The 50 Best Radio Freestyles

We count down the greatest on-the-air freestyles from Eminem, Jay-Z, Big L, Biggie, and more.

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Complex Original

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While some might argue that radio is now a dying medium, it’s undeniable that the AM/FM dial was the first outlet to bring hip-hop to the masses. Starting in the early 1980s, pioneering DJs like Mr. Magic, Red Alert, the Awesome Two, and Lady B gave a voiceless community the chance to be heard, and inspired future generations to pursue rapping as their full-time occupation.

Since that time, many legendary hip-hop radio shows have sprung up around the world, and during those late-night or early-morning time slots a new art form was born: the radio freestyle.

Many of hip-hop’s greatest beefs were spawned live and direct over the airwaves. In the pre-MP3 era, cassette copies of these one-of-a-kind performances passed hand to hand, cementing reputations, and becoming the stuff of legend. Nowadays it's all done digitally, but the objective remains the same—total domination, no mistakes allowed.

Some great freestylers rose through the ranks to become rap superstars (Eminem), while others had their lives cut short before attaining their just rewards (Big L). Unknown rappers and weed carriers alike got the chance to show and prove alongside hip-hop’s elite, and sometimes a hungry upstart would outshine the master.

But let’s be honest—most rappers don’t actually freestyle their freestyles anymore. As technology advanced it's become easier to catch a rapper flubbing. Instead of risking public embarrassment, most prefer to write their rhymes ahead of time. Hell, some artists don’t even have the talent to go off top. Is it cheating? Well, the jury's still out on that one, but the lines have been blurred as to what a freestyle actually is.

From off-the-dome bars to spitting writtens, the definition of a freestyle has evolved over the years—but we draw the line at reading off of mobile devices. Bottom line: to earn respect in the rap game you have to prove yourself on radio. Fuck a blog, dog. Today, Complex takes you through the 50 Best Radio Freestyles of all time. Turn up your dial and tune in.

RELATED: Best 50 Rap Albums Ever Made

50. Kanye West & Common (Sense) "Freestyle Battle" (1996)

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Station: WHPK

DJ: Twilite Tone

Best Punchline: "If you was really cold/Why the fuck did Crucial Conflict go gold/And you only sold a hundred copies—to your boys."

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In 1996, Common and Kanye crashed The Twilite Tone's show at the University of Chicago's legendary station, WHPK, for an impromptu on-air freestyle battle. At the time, Kanye was an unsigned artist (as he reminds us several times throughout the battle), whose only claim to fame was placing some beats on an album by local artist Grav.


The fact that Com Sense even gave Kanye the time of day was a big deal. At the time he probably seemed like just an annoying bugaboo to the more established Chicago emcee. Hats off to both artists, as neither spit written verses while lambasting each other on various instrumentals for over ten minutes.


Kanye called Common “Senseless,” and clowned his lack of record sales: “If you was really cold/Why the fuck did Crucial Conflict go gold?/And you only sold a hundred copies—to your boys.” Common dissed Kanye for using the word 'herb' (“Herbs? Nigga we from Chi, we call 'em marks”) and claimed the beats Kanye gave Grav were “bull.” However the award for most hilarious line goes to Kanye, who mocked Com's O.G. nasally high-pitched voice (see “Take It EZ”): “Since you was 'ooh ooh ooh' just way wack.”


Common later admitted to Nardwuar that both emcees were drunk at the time, and that the battle was 100% friendly fire. And as you know, things have been all G.O.O.D between the two ever since.

49. J. Cole "Funk Flex Freestyle" (2010)

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Station: Hot 97

DJ: Funkmaster Flex

Best Punchline: “Nigga you wack, you should've fired whoever signed that/Cole introduced you to death and you kept in contact.”



Prior to shocking the world by selling 217,000 copies of his debut album in one week, J. Cole was on a seemingly endless promo tour, hitting the streets to prove himself as an artist. Sure he had the Jay-Z affiliation, but not everyone was convinced. In 2010, he did his best to change public perception by slaying NYC with this energized freestyle on Hot 97.


Effortlessly shifting from Rae's “Ice Cream” to $hort's “Blow The Whistle,” the Dreamvillian lived up to his own hype and proved that he was going to be a major player in the game.

48. Eyedea & Slug "Wake Up Show Freestyle" (2001)

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Station: KMEL/Power 106

DJ: Sway & Tech

Best Punchline: "I know that my mustache is dirty/But I'm 20, and with this, chicks think that I'm 30." (Eydea)



If skills sold, truth be told, the late-great Eydea would've been a rich and successful mainstream artist. But much like many of hip-hop's greatest freestyle rappers, he couldn't translate those skills into mainstream success.


Both Eydea and Slug were part of a small group of rappers who actually freestyle off the dome—something of a lost art nowadays. These two kids from Minnesota went back and forth for over eight minutes on The Wake Up Show, all while cracking jokes on each other and arguing about show dough.

47. Black Thought & Q-Tip "Dilla Dedication" (2010)

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Station: Shade 45

DJ: Tony Touch

Best Punchline: "Spotted on the red carpet stepping out a spaceship/With a glass of Chiraz and two around the way chicks." (Black Thought)



On the fourth anniversary of J. Dilla's passing, Tony Touch hosted quite the celebration in his honor. Tony's Toca Tuesdays boasted a DJ set from ?uestLove, and featured off-the-dome freestyles from Black Thought and Q-Tip. Busta Rhymes even called in to express just how dope the cipher was. The memory of Dilla lives on!

46. Cee-Lo "Wake Up Show" (2002)

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Station: KMEL/Power 106

DJ: Sway & Tech

Best Punchline: "Isn't that funny/You'll give a school all your money/For what you think you need/But it's never guaranteed"



Hey kids, I know this might come as a shocker, but the guy who sings “Fuck You” actually used to be a rapper. And he was good! On The Wake Up Show, Sway and Tech were able to convince Mr. Green to actually kick a rap, and it was pretty incredible.


