's greatest contributions to hip-hop.

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It's difficult to put a finger on the Philadelphia hip-hop scene. It's been over 30 years since radio personality Lady B started it all, and despite decades of success, the scene still seems to share that figurative chip that the entire city has on its shoulder. Philly hip-hop has always been respected, but doesn't always receive the credit that it deserves.

The truth is, Philly has been representing since hip-hop's earliest days, and was crucial in some of the genre's most pivotal moments. Schoolly D exposed the world to gangsta rap. DJ Jazzy Jeff & the Fresh Prince took hip-hop to the Grammys. Lawrence "L.G." Goodman founded the city's first rap record label, Pop Art Records, acting as the city's Godfather of hip-hop. He was an essential figure in establishing hip-hop's entrepreneurial spirit.

The '90s saw the emergence of The Roots, who became one of hip-hop's most adored groups without massive commercial success. With over two decades of experience and a catalog the length of Broad Street, their legacy is cemented. Jay-Z's Roc-A-Fella reigned supreme in Philly thanks to the efforts of Beanie Sigel, Freeway, and their State Property collective. Eve became the First Lady of Ruff Ryders, following in Lady B's footsteps and eventually branching out into acting.

Next up is Meek Mill, who has evolved from his battle rap roots and overcome setbacks (like prison time) to release his debut Dreams & Nightmares this week. During what's surely another proud moment for the city's hip-hop scene, Complex reminisces on the 50 Best Philadelphia Rap Songs. Even if you've never been to a Motor Inn party or a Sonny Hill League game, don't know what a Sunni is and never owned a pair of the "salt and pepper" GUESS Jeans with the pen pocket, you'll still be able to appreciate these timeless tracks.

Written by Julian Kimble (@JRK316)

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50. Peedi Crakk f/ Freeway, Young Chris & Beanie Sigel "One for Peedi Crakk" (2002)

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49. Three Times Dope "Funky Dividends" (1989)

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Album: Original Stylin'

Producer: Chuck Nice

Label: Arista



"Funky Dividends" has E.S.T lamenting about dealing with a girl who constantly has her hand out. The frustration of dealing with a gold digger will even make dudes with the deepest pockets re-evaluate their relationship. Michelle, the girl that E.S.T is stressing over, even goes as low as to talk about what other dudes bought her, and question his status as the "Greatest Man Alive." The nerve. There's no country for bratty girls, so best believe she gets the boot. By telling the story of a real-life dilemma, 3xD spoke to and for a generation of guys fed up with dealing with delusional princesses. The song would later be sampled by Diddy for a re-working of Total's "Kissing You."

48. Dutch & Spade f/ Beanie Sigel "Dead Man Walking" (1999)

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Album: The Tunnel

Producer: Darrell "Digga" Branch

Label: Def Jam



Dutch & Spade were a fraction of Major Figgas, and at the end of the '90s, the duo hooked up with Beans for the hard-as-nails "Dead Man Walking." "You think Philly cats won't snap on your muthafucking ass?" Dutch asks during the song's intro, and MF's other comedian got serious on this track, reminding listeners just how unfriendly the streets can be for those who get friendly with police. You get no love from Dutch, Spade-O, or the Broad Street Bully if you rub elbows with the Feds.

47. The Roots f/ DJ Jazzy Jeff & Jazzyfatnastees "The Next Movement" (1999)

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Album: Things Fall Apart

Producer: The Grand Wizzards

Label: MCA



"The Next Movement" is a great exercise of the supremely confident, braggadocios lyrics that make Black Thought one of the best MCs in the game. "I tilt my crown, then blow down a diamond kiss/You need to buy a CD and stop rewinding this/I'm the finalist, shining like a rugged amethyst/And at your music conference, I'm the panelist/Listen close to my poetry, I examine this/Like an analyst, to see if you can handle this."

Thought raps in that matter-of-fact, "I-just-rap-better-than-you" tone. Additional background vocals from the Jazzyfatnastees and scratches by DJ Jazzy Jeff are the perfect accents to an already near-perfect song.

46. Pretty Ugly "Stack Gz Regardless" (2001)

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Album: N/A

Producer: Ric Riggler

Label: Game Recordings

"It's Pretty Ugly, I should've been on" announces the rapper with the clever name, just before reminding rappers that his arrival signals their demise and telling Lil Kim—circa 2001—that he wants her to have his seed. It's that confidence and that thick Philly accent that allowed Pretty Ugly to create a track that flew under the radar to most, but was extremely important to others. Maybe the self-proclaimed Bigfoot of hip-hop is more effective as Philly's best kept secret.

