Who’s That Down in the Schoolyard? The Best Video Ever featuring Paul Simon, Spud Webb, Big Daddy Kane, and More!

This post is about a video that is so special, I can barely stand to write more words before embedding it. You can read my thoughts after stepping into the Internet’s finest time machine.

Prior to seeing this, I had always opined that 1988 was the best year ever, it being my birth year and the Year of the Dragon. After learning that, like me, the above video was also born in 1988, I can safely say that my fancy is indeed fact. I dare you to find an assembly of celebrities as eclectic and eccentric as the above company.

Paul Simon is perhaps the greatest folk-rocker of all time. After splitting up with Garfunkel in 1970, he recorded a self-titled album and the international hit seen above, “Me and Julio Down by the Schoolyard.” The song itself stands alone as a piece of art–even cooler is the debate that has spawned over the years regarding the song’s significance.

What’s not a debate is this video’s rank in the pantheon of music videos. Let’s break it down:

To start the video, Golden Age legends of hip-hop Biz Markie and Big Daddy Kane do their respective thangs by beat-boxing and rapping an intro.

“Ladies and gentlemen, check this out—a spectacular event in rhymin’/It might seem insane but the Big Daddy Kane is rockin’ the house with Paul Simon/And my man Biz Mark down in the park/even Spud Webb plays a cool part/in the video Me and Julio Down by the Schoolyard”

While Big Daddy Kane’s multitude of gold chains would make for a video themselves, the best stuff is after the rap–what follows is videographical splendor. Prior to the first athletic showdown, we see former dunk-champion Spud Webb doing his best Steve Urkel impression; meanwhile, Paul Simon couldn’t look more like Woody Harrelson in White Men Can’t Jump. They take the game seriously–Webb and Simon, remove their respective gear and put on a show that’s highlighted by Webb’s 360-degrees, one-handed alley-oop.

At the 2:14 mark, you might think to yourself, “Hey, this is great, but I didn’t watch this to break my personal jump-rope viewing record.” Fear not, viewer, because in this moment the late and great Mickey Mantle makes his appearance. Many of us never saw Mantle in action (nor did we see Paul Simon pitch a baseball)–luckily for us, Mantle leaves us with the image of a walk-off home run, which is fitting as he is MLB’s all-time leader in that category.

Thirty seconds later, the video features the most densely-packed game of football in schoolyard history, with at least 10 guys playing football in a space the size of my bedroom. Before anyone gets hurt, football icon John Madden comes out of nowhere to save the day. Summoning the boys, he beckons, “Hey guys, come here, come here. Hey, huddle up around here. I’ve been watching you guys, you guys need some fundamentals, you know what I mean? Knees bent, heads up…” Following this “heads up” phrase, the footballers tune him out and go back to playing as Madden rambles incoherent gibberish, a pattern eerily similar to the dynamic between Madden and his television viewers.

The masterpiece concludes with Simon walking past a Graffiti-laden wall holding a massive 80’s style boom-box.

This video is interesting because it takes so many seemingly disparate figures in society and pieces them together like vegetables in a stew. (Forgive me, I know that’s a bad analogy, but I’m hungry.) But seriously, it’s interesting how prolific figures such as Madden, Mantle, and Simon end up in the same video as Spud Webb. Perhaps this is a window into how people in 1988 viewed Spud Webb, high in the sky among the world’s basketball elite.

I wouldn’t have the video any other way.

Who’s your favorite cameo? Do Spud’s slams impress? Comment on the article or email us at AGRbasketball (at) gmail.com. Don’t forget to follow @AGRbasketball on twitter and to like us on Facebook!