Combining the best of his Goodie Mob sensibilities—knowledge, wisdom and understanding—Cee Lo's rhymes offered some actual food for thought. Sway went so far as to call his verses “profound.” This appearance makes us long for that Goodie Mob reunion that will most likely never happen.

45. David Banner & Bun B "First Meeting" (2003)

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Station: KPFT

DJ: Matt Sonzala

Best Punchline: "It's goes down I promise/It's goes down with me and David Banner and your baby mama." (Bun B)



On this fateful night in 2003, newcomer David Banner met Underground King Bun B for the very first time. As the story goes, Banner had driven from Mississippi to Houston in his van (where he was living at the time) to record “Like A Pimp,” his breakout (and Pimp C sampled) single, with Lil Flip.


While in Houston, Banner linked with Matt Sonzala to appear on Damage Control radio, and while at the studio he met one of his idols, Bun B. The two immediately hit it off, and teamed up to kick an off-the-dome freestyle over Lil Jon's “I Don't Give A Fuck” instrumental. The whole session was Southern-fried affair, with plenty references to lean, wood wheels, and grills.

44. EPMD "Marley Marl" (1989)

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Station: WBLS

DJ: Marley Marl

Best Punchline: "You're a part time sucker, who works O.T." (Parish)



While EPMD wasn't snappin' necks and cashin' large checks, they had to show love to NYC radio—and they did just that on Marley Marl's show on WBLS. Erick and Parish kicked some larger-than-life braggadocious bars, proving that this duo from L.I. were major players in the rap game.

43. Snoop & Xzibit "New York City Freestyle" (1999)

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Station: Hot 97

DJ: Funkmaster Flex

Best Punchline: “It ain't East or West, I want the whole world behind me/I've got brothers in L.A. saying eff Giuliani.” (Xzibit)



In the Fall of 1999, while on the promo trail for Dr. Dre's 2001, Xzbit and Snoop Dogg dropped by Funkmaster Flex's show on Hot 97 to bless the airwaves with their West Coast flow. Oddly enough, Dre wasn't in attendance, but who really wants to hear Dre freestlye anyway?


X-to-the-Z's career was having a resurgence thanks to his appearance on Snoop's single “Bitch Please,” so the two celebrated with a nine-minute freestyle over some of the best beats of the 1-9-9-9. And there's no better way to date that era than hearing Snoop shout out No Limit Records while X shows solidarity with the NYC hip-hop community: “I've got brothers in LA saying F Giuliani.” Still in Snoopafella mode, Snoop kicked one of his patented fairy-tale rhymes about a turned-out Little Red Riding Hood (No Ray J) and the Big Bad Wolf having a nasty blow habit.

42. Canibus & Journalist "DJ Clue Freestyle" (1998)

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Station: Hot 97

DJ: DJ Clue

Best Punchline: “I'll fly your body out of Dallas/Perform plastic surgery while we're airborne then switch caskets/And lie to the masses/I'll tell 'em you got murdered over some East West beef between rappers/Radio stations then expresses they sadness/Play records back to back, while passing out stop the violence pamphlets.” (Canibus)



Believe it or not, before becoming a punchline for failed rap careers, Canibus was one of hip-hop's fiercest and most promising emcees. So when 'Bis appeared on DJ Clue's Hot 97 show in 2000, it was no surprise that Germaine Propane set the microphone ablaze alongside his protege, Journalist.


This legendary eight-minute freestyle broke many rewind buttons on tape decks (at least among those who were still using cassette players at the turn of the century). Bars like these were why 'Bis was being championed one of the greatest of all time:


“Assassins camouflaged in the grass blastin'/Leavin blood all over your lady like Jackie O'Nassis/I'll fly your body out of Dallas/Perform plastic surgery while we're airborne then switch caskets/And lie to the masses/I'll tell 'em you got murdered over some East West beef between rappers/Radio stations then expresses they sadness/Play records back to back, while passing out stop the violence pamphlets.”


This virtuoso performance had fans geeked for Canibus' sophomore album, but unfortunately for 'Bis, that second album was his second round K.O. 2000 B.C. flopped even harder than its predecessor, Can-I-Bus. Things didn't fare much better for Journalist, who not only had a bum name, but also got stuck as a weed carrier (sorry!) for the greatest emcee to never realize his full potential.


All jokes aside, though, Canibus murdered the airwaves and—for a few minutes—proved he was worth every bit of hype and acclaim.

41. Stetsasonic "Mr Magic" (1986)

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Station: WBLS

DJ: Mr. Magic

Best Punchline: "You wear your white flag in a call to surrender/Sucker MCs posin' as contenders/I'll write you off and back home I send ya.” (MC Delite)



With beat boxing courtesy of Wise-O (a.k.a. the Human Mix Machine)—who perfectly mimicked the bassline from Marva Whitney's “It's My Thing”—Daddy-O, Frukwan and MC Delite shut down Mr. Magic's classic Rap Attack show.


Back in the mid-80s, hip-hop on the radio was very rare, so to hear a cutting-edge rap group using such advanced sonic techniques was pretty much a revolutionary concept. Stet repped their various neighborhoods and boroughs, and showcased this new form of music in a relentlessly positive and fun light.

40. Jay-Z "700 Percent" (2005)

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Station: Hot 97

DJ: Funkmaster Flex

Best Punchline: “I put a couple careers on hold, you could be next, kid."



While Jay-Z radio freestyles are now few and far between, back in the mid-aughts, Jay had a lot to say, especially to those who lifted his lines for their hits. Jay warned, “Do not put my verse on your records,” which is a kettle/black situation, as Jay had been lifting Biggie bars for years.


This freestyle is notable as it was the first time we heard his “Dear Summer” verse, and the “I put a couple careers on hold, you could be next, kid” line, which was no doubt aimed at Jayceon Taylor. Jay is undoubtedly the king of subliminals, and although he never directly calls out Game by name, peep how many times he says game within the four minutes.

39. Kurupt & Ahmad "Wake Up Show" (1994)

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Station: KMEL/Power 106

DJ: Sway & Tech

Best Punchline: Getting ready to drop the bomb like the B-1/Your 140 pound rhymes and mines are three tons.” (Kurupt)



These days Kurupt is often criticized for reaching with his rhymes, but in the '90s there was no denying the fact that he was one the best and most focused in the game.