45. The Goats "Do the Digs Dug" (1992)

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44. Konfidential "How We Roll" (2002)

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43. Three Times Dope "Greatest Man Alive" (1989)

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42. Gillie Da Kid "Something to Bounce To" (1999)

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41. Da Fat Cat Clique "Da Flow" (1996)

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40. Schoolly D "Gangster Boogie" (1984)

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39. Bahamadia "Uknowhowwedu" (1996)

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Album: Kollage

Producer: Ski, DJ Redhanded

Label: Chrysalis, EMI Records



As a member of the Gang Starr Foundation, Bahamadia got a huge cosign prior to dropping her debut album. Over spacey, mid-90s boardwork by Ski, she paid homage to the Philly hip-hop scene in her trademark monotone. "Uknowhowwedu" came out during a period when even the female MCs who sold sex could rap, but Bahamadia was 100% skill and no gimmicks. It's that respect for lyricism and her effort to quietly put Philly on the map that made this track so important.

38. Cassidy "My Drink N My 2 Step" (2007)

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Album: B.A.R.S. The Barry Adrian Reese Story

Producer: Swizz Beats

Label: J Records, Full Surface, Ruff Ryders



Following the success of his second album, Cassidy fell on dark days. After being released from prison following a charge for involuntary manslaughter and nearly losing his life in a car accident, he bounced back with the Doug E. Fresh-sampled "My Drink N My 2 Step." With a hook and a beat from Swizz, this ode to the simple, yet wonderful things proved Cassidy could put his issues behind him and deliver hits.

37. Da Youngstas "Hip Hop Ride" (1994)

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Album: No Mercy

Producer: Marley Marl

Label: Atlantic



"Hip Hop Ride" was Da Youngstas' biggest hit, and the summery tribute to the culture that helped raise them is a testament to their pedigree. The trio are the sons and nephew of Lawrence "L.G." Goodman, the founder of Pop Art Records—Philly's first hip-hop record label. The song has the young MCs shouting out all of their favorite rappers. Though undeniably Philly, "Hip Hop Ride" has a West Coast swing that will make you want to roll your windows down and hit up a pool party decked out in a Jason Kidd jersey from his first stint with the Mavs.

36. State Property "Want Me Back" (2003)

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35. The Roots f/ Musiq "Break You Off" (2002)

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Album: Phrenology

Producer: Kamal Gray

Label: MCA, Geffen



"Break You Off" is hands down The Roots' most seductive song. 2 Chainz can rap about fucking other dudes' girlfriends all day long with hilarious vigor, but here, Black Thought does it with a unique charm and maturity. This is what adultery sounds like on wax. From Thought's mentions of doing "the freakiest things you've done in your life" to referencing blaxploitation flicks and likening his co-conspirator's frame to Pam Grier in the '70s, it's brilliant.

34. Philly's Most Wanted "Cross The Border" (2000)

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Album: Get Down or Lay Down

Producer: The Neptunes

Label: Atlantic



How quickly people forget that the first duo The Neptunes helped attain success was Philly's Most Wanted. "Cross the Border" wasn't their first song, but it was the lead single from their appropriately Philly titled debut, Get Down or Lay Down.

Complete with that infamous Spanish guitar heard in so many Neptunes beats, "Cross the Border" has Boo and Mr. Man searching for that ride or die chick willing to put it all on the line in the name of love and the drug game. It became one of Most Wanted's most popular singles and it's so good that it makes the misspelling of "Cancun" forgivable. How did the engineer let that slide?

33. Young Gunz f/ Rell "No Better Love" (2003)

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Album: Tough Luv

Producer: Chad Hamilton

Label: Roc-A-Fella, Def Jam



"I think I might wife her/You know, powder blue Roc-A-Wear suit, white Nike her." Though Jay-Z's appropriation of Young Chris' flow has been much documented, it was the youngster's use of this Hov line that set the tone for the Young Gunz 2003 hit. Over a smooth Luther Vandross sample handled masterfully by Chad Hamilton, Chris and Neef took the time to spit something special for the ladies.

The duo really shines on the song's last verse, as they go back and forth, trading verses and showing the chemistry that made their 2004 debut Tough Luv so promising. The Roc truly ran things in Philly for nearly a decade, and what's more Roc-A-Fella then having Rell himself croon on the hook? That's golden.

