*This article was originally published on November 28, 2022.

The 1990s were a defining decade for hip-hop both as a mass cultural movement and a vast commercial enterprise. As new superstars emerged from cities and neighborhoods around the country, the 90s saw rap music’s profitability and global reach increase exponentially. During this period, a thriving underground scene grew beneath (really parallel to) rap’s campaign of mainstream pop cultural dominance. This dynamic would play out here in Philadelphia as well with a handful of artists turning out major label releases while the majority recorded for small indie labels like IQ and Ragz To Riches, while playing local venues like Dances and The Fake Haus, and selling their own vinyl, cassettes, and CDs independently.

Not only did Philly hip hop in the 90s build upon the stylistic growth and evolution that it enjoyed in the 80s, but the 90s also set a clear path for the music’s future with many young artists making significant breakthroughs in the 2000s. It would be nearly impossible to compile a list of songs that would completely sum up Philly hip-hop in the 90s, but the following selection of songs is a sincere attempt at capturing the sound and style(s) that defined this chaotic and memorable decade.

Freshco & Miz – We Don’t Play (1990)

In 1989, Southwest Philly turntablist, DJ Miz, and Brooklyn lyricist, MC Freshco respectively won the DJing and rap contests during the New Music Seminar Battle for World Supremacy. After deciding to team up as a group, the duo dropped “We Don’t Play”, an electrifying, uptempo anthem that has been rocking cookouts and block parties since the day it came out.

Freshco & Miz - “We Don’t Play”

DJ Jazzy Jeff & The Fresh Prince – Summertime (1991)

When the video for DJ Jazzy Jeff & The Fresh Prince’s “Summertime” aired following an episode of The Fresh Prince of Bel-Air, the song was destined to be a hit and an enduring classic. With its uplifting hook, a hypnotic flip of Kool & The Gang’s “Summer Madness,” Will Smith’s laid-back flow, and a colorful video, “Summertime” perfectly captured the warm and playful side of life in Black Philadelphia.

DJ Jazzy Jeff and The Fresh Prince - Summertime

Tone Love – Bring It Home for Jerome (1992)

26 years before Meek Mill’s “Dreams & Nightmares” was taken up as the anthem for the Philadelphia Eagles’ 2018 Superbowl run, Tone Love of the Tuff Crew’s 1992 anthem “Bring It Home for Jerome” was the defacto soundtrack of the 1992 Eagles. Created in tribute to Eagles ProBowl defensive tackle Jerome Brown after he was tragically killed in a car accident in the summer of 1992, “Bring It Home for Jerome” was a musical rallying cry as the team built momentum for a playoff appearance before eventually being eliminated by the Cowboys.

Tone Love - Bring It Home for Jerome

The Roots – The Session (The Longest Posse Cut in History) (1993)

Clocking in at over 12 minutes, “The Session” acts as a lovely bridge between The Roots’ tendencies to jam out on extended live grooves and their connection to Philly’s diverse rap scene. A veritable cypher on wax, Questlove introduces each MC and we get standout verses from Black Thought, Shortie No Mass and members of the Roots extended crew, Foreign Objects.

The Roots - The Session (Longest Posse Cut In History)

Ruggedness & Madd Drama – For Real (1994)

“For Real” is an underground anthem from the Hunting Park rap crew, Ruggedness, and Madd Drama. Produced by triple threat MC/beatmaker/Engineer Ruggedness, “For Real” is as raw as it is otherworldly. The beat is dark and atmospheric and Ruggedness comes with an unhinged flow, delivering sing-songy lines and layered pop culture references.

Ruggedness Madd Drama - For Real

Bahamadia – Unknowhowwedu (1995)

Written as an extended shout-out to Philly hip-hop innovators past and present, Bahamadia’s “Unknowhowwedu” is a veritable Philly hip-hop family tree. Over Ski’s smooth, glowing instrumental, Bahamadia spins together verses that tell the story of Philly hip-hop culture throughout the 70s, 80s, and 90s. Early figures like Lady B and Sex Machine get love while 80s stars Tuff Crew and 3XDope are celebrated alongside 90s underground legends Ruggedness and The Rebels. It wouldn’t be a stretch to say that a vast portion of Philly hip-hop history can be traced and contextualized with just the names Bahamadia references in “Uknowhowwedu”.