Legend has it that Kurupt once served 2000 MCs live in a battle, so he was able to rock The Wake Up Show (off the dome) with ease. The far superior Kurupt left Ahmad sounding silly, making it perfectly clear why “Back In The Days” was his one and only hit.

38. Eminem & Proof "Tim Westwood" (2000)

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Station: Radio 1

DJ: Tim Westwood

Best Punchline: Give me 11 Excederin my head will spin/Medicine will get me revving like a 747 jet engine.” (Eminem)



Eminem and Proof always had natural chemistry while rocking the mic together—no doubt from their early days freestyling at Detroit's famed Hip-Hop Shop.


This appearance on Tim Westwood was notable as it was the first time we heard Em's bars from his Soundbombing contribution “Any Man,” including the dizzying: “Give me 11 Excedrin/My head will spin/Medicine/Will get me revving like a 747 jet engine.”


The late-great Proof was no slouch either blurting out hilarious lines like: “I'll make R. Kelly confess he stole his first style from Aaron Hall.”

37. Big Daddy Kane "Juice Crew" (1989)

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Station: WBLS

DJ: Marley Marl

Best Punchline: “So toss the sauce, across to the boss/No remorse, with force I cause a holocaust.” (Big Daddy Kane)



Although the Juice Crew took an L in the Bridge Wars, they still found great success in hip-hop's early years. And none more so than Brooklyn's own Big Daddy Kane—a strong contender for G.O.A.T. of the Golden Age.


Rumors swirled in that era that Big Daddy Kane and the great Rakim had a beef on wax, substantiated by many subliminal (and not-so subliminal) shots on records. Although, BDK claimed there was never any real static between the two factions, this freestyle was littered with shots that could've easily been directed at the R.


While each MC brought their a-game on this freestyle (Craig G killed it), it was clearly Kane who ruled the roost.

 

36. MC Juice "Sway & Tech Freestyle" (Late '90s)

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Station: KMEL/Power 106

DJ: Sway & Tech

Best Punchline: "I attract light like photosynthesis/Rappers are wack as hell and I'ma put it in parenthesis/No pause or comma cause I'm a keep you fearing this/You gotta question mark, I'm the nigga here period."



Chicago's MC Juice is quite possibly the most underrated freestyle rapper of all time. The fact that he narrowly defeated a young Marshall Mathers in the championship round at Scribble Jam in 1997 should guarantee a spot in the record books alone.


In the late '90s, the Windy City emcee spent a lot of time on the West Coast, appearing numerous times on Sway & Tech's Wake Up Show. While all of his appearances were head turning, it was this freestyle in particular that solidified Juice as one of the G.O.A.T. at coming off the dome.


Unfortunately, Juice never got the mainstream success he deserved, but ask your favorite rapper's favorite rapper and they'll tell you Juice can crush anyone in a battle.

35. Fabolous "Soulja Boy Diss" (2010)

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Station: Hot 97
DJ: Funkmaster Flex
Best Punchline: “Pretty boy swag, never coke my nose, though.”



It's no secret that Fabolous is a cyber bully. If you get caught doing the dummy, Fab will be quick to call you out on those social networks. Before beefing with Ray J and the #MoneyTeam, Fab was cracking jokes on Soulja Boy for getting caught in a coke scandal with public enemy jumpoff No. 1, Kat Stacks.

After having it out on Twitter with Soulja Boy (before 50 Cent intervened), Fab dropped by Funk Flex's show to kick a freestyle littered with some not so subliminal bars for Mr. Crank That.

Although the whole freestyle wasn't completely centered around Soulja Boy (Brian Pumper took a few shots as well), it was enough to be thankful DeAndre didn't have seven phantoms sitting outside of Hot 97 waiting on Fab.

34. Kool Keith "Marley Marl" (1989)

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Station: WBLS

DJ: Marley Marl

Best Punchline: “You got the birdie disease, by eating rhymes that I have for ya/The poison is bad for ya, stupid”



Listening to Kool Keith's a capella freestyle on Marley Marl's WBLS show, many people probably assumed that the always bizarre Ultramagnetic MC was simply rapping about everyday household pests: bugs, birds, and doves. But taking a closer look, Keith was using these creatures as metaphors to describe rhyme animals who dared to bite. Most rappers love to claim that others jocked their style, but how many actually described them as creatures you could find in your backyard? Bugged out, indeed.

33. Jadakiss "It Ain't Hard To Tell Freestyle" (2004)

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Station: Hot 97

DJ: Funkmaster Flex

Best Punchline: "A real man shouldn't have to say No Homo.”



In the summer of 2004, Kiss was on the promo trail for his Kiss Of Death album, and he and the D-Block gang stopped through Funk Flex's show to rock over Nas' “It Ain't Hard To Tell” instrumental.


Kiss kicked those gritty bars about the trife life, sprinkled with subliminal shots at some unlucky foe. Many speculated Kiss was firing off at Dipset with the “A real man shouldn't have to say No Homo” line. Because let's be honest, they were the only crew using that phrase at the time.


Flex cites this freestyle as one of his top five favorites, and with quotables like: “It's all simple mathematics/I eat half off rap and half off addicts” it's no surprise.

32. A Tribe Called Quest "Angie Martinez Freestyle" (1995)

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Station: Hot 97

DJ: Angie Martinez

Best Punchline: "You couldn't converse if you had f'ing React juice.” (Phife)



By 1995, the dynamic of A Tribe Called Quest had changed completely. Rumors swirled that the tension between Q-Tip and Phife Dawg was thick, beats were being handled by a new producer named JayDee, and a new member, Consequence, was introduced.


Debuting this new lineup, Tribe hit Angie Martinez's show to represent for the latter-day Native Tongues movement. And Despite what we'd heard about their internal strife, the kids from Queens kicked it all of the way off. The new guy wasn't half bad at rapping either.