32. Beanie Sigel "What Ya Life Like" (2000)

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Album: The Truth

Producer: Robert 'Shim' Kirkland

Label: Roc-A-Fella, Def Jam



Beanie Sigel has been known to beat his listeners down (figuratively), and one of the worst beatdowns comes in the form of "What Ya Life Like." Think you got it bad? Listen to Beans paint the perfect picture of incarceration and what it really means to be stripped of your freedom, dignity, and humanity. Listen to him explain the realities of prison and you'll feel like you're right there in the hole with him. Listen to how low his voice gets when he says "no parole," how he described abuse from guards and the extremes some go to in order to continue that illegal life, even while incarcerated. This ain't Oz, this is real life. What's yours about?

31. DJ Jazzy Jeff & The Fresh Prince "Brand New Funk" (1988)

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Album: He's the DJ, I'm the Rapper

Producer: Bryan "Chuck" New, DJ Jazzy Jeff & The Fresh Prince, Pete Q. Harris

Label: Jive, RCA



Believe it or not, there was a time when people couldn't easily identify Will Smith. He and his partner Jeff Townes decided to title their second album He's the DJ, I'm the Rapper so people knew who was who. "Brand New Funk" was the album's first single, and though it failed to find commercial success, it stands as a gem. Thanks to the up-tempo beat, Jazzy Jeff's turntablism, and the Fresh Prince's rapid-fire delivery, the song is lyrical cardio. Nearly 20 years after its release, Jazzy Jeff recruited Peedi Crakk for a special edition of the track titled "Brand New Funk 2k7."

30. Da Youngstas "Crewz Pop" (1993)

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Album: The Aftermath

Producer: 118th Street Productions

Label: East West, Atlantic



After being overshadowed by Kris Kross, Da Youngstas went for a more aggressive sound on their second effort, and "Crewz Pop" is the perfect example of that. Their youth didn't stop them from creating a Carhartt rap masterpiece, all with the help of Treach himself.

29. Young Gunz "Can't Stop, Won't Stop" (2003)

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28. Eve f/ Faith Evans "Love Is Blind" (1999)

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Album: Let There Be Eve...Ruff Ryders' First Lady

Producer: Swizz Beats

Label: Ruff Ryders, Interscope



Eve asserted herself as a role model with her first album, not just because she was the first female rapper to have her album debut at No. 1, but because she addressed the subject of domestic violence. Flanked by Faith Evans, Eve uses "Love Is Blind" to tell the story of an abusive relationship from the perspective of a concerned friend. Although it's a warning for young women, it's real (and good) enough for anyone to feel it.

27. Meek Mill f/ Young Chris "House Party" (2011)

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Album: Dreamchasers

Producer: Tone Beats (The Beat Bully)

Label: MMG, Warner Bros.



This came out of nowhere last summer, but from the time Meek Mill (extra loudly) announced himself on the track, you knew that "House Party" was more than just spaghetti that stuck to the wall. The sheer idea of a house party is something everyone loves, but the third track from the first Dreamchasers mixtape was a special occasion. "House Party" is Meek at his best, going off in high-pitched, rapid fire fashion over The Beat Bully's production. With the help of Young Chris, this mixtape track ended up being one of 2011's biggest songs.

26. R.A.M. Squad "Unfortunate" (1996)

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Album: Operation Lock The City

Producer: Boy Back, Tommy Hill

Label: Echo International



Coming out of North Philly's infamous Richard Allen projects, R.A.M. Squad emerged during the mid-90s on the back of this hood anthem. Old school parties and lunch time mixes are incomplete without this classic from the Richard Allen Mob, who saw moderate success during the late '90s and into the millennium. The group eventually dissolved after legal troubles because they weren't just rapping about the life back in the day—they were living it. Sadly, member Tommy Hill was killed last December during a robbery in East Mount Airy.

25. Beanie Sigel "Feel It In the Air" (2005)

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Album: The B. Coming

Producer: Heavy D

Label: Dame Dash Music Group, Def Jam



After a few side endeavors and some trouble with the law, Sigel bounced back nicely with The B. Coming. Released after the fall of the the Roc-A-Fella dynasty, the album's tone is heavy with isolation, bitterness, and despair.

