1. SEE, HEAR: Paul Simon ft. Biz Markie & Big Daddy Kane — “Me and Julio Down By The Schoolyard” Music Video (1988).

    This Paul Simon video takes place on a NYC playground. (P arrives carrying a ghetto-blaster, walking past ’80s style graffiti.) That in itself might not get you hype. Seeing Big Daddy Kane rap a little intro while Biz Markie beatboxes might though. If that ain’t enough for you, then Paul assisting a slam-dunking Spud Webb on the basketball court like he was John Stockton or striking out givin’ up a homer to Mickey Mantle in a friendly game of stickball might do the trick. (Look for football coach/analyst/video game icon John Madden at the end.)

    UPDATE: Shout outs to Large Professor , who informed us that this was the first video he ever appeared in. He’s wearing the yellow tank top in the Madden scene.

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