 

31. Slaughterhouse "D.O.A. Freestyle" (2009)

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Station: Shade 45

DJ: Green Lantern

Best Punchline: “I'm in a zone of my own, my condolences/To anyone or any group that's opposing this/This ain't that, this a movement we controlling this/You can't beat us, we don't want you to join us, so get over bitch.” (Joell Ortiz)

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After announcing that Slaughterhouse was officially a group, the fantastic four appeared on Green Lantern's Invasion show to let listeners know what these beastly beings were capable of. For upwards of 20 minutes, they bodied Jay-Z's “Death of Autotune” instrumental, but it was Joell Ortiz's verse that left heads spinning and sent other so-called lyricists back to the drawing board.

30. Kool Moe Dee "Awesome Two" (1988)

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Station: Awesome Two Radio

DJ: Awesome Two

Best Punchline: “Jack...the Ripper, down with my zipper/You get paid to be a Moe Dee tipster/Tryna knock the way I rock/Get off my jock/'ma knock you out the box.”



Opinions vary on who won the battle between LL Cool J and Kool Moe Dee, although general consensus leans toward LL. Not for nothing, Moe Dee gave Cool J quite the run, and was relentless in trying to defeat his arch nemesis. A forgotten piece of this saga, is Kool's “Awesome Two” freestyle where he attacks Cool James aggressively for over three minutes.


Moe Dee truly sounded as angry as Pac on “Hit Em Up,” at one point even claiming: “I'ma eat that boy up, boy.” (Pause that up.) “Jack...the Ripper, down with my zipper/You get paid to be a Moe Dee tipster/Tryna knock the way I rock/Get off my jock/'ma knock you out the box.”

29. Cam'ron & Juelz Santana "Fuck You Freestyle" (2000)

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Station: Hot 97

DJ: Funkmaster Flex

Best Punchline: “Mase went to church, settled down, imagine it/Who me? Devil's advocate.” (Cam'ron)



Over the Lox's “Fuck You” instrumental, Cam'Ron and his then-unknown protege Juelz Santana, rocked Hot 97 with their Harlem-infused verses. Yeah Cam killed per usual, but it was the new jack Santana who surprised with his dizzying wordplay, “You think a good job is makin' 25 an hour/Got cats sellin' 25, 25's an hour/And I'm the one paying them 25 an hour/25 for rock and 25 for powder.”


And it was the first time Cam spoke on former friend Mason Betha's short-lived retirement: “Mase went to church, settled down imagine it, who me? Devil's advocate.”

28. Big Pun "Stretch & Bobbito" (1995)

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Station: WKCR (89.9FM)

Dj: Stretch & Bobbito

Best Punchline: "Still I will remain a pain inflictor/Giving you hell to bring to victors/Comin to getcha/Playin the game the same as Hitler.”



Before Chris Rios was capitally punishing the industry, he was Joey Crack's secret weapon—a rap assassin in training. Pun wasn't crushing a lot at the time, but Joe still brought him up to Stretch & Bobbito's show on WKCR FM—the birthplace of countless legendary freestyles by future rap icons—to flex his lyrical muscles.


With Joe cheerfully coaching him, Big Punisher dismantled the microphone, leaving it smoking with this quick yet effective freestyle. It was hard to argue that Pun was a beast after this display of next-level wordplay: “Still I will remain a pain inflictor/Giving you hell to bring to victors/Comin to getcha/Playin the game the same as Hitler.”

27. Fabolous & NORE "Fab's First Freestyle" (1998)

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Station: Hot 97

DJ: DJ Clue

Best Punchline: “Who in the club without a weapon/Shoot at your feet, make you do the Puff dance with perfection.” (N.O.R.E.)



Back in 1998, the somewhat unlikely pairing of N.O.R.E. and BK newcomer Fabolous Sport, appeared on Hot 97 to freestyle with DJ Clue. N.O.R.E. was bubbling across the globe thanks to his solid solo debut, and Fabolous was trying to carve out a name for himself in the overcrowded NYC scene.


The brand new F-A-B-O held his own on the airwaves, but it was N.O.R.E. who stole the show with entertaining lines like: “Who in the club without a weapon?/Shoot at your feet, make you do the Puff dance with perfection.” Even more hilariously, he claimed he was “The next Suge Knight”—something most wouldn't have dared to do in the '90s.

26. Lord Finesse "Stretch & Bobbito" (1990)

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Station: WKCR (89.9FM)

DJ: Stretch & Bobbito

Best Punchline: "You can't escape the inconceivable/Niggas are so wack even people who read braille ain't feeling you."



Plenty of hip-hop fans champion Big L as one of the greatest lyricists of all time, but what they fail to do is trace his roots and influence back to his mentor, Lord Finesse. The Bronx-born leader of the DITC was the man who arguably fathered L's style.


Finesse was a mainstay on Stretch & Bobbito's show over the years, but listening to him spit in 1990, it's clear where a lot of NYC rappers lifted their punchline delivery technique. Finesse was steppin' to the '90s, and a whole city followed suit.

25. Redman & Keith Murray "Enigma Freestyle" (1996)

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Station: Hot 97

DJ: Funkmaster Flex

Best Punchline: I'll serve famous Keith Murray beef curry/Scattered rappers on plaques.” (Keith Murray)



While out doing promo for Keith Murray's Enigma album, Reggie Noble and the most beautifullest MC in the world hit Hot 97 to kick an uncensored freestyle that lasted for 15-plus minutes.


These Def Squad brothers showed their lyrical dominance, and lack of respect for other crews: “I'll serve famous Keith Murray beef curry/Scattered rappers on plaques.”


Later, the always entertaining Redman kicked: “I wouldn't leave a trace if I died and police chalked me.” In the 9-6 there weren't too many seeing the Def Squad, and that's actual facts.

24. Eminem "Wake Up Show" (2000)

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Station: KMEL/Power 106

DJ: Sway & Tech

Best Punchline: “I smoked crack today, yesterday, and the day before/Saboteur, walk the block with a Labrador/Strapped with more coral for war than El Salvador/Foul style galore/Verbal cow manure/Coming together like the eyebrow on Al B. Sure.”