One of its many standout tracks was the skeptical, Heavy D-produced "Feel It In the Air." Here, Beans issues a cautionary tale that's soaked in paranoia and regret. When he says his spider senses are tingling, you know, just like he does, that something bad is coming. "Your handshake ain't matching your smile" is motivation to never give a weak dap, and advice to scrutinize everyone you think is suspect.

The timing of the song's release was ironic. Not only did it coincide with the demise of The Roc as we knew it at the time, it also dropped as The Wire's third season came to a close. Both this song and Season 3 of The Wire are, in some capacity, about inevitable betrayal. As Beans reminds us, "It ain't an us, or we, or I'ma thing/It's a good, bad karma thing." But it's mostly bad and he knows it.

24. Schoolly D "Saturday Night" (1986)

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Album: Saturday Night! – The Album

Producer: Schoolly D

Label: Schoolly D Records, Rhythm King Records, Jive



Schoolly D's second album, Saturday Night! – The Album, is best known for the track "Saturday Night." Using the break for Melvin Bliss's "Synthetic Substitution" and that unmistakably funky swing of "Soul, Soul, Soul" by The Wild Magnolias, Schoolly D weaves the tale of the typical Saturday night in the life of a young man. All of the key ingredients—liquor, drugs and sex—make appearances, and Schoolly even gets caught having sex by his mother.

"Saturday Night" isn't all party and bullshit however, as there's a message in the final verse. Fueled by weed, wine, and coke, Peter the Pimp ends up getting popped by the police while sticking up a bar. He finds himself standing in front of a judge with a sense of humor, who encourages him to stick to beer and reminds him that he'll be property of the state of Pennsylvania for the next 20 years. The song was sampled by The Roots on Things Fall Apart's "Without a Doubt" and appeared in Abel Ferrara's crime drama King of New York.

23. Tracey Lee f/ Notorious B.I.G "Keep Your Hands High" (1997)

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22. Philly's Most Wanted "Please Don't Mind" (2001)

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Album: Get Down or Lay Down

Producer: The Neptunes

Label: Atlantic



The Neptunes ran shit during the Aughts, and they shared some of their best production with a pair of duo's—one from VA, and the other from PA. Most Wanted dropped their debut album, Get Down or Lay Down in August of 2001, which is best remembered for the Pharrell and Chad orchestrated "Please Don't Mind." Over the signature combination of Spanish guitars and random, spaced-out sounds, Boo and Mr. Man spit occasionally hilarious and disrespectful lines in poem-like fashion.

When a song opens with "Excuse me bitch, what's your name?" a very distinct tone is established. When there are references to hitting more bitches than Ike Turner (sexually) and guns that'll make James Brown lose his soul, you're captivated. Women have fallen for lamer pick-up lines, and the Neptunes production is the perfect sonic landscape for Boo and Mr.'s arrogant approach.

21. Jakk Frost "Philly Love" (2002)

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Album: U Don't Know Jakk

Producer: 100milez

Label: Face Off Ent.



About a decade ago, Jakk Frost inadvertently created a lyrical Philadelphia history lesson with the anthem "Philly Love." The beauty of this song is that it's like an inside joke—you only truly understand its power if you're from the city. Even if you're too young to remember when weed used to come in brown envelopes, you have no choice but to feel it when Frost mentions everything from The Spectrum to Lady B to the Junior Black Mafia. He even finds time to mention the legendary Philly thug Aaron Jones, pill popping, the infamous lean corner of 17th & Jefferson, City Blue as a fashion staple, and the fact that Lawrence Goodman (father and uncle to Da Youngstas) started Philly's first rap label.

He includes everything from Charlie Mack celebrity basketball games to Wilt Chamberlain to Rasheed Wallace and legendary Temple University basketball coach John Chaney. Oh, and of course Allen Iverson, who isn't from Philly but will always be an adopted son.

The feeling a Philadelphia native gets when listening to this song is the equivalent to when the 76ers won the first game of the 2001 NBA Finals. It's on par with when the Eagles went to the Super Bowl after the 2004 season. And it's the same euphoria that was felt after the Phillies won the 2008 World Series. Go ahead and look up that clip of AI stepping over Tyronn Lue, because it's that real.

20. Major Figgas "Yeah That's Us" (2000)

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Album: Figgas 4 Life

Producer: Darnell Marshall, Dean Murder, Hotrunner

Label: Ruff Nation/Warner Bros.



