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The 50 Best Radio Freestyles

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

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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