When Eminem first burst on the scene in 1999 with “My Name Is,” those not in the know probably assumed he was just an edgier version of a boy band member. Little did they know, Em was one the underground's greatest battle and freestyle rappers. It was this appearance on The Wake Up Show that helped Eminem catch the attention of Dr. Dre and Jimmy Iovine.


After signing on the dotted line, the Detroit emcee proceeded to pull off an almost impossible feat, becoming the only rapper to successfully dominate the pop charts as well as the underground battle rap circuit. Somehow Em was able to walk that fine line, appealing to casual rap fans as well as snobs with his hilariously layered lines.

23. Cassidy "11 Minute Freestyle" (2004)

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Station: Hot 97

DJ: DJ Enuff

Best Punchline: "I aint' no pretender, ya remember the Free stuff/And that'll happen to any nigga think he tough."



In 2003, Cassidy was little more than a mixtape rapper with a cosign from Swizz Beatz. Sure, we'd heard a few loose tracks, and caught wind of rumors that he'd dismantled Freeway in a freestyle battle. But by 2004, Cass had a single with Kells, and was starting to ring bells. Still, it wasn't until he kicked this 11-minute freestyle on Hot 97 that we recognized just how serious he was.


Cassidy beasted over some classic instrumentals while Swizz did what he does best—ad-libbing and hyping up the crowd. The combination was sheer musical mayhem.

22. Snoop Dogg & Dogg Pound "Deep Cover Freestyle" (1994)

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Station: Radio 1

DJ: Tim Westwood

Best Punchline: “Ah, I'm somewhat brain-boggled, so I look to the microphone and slowly start to wobble/It's S-N-Double-O straight to the P/Last four letters are D-O-Double-Geee/I'm the smoothest/I proved this/Many years ago.” (Snoop Dogg)



Dr. Dre ushered Snoop Dogg into the music industry, so it was only right that Snoop paid it forward, and introduced the world to Tha Dogg Pound. Back when Death Row was running this rap shit, Snoop, Daz and Kurupt traveled to London touching down with the UK's No. 1 rap representer Tim Westwood.


Although most of the lyrical heavy lifting was handled by Snoop, they all ripped the “Deep Cover” instrumental. But when Westwood dropped Tribe's "Award Tour" instrumental, the freestyling went to another level. Kurupt's performance made it evident that he'd be a force to be reckoned with on the lyrical tip, while Daz brought a fun-but-gangsta vibe to the beat that he rode so eloquently.

21. Super Natural "Words" (1993-94)

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Station: WKCR (89.9FM)

DJ: Stretch & Bobbito

Best Punchline: "Brains expand when I gets busy on the flex/Who's next?"



Supernatural is widely regarded as one of the greatest freestyle rappers of all time. Although, he never found mainstream success (read: sold albums), he's maintained a successful career on the performance circuit and remains a staple at festivals such as Rock The Bells.


Supernat's claim to fame is taking words or items people toss him during his freestyles, seamlessly incorporating them in his rhymes in real time. On Stretch & Bobbito's show, he flaunted this ability by flawlessly integrating such random and bizarre words as: “tasty cupcakes,” “yellow teeth,” “skinny bones,” “Haitian women” and “receding hairlines,” into a dazzling five-minute freestyle.

Being able to rhyme words that make no sense is fairly easy to do, but making coherent raps out of them is a whole other matter, and nobody does that better than Supernat.

20. Children of the Corn "Stretch & Bobbito" (1994)

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Station: WKCR (89.9FM)

DJ: Stretch & Bobbito

Best Punchline: “Stacks I'm betting 'em, bitches I'm deading 'em, perps I'm wetting 'em/Niggas buying records while I'm setting 'em.” (Cam'ron)



Picture this: at one time the collective of Killa Cam, Big L, Murder Ma$e (P. Diddy named him pretty!), McGruff and Bloodshed were searching for a record deal to no avail. Yep, Harlem's Children Of The Corner were possibly the best rap group that never really happened. Although they made dozens of hot records, the group hit about four years too early.


Before disbanding in search of solo success, the Children dropped by Stretch & Bobbito's show to demonstrate how they rock in Harlem World. While we all have a good laugh hearing Mason Betha kicking that tough talk, it was Cameron Giles who came with the killer quotables: “Stacks I'm betting 'em, bitches I'm deadin' 'em, perps I'm wettin' 'em/Niggas buying records while I'm settin' 'em.”


Unfortunately, two of the former group members (Big L and Bloodshed) are now deceased, so we'll never get to see a proper reunion. Not that we need another comeback from Mase or anything.

19. KRS-One "Red Alert" (1989)

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Station: WRKS 98.7 KISS FM

DJ: Red Alert

Best Punchline: "The most ancient man, was found thousands of years before Adam began/And where he was found?/Again they can't laugh at ya, is right dead smack in Africa/But due to religious and political power/We must be denied the facts every hour."



Letting us know that BDP "rules every single day of the week," KRS hit Red Alert's show on Kiss FM, to spit his philosophy. Since Red Alert's show was always competing with what Mr. Magic and Marley Marl were doing down the street, the BDP frontman had to murder everything moving (on the microphone, that is.)


Back in that era, KRS was at the height of his powers as a well-respected emcee speaking to a generation of disenfranchised youth. On this rhyme in particular, he was able to touch on Egypt, Adam & Eve, Greek culture, early civilization and religion—a far cry from his “I WAS THERE” attitude and rhyme subject matter of today. As his name implies, for KRS, Knowledge Reigns Supreme.

18. The Lox & Drag-On "The Lox Join Ruff Ryders" (1999)

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Station: Hot 97

DJ: DJ Clue

Best Punchline: "For the cause, we could go to more than war/We could put the guns down and take it back to swords." (Styles P)



After the “Let The Lox Go” campaign successfully freed Sheek, Jadakiss and Styles P from Diddy's reins, they hit Hot 97 to celebrate with DJ Clue. The foursome kicked that ryde or die shit—even the oft-maligned Drag-On was spitting the opposite of H20.