Long before Ab-Liva was part of The Re-Up Gang, he was part of Major Figgas. Erie Avenue's finest was a deep crew, and their lone album produced this hit which reached No. 30 on the Hot R&B/Hip-Hop Singles and No. 2 on the Hot Rap Singles charts. Drenched in references to designer clothes, the lavish life, and the goon shit you're accustomed to from Philly rappers, "Yeah That's Us" was certified Walnut Street lounge rap.

In addition to the 6'9" Don, the track featured Spade, who jumped things off. Liva Don introduced himself as the "Smooth thug with the good hair" before the one-and-only Gillie Da Kid wrapped things up. Long before Gillie striking viral gold with his roasts of Cassidy and Lil Wayne, he was telling listeners "that ain't what the whores like." It's that charm that's kept him relevant to the scene for years after, and even led to a guest spot on the short-lived Starz drama Gravity.

19. Lady B "To the Beat Y'all" (1979)

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18. MC Breeze "Discombobulatorbubalator" (1985) / MC Breeze "It Ain't New York" (1985)

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17. High & Mighty f/ Mos Def & Skillz "B-Boy Document '99" (1999)

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Album: Soundbombing ll

Producer: DJ Mighty Mi

Label: Rawkus Records



High & Mighty—composed of DJ Mighty Mi and Mr. Eon—struck underground gold with "B-Boy Document '99," the sequel to "B-Boy Document." This fast-paced cut appeared on their 1999 album, Home Field Advantage, and the celebrated Rawkus compilation Soundbombing ll.

The duo got some help from Mos Def, whose vicious opening verse was laced with battle-ready rhymes that praised independence and denounced artists whoring themselves out for record labels. It was the perfect alley-oop for Skillz (then Mad Skillz) and Mr. Eon, who got a chance to deliver one of his much-loved sports references during the last verse: "Defeating me is like Latrell choking up John Thompson."

The song became something of a cult hit, finding it's way onto the soundtrack of Tony Hawk's Pro Skater 2, and more famously on the very first And 1 mixtape.

16. Cassidy "I'ma Hustla" (2005)

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Album: I'ma Hustla

Producer: Swizz Beats

Label: J Records, Full Surface, Ruff Ryders



Philly is a blue collar city, so it would've been hard for Cassidy's grind-time anthem to fall on deaf ears locally. Not even Barry Reese himself could anticipate that this song would blow up like it did and make him the first rapper to have a platinum ring tone. Cassidy's aggressive, battle-style rhymes fit perfectly over that "Dirt Off Your Shoulder" sample. This is one of the songs that made Swizz Beats a bankable producer again and proved that Cassidy was here to stay.

15. Schoolly D "Gucci Time" (1985)

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14. State Property "Roc The Mic" (2002)

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Album: State Property OST

Producer: Just Blaze

Label: Roc-A-Fella, Def Jam



With a hook that pretty much demands that you recite it, this Dame Dash dance-ready hit was the lead single from the State Property soundtrack, and hit No. 55 on the US Billboard Hot 100 in 2002. As one of Just Blaze's earliest masterpieces, it features Freeway's sing-songy flow and Beans' trademark verbal uppercuts. Beans was established by this point, so it was an opportunity to introduce to the world Freeway and his off-beat rhyme style. It worked.

13. DJ Jazzy Jeff & The Fresh Prince "Parents Just Don't Understand" (1988)

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Album: He's the DJ, I'm the Rapper

Producer: DJ Jazzy Jeff

Label: Jive, RCA



"Brand New Funk" never became the mainstream hit that it should've been, but DJ Jazzy Jeff & The Fresh Prince finally struck gold with the album's follow-up single, "Parents Just Don't Understand." Over wonderfully '80s hip-hop production, Smith reveals the plight of the teenager in the form of struggle raps. From references to embarrassing shopping excursions to The Gallery to the doomed borrowing of his parents' car, this song is everything that '80s teen movies were made of. The song was also the first to win a Grammy for Best Rap Performance, and was even referenced on The Fresh Prince of Bel-Air, thus adding to its legend.

12. Steady B f/ KRS-ONE "Serious (Ceereus BDP Remix)" (1988)

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11. Freeway f/ Peedi Crakk "Flipside" (2003)

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Album: Philadelphia Freeway

Producer: Just Blaze

Label: Roc-A-Fella, Def Jam



Start a conversation about a song that changes your mood when you hear it, and you're probably talking about "Flipside." Anytime a song begins with "WOOOOOOOO!" you're in for a good time, and Freeway's Peedi Crakk-assisted party-starter might have been the party song of the year in 2003. Backed by Just Blaze's bombastic production, Freeway is wonderfully all over the place with his up and down flow, and Peedi Crakk anointed himself the "Prince of SP" after delivering his signature "Rrrrring!"