Bahamadia - Uknowhowwedu

Da Fat Cat Clique – Da Flow (feat. E.S.T., The Man They Call Lux, Ital Tha Ruffian, Lavee, Ruggedness) (1996)

Da Fat Cat Clique’s “Da Flow” was an unlikely local hit. It wasn’t a single (the tune was the third cut on a 12” led by the much poppier cut “My Tracks”), and it was a posse cut with 7 MCs flexing their lyrical skill over a gorgeous but lowkey, piano sampling beat. Despite all this, “Da Flow” spent the summer of 96’ at the top of Power 99’s “Top 9 at 9” countdown, regularly beating out national hits like Junior Mafia and Notorious B.I.G.’s “Get Money.” Criz Diggity and A.B. Lover welcome E.S.T. of Three Times Dope, The Man They Call Lux, Ital Tha Ruffian, Levee, and the track’s producer, Ruggedness for a run of booth-burning guest verses and the result is a crazy accurate snapshot of the stylistically diverse state of Philly rap in the mid-90s.

Da Fat Cat Clique - Da Flow

D.O.D. – Price Of Fame (1997)

A bittersweet ode to life on the street, D.O.D.’s “Price of Fame” was in rotation on Power 99’s highly influential late-night mix show Radioactive, and the song remains an underground classic. With its gorgeous guitar and vocal sample, the song has a sad, introspective air. The lyrics touch on violence, depression, and desperation with Don Corleone ending his verse by demanding to be buried laying on his stomach when he dies so the world can “kiss my ass.” More than anything, “Price Of Fame” is brilliant because it captures the flipside of street life and the drug game.

D.O.D. - Price Of Fame

The Come Up Show Freestyle – Beanie Sigel, Philly’s Most Wanted and Major Figgas (1998)

Likely recorded sometime in 1998, Beanie Sigel, Philly’s Most Wanted and Major Figgas’ radio freestyle on Cosmic Kev’s The Come Up Show late-night mix show on Power 99 offered a glimpse of the future of Philly rap. Characterized by graphic lyrics, punchlines, and dexterous rhyme patterns based on internal rhyming couplets, the style that Beanie Sigel, Philly’s Most Wanted, and Major Figgas pioneered would provide a template for Philly’s next generation. Listening to this freestyle, it’s hard to imagine that 2000s-era Philly MCs like Meek, Reed Dollaz, Joey Jihad, and countless others would’ve sounded like they did without their forbearers. Also, this freestyle gets bonus points because Beans kicks the same verse that he would later use on The Roots’ “Adrenaline”.

Beanie Sigel, Philly's Most Wanted & Major Figgas Freestyle (Cosmic Kev)

Eve – What Ya Want (1999)

Armed with Swizz Beatz’s Latin-flavored instrumental and oozing charisma, West Philly native Eve’s “What Y’all Want” was a star-making debut. With supreme confidence and style, Eve came right out the gate and let us know that she was “Changing the game, setting the rules, making it work,” building upon the legacy established by Lady B, Malika Love, Evette Money, and other brilliant Women rappers from Philly.

Ruff Ryders - What Ya Want ft. Eve, Nokio

Bonus jawns, local hits, and underground classics.

Three Times Dope – No Words (1990)Cool C – Life In The Ghetto (1990)HanSoul – Imagination (feat. Veronica Underwood) (1991)Larry Larr – Larry That’s What They Call Me (1991)2 Kannon – Keep It Goin (1992)C.E.B. – Get To The Point (1992) Ebony Broadcast System – Skillz (1992) The Goats – Typical American (1992)Jon Doe & Rumble Town –Ease Back (1993)Bahamadia – Funk Vibe (1993)Divine Beings – Funky Ultimatum (1993)Big Tabb – It’s Nice Outside (1993)Tasc 4orce – Takin’ No Shorts (1993) Da Yonugstas – Crewz Pop (1993)Da Youngstas – Hip Hop Ride (1994) Sha’dasious – U Kant Play Me (1994)The Man They Call Lux – Gangsta (1994)100X Beyond The Door (1994)The Roots (feat. Mars Co-Op & Dice Raw) – Clones (1995)Tainted Mindz – Any Time Any Place (1995)Jamal – Fades Em’ All (1995)Pauly Yams & DJ Jazz – When I Blow Up (1995)Ram Squad – Keep It Real (1995) Ram Squad – Unfortunate (1996)Tracey Lee – The Theme (It’s Party Time) (1996)Prophets Of The Ghetto – Da Expansion (1996)Bahamadia (feat. The Roots) – Da Jawn (1996)Bahamadia (feat. Mecca Starr & K-Swift) – 3 Tha Hard Way (1996) The Last Emperor – Secret Wars Pt. 1 (1996)Jedi Mind Tricks ‎– Heavenly Divine (1999)The High & Mighty – It’s All For You (1997) Rasheed & lll Advised (feat. Pauly Yams) – (1998)Mountain Brothers – Galaxies (1998)Name – Logic (1998)Name – Essay Tee (1998)The High & Mighty (feat. Mad Skillz & Mos Def) – B-Boy Document 99’ (1999)