If you've ever wondered why they called Styles P the hardest out (pause?), look no further than his first verse. Kiss later kicked some of his educated street knowledge, and even flipped the bird at the IRS. Now that's reckless.

17. Eminem & Kon Artis "Tim Westwood Relapse" (2009)

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Station: Radio 1

DJ: Tim Westwood

Best Punchline: "Jason mask is off/But my face is plastered in Tabasco sauce/Spitting flames kicking fire out your ass...dog, you don't want to get my ass ticked off." (Eminem)



While on a European press run in 2009 for Relapse, Marshall Mathers and Denaun Porter dropped by Tim Westwood's studios and kicked an eight-minute freestyle reminiscent of the ones Em used to spit on-air pre-2000 (back when Marshall would rhyme at the drop of a hat). After a long struggle with addiction clouded his mind and hampered his creativity, this freestyle announced Shady's return to championship form.


Even his most simplistic rhymes were hilarious: “I'm quite mellow, a white fellow/My pee is bright yellow, I like Jello/I'm like hello,” but towards the end of his freestyle, he got way more technical, showing off with verbal attacks like: “The neurosurgeon, coke mirrors, I'm lyrics worse than/The kinda person to get Katie Couric to curisn'/Eighty spirits of ladies cause Shady murdered the virgins.”


Bottom line: the industry might consider Em a pop star, but he was still an emcee first.

16. DMX, Noreaga, Canibus "Rap's New Generation" (1997)

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Station: Hot 97

DJ: Funkmaster Flex

Best Punchline: "Ambushing MCs, jumping out the trees / Like Vietnamese in fatigues covered with leaves." (Canibus)

Part 1



Remember when DMX, Noreaga and Canibus were three of the hottest commodities in hip-hop? All three appeared on The Source's fold-out cover in June of 1998, proclaiming them "Rap's New Generation." (Hey Silkk!)


Celebrating this honor, the three amigos went on Funk Flex's show for an on-air cypher that lasted over a half hour and aired completely commercial free. Each emcee had a distinct and unique style: Canibus wielded his superior wordplay, DMX displayed his grimy and gritty side, and N.O.R.E. played the comedic role.


Each of these rappers has suffered ups and downs since '98, but for this moment in time, all eyes were on them.

15. Ras Kass, RZA, & Ol' Dirty Bastad "Wake Up Show" (1998)

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Station: KMEL/Power 106

DJ: Sway & Tech

Best Punchline: "F they whole battalion/I chop your head off and wear your skull iced out for a medallion." (Ras Kass)



Ras Kass, RZA and Osirus together on The Wake Up Show? Yeah, that sounds kind of random now, but do remember that Ras Kass and the RZArector were working together rather closely back in 1998. And you never really knew when or where Dirty McGirt was going to pop up.


Although RZA was in Bobby Digital mode (did he have his mask on?) he didn't actually rhyme. If it's any consolation, he did serve as a master of ceremonies "blasting mad thoughts to y'all" and even offered his trademark “skoo dooo doooo doooo” noise.


A relatively sober and coherent Big Baby Jesus was able to master his unorthodox and very random flow: “I turn white boys to Sprinsteen, Spruce,” while Ras Kass's mind-bending bars definitely left heads scratching: “I write my rhymes in alien/And battle fools in sign language.”

14. State Property "Hot 97 Takeover" (2002)

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Station: Hot 97

DJ: Funkmaster Flex

Best Punchline: "Niggas ain't messin' with the Roc/You can't scream D-Block, the same time connected with the cops" (Young Chris)

Part 1



Before self-imploding once the Roc crumbled, the State Prop Chain Gang, had one of the most stacked crews in hip-hop. There is power in numbers, and this conglomerate was ready for war with the entire industry. Rocking out for almost a half an hour on Hot 97, State Property blazed the airwaves with their grimy Philly bars, and roasted adversaries like Jadakiss, D-Block and Nas. All on New York radio. Philly was definitely in the building that night.

13. Hieroglyphics & Hobo Junction (1994)

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Station: KMEL/Power 106

DJ: Sway & Tech

Best Punchline: “Nigga you still play Pictionary with mom and dad/You grew up with wing dings named Buffy and Brad/You used to talk like this, 'That's rad let's go surfing.'" (Saafir)

Part 1



Back in 1994, two of the Bay Area's two most promising crews, the Hieroglyphics and Hobo Junction, squared off for an real live freestyle battle on San Francisco's famed KMEL. There was said to be static between the two factions, allegedly due to Casual not honoring a feature he'd promised for Saafir's Box Car Sessions album.


While the Hobo Junction are widely regarded as the victors, the Hieroglyphics have always contested that Saafir and crew were spitting writtens, so it wasn't an equal playing field.


While the winner of the battle remains debatable, the fact that Saafir crushed Hiero's street credibility wasn't: “Nigga you still play Pictionary with Mom and Dad/You grew up with wing dings named Buffy and Brad/You used to talk like this, that's rad let's go surfing.”

 

12. G-Unit "Shyne, Lil Kim Diss" (2003)

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Station: Hot 97

DJ: Funkmaster Flex

Best Punchline: "I heard Irv tried to sign Shyne, so I ain't got no love for him/Tell'em 50 said he soft, he won't shoot up the club again." (50 Cent)

Part 1



After having a breakout year in 2003, 50 accumulated everything he'd ever desired: rap superstardom and piles of money. Hate it or love it, the underdog was on top. Did the success calm Curtis, and stop him from attacking other rappers? Actually, it did quite the opposite.


With the Guerrilla Unit in tow, 50 dropped by Funkmaster Flex's show and fired off on a whole new cast of characters, including then–jail bird Shyne. And despite scoring a huge hit with Lil Kim on “Magic Stick,” 50 went on the offensive, cutting deeper than any plastic surgeon: “I wrote Magic Stick/I gave Kim a hit/ When I wouldn't shoot the video, she threw a lil' fit/Got emotional and shit/ Now this I don't get/ Why would I care about your emotions?/You're not my bitch.”


The freestyles were so slanderous, Flex finally had to cut them off and declare, “This is all in fun and music.”

