I’ll follow Gordon’s example and try not to grab the low-hanging Malkovich fruit.
#1. In Back To School, Rodney Dangerfield plays a rich man who looks and sounds exactly like Rodney Dangerfield. He goes, titularly, back to school for various reasons, and uses his wealth to grease, fertilize, and make straight the way to his diploma. In one scene, he needs to write a paper about novelist and American treasure Kurt Vonnegut. So who better to write this paper than Vonnegut himself? Vonnegut is into getting some easy money, but Dangerfield’s teacher doesn’t agree with the quality of the finished paper. So it goes.
#2. In Don’t Think Twice, a troupe of improv comedians are soooo close to making it to fame and fortune. One of them has made it onto the cast of Pretty Much Saturday Night Live, and has to deal with his newfound success. Should he let his friends and troupe partners ride his coattails to stardom? Or are they dragging him down? Well, after his first show, the talented guy, who looks and sounds a lot like Keegan-Michael Key, introduces the guest host of Pretty Much Saturday Night Live to his friends at an afterparty. It’s Ben Stiller, star of print, TV, and the silver screen!
Imagine you were on the cusp of making it. Imagine you had imagined making it for years and years. Wouldn’t you imagine rubbing elbows with an international celebrity, perhaps someone who had made you laugh until you cried? Wouldn’t you imagine wanting to befriend him? Even if you hate his material, perhaps after he realized your wisdom, humor, and greatness, and he wanted to start hanging out with you, then you could ride his coattails to success! Even if you could make him laugh, that would be something to tell the grandkids about.
So these guys give Turning-Ben-Stiller-Into-A-Friend-And-Ally their best shot. It doesn’t go that well. But Ben Stiller isn’t a regular guy. I mean, he played Derek Zoolander. It takes a lot to impress him. With both fame and Ben Stiller’s friendship, they are found wanting.
#3. In Zoolander, rival male models keep building up beef until there is no resolution to their conflict except an underground winner-take-all catwalk walk-off. And who else could possibly judge a legendary walk-off besides a man of myth: the singular David Bowie.
Bowie was so weird and fascinating, he started to warp pop culture around himself. He shifted between so many personas, he began to assume a magical identity, as if he must have come from – not Mars, like Ziggy Stardust, but some other dimension of style and music. His film roles lead to increased splits in personality. He was a shapeshifting Goblin King. In The Prestige, he played that mad genius and possible fraud, Nikola Tesla. In Venture Bros., he led a worldwide crime league and could shapeshift into a bird (or so it seemed, for a few seasons). Here in real life, why wouldn’t he judge a goofy contest of the world’s most talented, beautiful, and vapid male models? And treat it with both seriousness and his own impeccable sense of style and style-making? Here, he’s treated like the king of the world that he created.
Christ, when Bowie passed away, they used this clip for the Oscars’ In Memoriam montage.
Here, he was playing the closest thing to himself that this world could contain.
Disqualified: I would have picked Lance Armstrong for his life-affirming, gumption-inducing cameo in Dodgeball, but he tested positive for performance-enhancing chemicals. :(
Now to listen to the podcast and see how many of these were already picked…