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

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

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.”

57 Comments | Add a comment

  • [icon]

    B. October 6th, 2011 at 02:25 PM

    should've been number one...it was better than the Most Kingz and better than the big l freestyle

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    jowhite (@whitesaid) October 6th, 2011 at 02:50 PM

    Fact: Hov always gets too much shine around these parts. Fact: A list without Mad Skillz is suspect at best - how about the Supafriendz WKCR session from January '97 that I am referencing right here.

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    PER VERS October 6th, 2011 at 02:59 PM

    Please please PLEASE do not call the-greatest-ever-to-do-it (yeah I said it) "Big Daddy Kanye" LOL!

    • [icon]

      Complex October 6th, 2011 at 03:12 PM

      Fixed!

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    jonny October 6th, 2011 at 03:27 PM

    Why is Jay-z #1 always around here? he isnt 1/10 as good as complex makes it him out to be. I mean top 100 jay-z songs? he has like 4 good songs ever lmao. complex is a joke.

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      jimmy October 6th, 2011 at 03:32 PM

      you do know that lil wayne, nas, eminem, wu-tang have their own 100 song, right?

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      wtf October 11th, 2011 at 04:28 PM

      i feel you on that but this is number one niot because of jayz but for big l .... he slaurghterd this beat ... people dont even remeber this was milk bones beat .

  • [icon]

    cray October 6th, 2011 at 03:29 PM

    that gunit one mean

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    Cody Meltzer October 6th, 2011 at 03:31 PM

    Juice should totally be #1 he could beat anyone on this chart.

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    G-Ryder October 6th, 2011 at 03:37 PM

    you do kno that you uploaded the wrong Jadakiss freestyle at #33

  • [icon]

    slim October 6th, 2011 at 03:40 PM

    Juice- #36. Complex this list is fucked. J.U. should easy be #1, what a joke!

    • [icon]

      Cody October 6th, 2011 at 03:45 PM

      Slim you are 100% right! JUICE is #1

  • [icon]

    ABC October 6th, 2011 at 03:42 PM

    wrong jadakiss freestyle(#33),and the jayz grammy family freestyle is a Consequence & Kanye song, not Little Brother

    • [icon]

      Complex October 6th, 2011 at 03:57 PM

      Fixed. Thanks.

  • [icon]

    Hi. October 6th, 2011 at 04:47 PM

    ahh I thought the G-Unit On da Spot Freestyle would be on here...Banks carried them so bad. I actually expected a Banks freestyle on here in general.

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