11. Nas "H To The Omo" (2001)

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Station: Hot 97

DJ: Funkmaster Flex

Best punchline: "Is he H to Izzo, M to the Izzo/Fa shizzle you phony, the rapper version of Sisqo."

After Jay-Z took his long-simmering beef with Nas public with the shot heard round the world at Hot 97 Summer Jam 2001 (which we documented in our 50 Best Hip-Hop Diss Songs list): “Ask Nas he don’t want it with Hov. Nooo!”


Nas had no choice but to clap back at Jay. And after a few questionable lines from Memphis Bleek, Nas was ready for war with the entire Roc-A-Fella team: ““Rip the Freeway/Shoot through Memphis with Money Bags/Stop in Philly order cheese steaks and eat Beans fast."


The next line, however, was the one that ruffled Jay’s feathers and no doubt led to “Takeover”: “Is he H to Izzo, M to the Izzo/Fa shizzle you phony, the rapper version of Sisqo.”


Nas went on to call Jay the “Fake King of New York,” clowning him for having no priors and rapping like the Fu-Schnickens. Some thought Nas fell into Jay’s trap—hook, line and sinker, but what can’t be disputed is that this freestyle marked the start of the greatest hip-hop battles of all time.

10. Notorious B.I.G. & Lil Cease "Last Freestyle" (1997)

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Station: KMEL/Power 106

DJ: Sway & Tech

Best Punchline: "I make your mouthpiece obese like Della Reese."



Just six days before he was tragically murdered in Los Angeles, Biggie Smalls visited San Francisco's KMEL for his last recorded radio interview. Sway & Tech were able to get B.I.G. to dish on Tupac's death, Puffy, and the East vs. West Coast beef. Luckily they also convinced Frank White to kick a freestyle alongside his protege Lil Cease—actually he didn't need much convincing. As usual, Biggie was ready to go.


Sure his bars were borrowed from Life After Death, but the world had yet to hear the record. This definitive freestyle would become an important piece of hip-hop history, nonetheless.

9. LL Cool J "It's Yours" (1985)

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Station: Power 99

DJ: Lady B

Best Punchline: “If you're a sucker rapper, I'll name you Snoopy/Turn your girl into a Cool J groupie/Beat you in the face until the shit looks goofy/Then fuck your girl 'til she has to dookie.”



It's hard to believe that the man responsible for this dizzying freestyle was only 17 years old. That would put LL closer to Bow Wow's debuting age than Jay-Z's. The young prodigy was rapping better and more passionately than almost all of his elders, and kicked a new style, more technical than that of, say, the Sugar Hill Gang.


While on a promo run in Philly for his 1985 debut, Radio, Cool James blazed the airwaves and crushed all preconceived notions of what a rapper (a kiddie rapper at that) was supposed to sound like. He also took T La Rock's hit and made it his own, leading Def Jam to ask “T La who?”

8. Big L "1998 Freestyle" (1998)

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Station: WKCR (89.9FM)

DJ: Stretch & Bobbito

Best Punchline: "Turn your tux red, I'm far from broke, got enough bread/And mad hoes, ask Beavis, I got nothing Butthead."



A freestyle so dope, it was featured on Big L's breakthrough (and unfortunately posthumous) album, The Big Picture. L kicked this freestyle live on Stretch & Bobbito's show just months before he was tragically gunned down in Harlem.


L claimed his lyrics weren't directed at anyone particular, but it's evident he had someone in mind when kicking kill-yourself lines like: “Fuckin' punk, you ain't a leader/What? nobody followed you/You was never shit/Your mother should've swallowed you” over Lord Finesse's piano loop.


What many don't know, is that the freestyle actually included two verses, the second of which was omitted from The Big Picture. Perhaps after dropping the “And mad hoes, ask Beavis, I get nothing but head (Butthead)” line, Rawkus figured no more needed to be said.


And yeah, this was pretty incredible for someone who was “kinda tired.”

 

7. Roc-A-Fella "Hot 97 Takeover" (2001)

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Station: Hot 97

DJ: Funkmaster Flex

Best Punchline: "Squad Mobb Deep and we creeping on a quiet storm, give up the goods or sleep on a quiet storm." (Beanie Sigel)

Part 1



Back when Roc-A-Fella was still the army (better yet the Navy), Hov brought his shooters up to Hot 97 so they could bless the NYC airwaves. State Property was freshly inked to the Roc, so it was the perfect opportunity for Hov to show the boys from Philly some brotherly love in the Big Apple. Memphis Bleek, Beanie Sigel, Freeway, Oschino, Sparks, Young Chris and H Money Bags (who?), all graced the mic for an uninterrupted half hour. And hey, they even rocked over a few of their future foes instrumentals (“Keep It Thoro” and “Oochie Wally”).


Each MC brought their A-game, but it was the incredibly hungry, focused and energized Freeway who vocally proved that he'd earned his spot on the Roc. On this night, Free was the obvious standout, but this takeover was Jay's way of letting the world know he had a dynasty on his hands.

6. Nas & The Bravehearts "Prematic Freestyle" (1993)

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Station: WKCR (89.9FM)

DJ: Stretch & Bobbito

Best punchline: "Touch a temple/And leave you leaking when I'm speaking/Cause shit that I be freaking gets me papers when I'm sleeping."

 

It’s hard to remember a world pre-Illmatic. But believe it or not, there was a time when Nas was just a new jack vying for a spot in the hip-hop landscape.


Back in late-1993, an early incarnation of the Bravehearts (Nas, Jungle & Wiz) made their way from Queensbridge up to Stretch & Bobbito’s show, in part to promote Illmatic, which was due to hit stores in a few months. This threesome from the 40th side were relatively unknown but their front man, Nas, had a promising buzz thanks to a few high-profile appearances (“Live At The BBQ”) and a newly buzzing single (“It Ain’t Hard To Tell”).


With Nas describing Illmatic as “it’s just science, a bunch of sciences,” they all split time on the mic, but it was Nas who distinguished himself with lines like: “Here’s my basis/My razor embraces many faces/Your telephone blown, black stitches and fat shoelaces.” It’s almost unfathomable that the kid kicking those lines was only 20 years old.