This is a feel good track that still gets parties going, and will turn weddings up for generations. The video, which features Beanie Sigel threatening to beat people up as usual, is also the closest that Peedi will ever be in proximity to Jay-Z again.

10. Tracey Lee "The Theme (It's Party Time)" (1997)

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9. The Roots f/ Erykah Badu & Eve "You Got Me" (1999)

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Album: Things Fall Apart

Producer: The Grand Wizzards

Label: MCA



If you haven't noticed by now, The Roots like to name their albums after books. Their fourth LP, Things Fall Apart, borrows the name of Chinua Achebe's classic 1958 novel and "You Got Me" was the breakthrough song from what is widely recognized as The Roots' breakthrough album.

The song was co-written by a then-unknown Jill Scott, who originally sung the song's chorus and bridge. She was replaced by the established Erykah Badu, whose reassurance on the hook that she has her man's back, no matter what, is unquestioned. Black Thought and Eve (then known as Eve of Destruction) spin the story of a relationship that has tested the MC's devotion to his craft and the shadow of doubt that friends can cast on lovers.

Both agree that "sometimes, relationships get ill," but we all know behind every great man is a great woman who held him down.

8. Cool C "Glamorous Life" (1989)

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Album: I Gotta Habit

Producer: Steady B, Lawrence Goodman

Label: Atlantic



By taking a shot at the Juice Crew with his first single, it was obvious that Cool C was out to make a name for himself. As one of the OG members of The Hilltop Hustlers, Cool C dropped his debut album in 1989. The album's breakthrough single, "Glamorous Life," flipped Lyn Collins and Bobby Byrd samples as Cool C rapped about the finer things in life. He name-drops Gucci, Louis Vuitton, and the '80s staple MCM, and his mention of Alpinas will make you want to wash your 5.0 and hit a house a party, just for old time's sake.

Unfortunately, things aren't so glamorous for Cool C these days, as he sits on death row after the 1996 murder of a Philadelphia police officer following a botched bank robbery.

7. Eve f/ Gwen Stefani "Let Me Blow Ya Mind" (2001)

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Album: Scorpion

Producer: Dr. Dre, Scott Storch

Label: Ruff Ryders, Interscope



Lightning struck twice for Eve on her second album when she hooked up with Gwen Stefani for the brilliance that is "Let Me Blow Ya Mind." This wonderfully groovy track, produced by Dr. Dre and Scott Storch, was a smash hit in the United States and became Eve's second consecutive single to blow up in the United Kingdom. It will forever hold a place in history, as it was the first song to win a Grammy for Best Rap/Sung Collaboration.

6. Beanie Sigel "The Truth" (2000)

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Album: The Truth

Producer: Kanye West

Label: Roc-A-Fella, Def Jam



Regardless of what Beans says about Kanye these days, he knows that 'Ye blessed him with a lot of heat early in his career. Over a sample of "Chicago" by Graham Nash, Sigel set the tone for his first album and career with "The Truth." Every bar is like a bully poking you in the chest with his index finger, insulting you with brutal honesty. It's that rhyme style, the "arsenic flow" and the fact that he still lives every bit of what he's talking about that really made Beanie Sigel the Broad Street Bully.

5. Meek Mill "Ima Boss" (2011)

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Album: Self Made Vol. 1

Producer: Jahlil Beats

Label: MMG, Warner Bros.



Though everyone following the Philadelphia rap scene knew about Meek Mill before he inked a deal with MMG, Self Made Vol.1 was his chance to grip listeners up, shake them violently, and scream at them. No song on the compilation album captures its true essence more than "I'm a Boss." With the help of the Bawse, Meek detailed why he was already a young boss well on his way to years of success. It's him at his finest—screaming over a Jahlil Beats track. It's also inspirational enough to make even those who would never, ever hop on a bike pop wheelies.

