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.