5. Wu-Tang Clan "Stretch & Bobbito" (1993)

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Station: WKCR (89.9FM)

DJ: Stretch & Bobbito

Best Punchline: "Radio today is faking moves with the airplay/So I paved my own way to get a fair say." (Inspectah Deck)



The Wu swarmed the studios of 89 Tec 9 WKCR just months before their seminal debut album, Enter the Wu-Tang (36 Chambers), hit stores, shocking Stretch and Bob with their sinister Shaolin style. Griminess and raw energy bled through the airwaves as Method Man, Inspectah Deck, Raekwon, Ghostface Killah & GZA all took turns beasting off the dome.


The five participating members took the “Method Man” instrumental to task, and although some of their bars were later recycled on 36 Chambers, it was clear these bees had uncanny rhyming abilities.


This diverse group of newjacks boasted unique personas—from the charismatic star power of Method Man to GZA with his sharp and calculated bars, each member brought something different to the table. At the end of this freestyle it was obvious this rowdy collective was on to something special.

4. Jay-Z "Grammy Family Freestyle" (2006)

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Station: Hot 97

DJ: Funkmaster Flex

Best Punchline: "Everybody look at you strange, say you changed/Ugh—like you worked that hard to stay the same."



On Devil's Night 2006, unstoppable Hov dropped by Hot 97 to appear on Funkmaster Flex's show and promote Kingdom Come—Jay's first album since his short-lived retirement.


At the time, Jay was still parked behind a desk as President of Def Jam Records, so it was no surprise that a handful of artists on the label were less than pleased that their boss's LP was immediately made a priority. In the interview with Flex, Jay addressed disgruntled Def Jam acts LL Cool J and Method Man, as well as longtime adversaries Jim Jones and Cam'ron.


Afterwards, inspired by Basquiat with his chariot on fire and his mind on Pluto, Hov not only kicked one of the best freestyles of his illustrious career, but some of his most vigorous rhymes ever. Over Kanye's “Grammy Family” instrumental, Jay started by poking fun at the Dipset's label home, “I'm so independent I might buy Koch.” He went on to reflect on Martin and Malcolm, Big and Pac, Jesus and Judas, and the perils of success—lines that would later wind up in his song "Most Kings.”


Jay was back in a major way, and the almost-five-minute freestyle counted dozens of quote-worthy lines. While many of Jay's enemies saw the God MC as vulnerable and soft due to his shiny new job title, this freestyle proved he hadn't missed a step. The only part we can't figure out is why he didn't spit bars like these on Kingdom Come.

3. The Notorious B.I.G., Puff Daddy, & Craig Mack (1994)

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Station: Radio 1

DJ: Tim Westwood

Best Punchline: "Try me, die G, dangerous/Since my daddy bust me out the tip of his dick/Biggie Smalls was the wickedest shit."



Back when the B.I.G. Mack campaign was in full effect, hip-hop's Bad Boys jetted to the United Kingdom to promote their albums and plug a few parties—all while “Doing their thing and keeping it real.”


Craig Mack, Biggie and Puff Daddy hit Tim Westwood's show and showed just why they were the hottest new thing in hip-hop. And this was probably the first time anyone in the world heard Puff Daddy rap without that awful gruff growl he displayed on Supercat's “Dolly My Baby” remix.


While it's apparent that the threesome were rather intoxicated, the always colorful Biggie Smalls didn't disappoint—and surely offended a few people with his “I'm Jesus' Pops, Mary just blamed Joseph,” line, as well as complementing the Virgin Mary on her fellatio skills.

 

2. Eminem & Royce Da 5'9" "The 12 Minute Freestyle" (1998)

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Station: WKCR (89.9FM)

DJ: Stretch & Bobbito

Best Punchline: "Spit spectacular, crystal meth manufacturer/Stole your momma's Acura, wrecked and it sold back to her." (Eminem)



Back when aspiring rappers actually had to prove they had bars to gain acceptance in the hip-hop community (especially if said rapper was a white boy), Bad Meets Evil approached the scene with reckless abandon. For 12 unforgettable minutes on Stretch & Bobbito's airwaves, the new kids from Detroit proved that they could compete with even the greatest and most established rappers in the game.


Complex EIC Noah Callahan-Bever was in the studio for this freestyle (read about his wild and crazy experience here) and rumor has it that both Bad and Evil had indulged in a little bit of ecstasy before jumping on the mic.


With Em playing the comedic role: “Stole your Mama's Acura/Wrecked it and sold it back to her;” Royce was far more menacing, kicking threats like: “I got cats with bats you wouldn't play hardball with.” And if you think Game's a name dropper, Slim Shady called out more celebs than you could count on four hands.


It's just a shame it took upwards of twelve years for these two to rekindle their working relationship. But it was evident early on that they were poised to do big things.

1. Jay-Z & Big L "The 7 Minute Freestyle" (1995)

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Station: WKCR (89.9FM)

DJ: Stretch & Bobbito

Best Punchline: "Big L is the nigga you expect/To catch wreck, on any cassette deck/I'm so ahead of my time, my parents haven't met yet." (Big L)



On February 23, 1995, while out promoting his forthcoming debut, Lifestylez ov da Poor & Dangerous, Big L dropped by Stretch & Bobbito's show to play some joints from the album as well rock the mic. On this cold winter night, Lamont Coleman had a budding emcee by the name of Shawn Carter in tow, and they traded bars live on-air for almost ten minutes.


The two upstarts took turns riding Milkbone's “Keep It Real” instrumental, all while promoting their respective ventures. While L had a major label project hitting stores in a month, Jay hadn't yet secured a distribution deal for Roc-A-Fella, and was bragging about bagging the “Rap Pick Of The Week” on BET. Talk about humble beginnings!


It's hard to believe that Jay was once known as Big L's “man.” My how shit done changed. But while Jay is now touted as the greatest rapper of all time, on this night in 1995 he had trouble keeping up with the cool and confident Harlem emcee. Jay even ran out of breath at one point while L kept spitting punchlines galore.

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