4. Freeway f/ Jay-Z & Beanie Sigel "What We Do" (2002)

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Album: Philadelphia Freeway

Producer: Just Blaze

Label: Roc-A-Fella, Def Jam



With "What We Do," Freeway established himself as a rapper who had to be taken seriously. He showed flashes on "1-900-Hustler," but it was this track from his debut that showcased the passion of his rhymes. With his State Property boss and the boss featured on the track, Freeway brought his A-game, breaking down the mindset of those who resort to a life of crime because it's their only option for survival. It's exactly what Jay-Z was talking about at the beginning of "Can I Live?" when he says drug dealers hustle out of a "sense of hopelessness." With this up-tempo Stick Up Kid anthem, Freeway had the entire nation saying, "I ain't talking bout chicken and gravy mang!" and meaning it.

At Jay-Z's urging, Freeway kicks his verse into overdrive, and you don't have to be from the hood to feel his pain. All the while, Just Blaze's plodding production beats like the heart of a would-be robber who recognizes the error of his ways but sees no other way out. From Freeway's blackout first verse, to Jay-Z's assertion that no witnesses survive due to the presence of Free's incriminating Sunni, to Beans' frustration at grinding from the bottom just to make it to the bottom, this is easily one of the best rap songs to ever come out of Philadelphia. You do the math.

3. The Roots f/ Raphael Saadiq "What They Do" (1996)

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Album: Illadelph Halflife

Producer: Questlove, Grand Negaz, Raphael Saadiq

Label: DGC, Geffen, MC



Black Thought says that he wants it made like Special Ed on the song's final verse, but wasn't about to jump through hoops to get there. "What They Do" eviscerates the record industry, lampooning the here today, gone tomorrow artists who were in it for the money and not the love. On the hook, Raphael Saadiq warns to "never do, what they do," while Black Thought laughs at the rappers who sell out to make it.

The song's video, directed by Philly native Charles Stone lll, is one of hip-hop's best satires ever. It clowns all of the stereotypes that came along with hip-hop music videos during that period in a subtle, yet effective manner. The song wasn't a dart at anyone in particular, but anyone that was bothered by it was probably being visited by their guilty conscience.

2. DJ Jazzy Jeff & The Fresh Prince "Summertime" (1991)

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Album: Homebase

Producer: Hula & K. Fingers

Label: Jive



Long before Will Smith was Mr. Fucking Blockbuster, he was The Fresh Prince. The lead single from his and DJ Jazzy Jeff's fourth album Homebase, "Summertime" has become a timeless pop culture phenomenon, with popularity spanning over two decades. Part of its brilliance is that you don't have to be a Philly native to appreciate it. Even if you've never been to a barbecue at Belmont Plateau, you've more than likely been to one somewhere similar during the summer months and experienced everything that Smith describes.

Over a sample of Kool & The Gang's "Summer Madness," Smith offered imagery so vivid that it extended beyond the city and became synonymous with summer. The song won a Grammy for Best Rap Performance by a Duo or Group and still works its way into rotation as the season changes for the better each year.

Although they've both become icons, neither Smith nor Jazzy Jeff have forgotten the song that catapulted them to stardom. Jazzy Jeff has released a Summertime mixtape with Mick Boogie the past three summers, and Smith performed the intro—an updated version of "Summertime"—on the latest installment.

1. Schoolly D "P.S.K. What Does It Mean?" (1985)

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Album: Schoolly D

Producer: J.B. Weaver, Jr.

Label: Jive



"P.S.K., we're making that green/People always ask what the hell does that mean?" rapped Schoolly D on this landmark, hardcore East Coast rap song. P.S.K. refers to the Park Side Killas, a notorious gang that the West Philly native was affiliated with, and the song is considered to be one of the earliest gangsta rap recordings to appear on wax. Ripe with images of violence, sex, and drug dealing, the song was also one of the earliest to feature the word "nigga." In addition to repping the 5-2 crew, both Schoolly D and DJ Code Money inadvertently kick-started a genre with a track that was well ahead of its time.

During the mid-80s, tapes of this classic were being sold at 52nd & Parkside in West Philly, right near the edge of Fairmount Park. The influence of the Park Side Killas' anthem extended beyond the city, influencing a young West Coast MC by the name of Ice-T, inspiring him to pen "6 'N the Mornin'." Samples of those familiar crash cymbals can be heard on Case's "Touch Me, Tease Me," Biggie's "B.I.G. Interlude," and even DJ Khaled's "It Ain't Over Til It's Over." The early purveyor of gangsta rap is also responsible for another tune that many of us are familiar with—the theme for Aqua Teen Hunger Force. Also, anytime you're mentioned by everyone from Ice-T to Primus, your OG status is set in stone.

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