10 Of Donald Trump’s Goofiest Pop Culture Moments

Saturday Night Live has been mocking Donald Trump since the late ‘80s. So, you’d assume that he’d want to keep his distance from the NBC sketch show. However, in 2004, when hype for The Apprentice was at an all time high, Trump was invited to host the show. He appeared in awkward sketches opposite Amy Poehler, Jimmy Fallon, and Seth Meyers, but he also had to face down the guy who delivered the most devastating impression of him: Darrell Hammond. This Regis and Kelly Live sketch could have been a way for Trump to outshine Hammond, but a young Amy Poehler steals the spotlight.

We’re not quite sure whose idea this was, but Rudy Giuliani once dressed up in drag and the Trumpster kissed and fondled the former New York City mayor. The sketch was filmed for The Mayor’s Inner Circle Press Roast in 2000 and is included in the documentary Giulianitime. So, I guess Giuliani thought it was a lark, and Trump was totally game? I GUESS???

Donald Trump has wiggled his way into countless movies, but his first onscreen appearance was in the 1990 monstrosity Ghosts Can’t Do It. Trump plays a businessman in the John Derek flick which is all about his IRL wife Bo Derek struggling to rebuild her life after the death of her husband played in the movie by Anthony Quinn. If that’s not weird enough, John Derek died before the film came out. Oh, and Quinn can speak to Bo Derek as a ghost. Nathan Rabin has an in-depth rundown of the film over at Splitsider if you want to understand more about the context of the scene. But, uh, really, I don’t know if you can ever truly understand the full context of the scene. It’s that…weird.

Hey! Remember how during the Republican primary debates Trump said that Rosie O’Donnell was the only woman he had ever disrespected? The two media figures have enjoyed a very public feud over the last few decades that escalated about ten years ago. What was the cause of this acrimony? Well, before all of our pop culture feuds played out on social media, they played out on Entertainment Tonight. Trump went on the peppy celebrity news magazine and explained in full detail all the reasons he hated her. Mostly, they boil down to the fact that she’s unattractive.

There are two ways to look at Trump’s involvement in The Apprentice. On the one hand, it was an extraordinarily savvy business move to produce and star in an entertaining show. On the other, he became an even bigger caricature of himself. Between the catchphrases and the cat fights, Trump established himself as one of the first big reality TV stars. The label brings with it tons of fame and money, and a tawdry reputation. Still, Trump was so successful because he was able to fully unleash his inner showman. Take for instance, the episode where he fired not one, not two, not three, but four people at the same time. That’s cruel, but that’s also entertainment.

The Friars Club roasts began as a way for elite members of the illustrious private club to honor each other by ripping each other apart. Comedy Central aired a few of them, and then when their contract expired, started making their own. In 2011, their target was The Donald. Trump allowed himself to be mocked by Seth MacFarlane, Whitney Cummings, Lisa Lampanelli, Larry King, and The Situation. So, yeah, I’m sure he can handle whatever a Chinese ambassador would throw at him. You can buy the bawdy special on VOD here on Amazon Instant Video.

We all know that Donald Trump is a fan of money, but he might be an even bigger fan of WWE wrestling. Trump has sponsored numerous events over the years and even gotten in on the action. In 2007, he and pal Vince McMahon squared off against each other in something called “The Battle of the Billionaires.” No, they didn’t get in the ring, but they did make other people get in the ring on their behest. The stakes, though, were sort of high for them. Whoever’s man lost would have to get his head shaved by the other. Naturally, McMahon didn’t get his paws on Trump’s flaxen locks.

That’s not all Trump did to McMahon, though… In 2009, he “bought” WWE Raw and appeared on screen taunting McMahon. The next week, McMahon “bought” it back for twice the amount. So, we’re pretty sure it was scripted. It was scripted, right? Is wrestling scripted?

[youtube https://www.youtube.com/watch?v=6JFXSnfb5fw]

Above all things, Donald Trump is a consummate business man and he knows how to sell us on a deal. So, it’s ironic that his most compelling business pitch was a big, fat, hilarious fake. Remember when he hosted Saturday Night Live? Well, the funniest sketch of the night was one called “Donald Trump’s House of Wings.” It’s a faux commercial wherein Trump promotes his new restaurant with the help of some intense chicks. Unfortunately, the clip is hard to legally find because of copyright usage laws relating to the use of that catchy Pointer Sisters song, but we tracked down this bootleg. It’s grainy, but well-worth watching.

Even though this list is dedicated to Trump’s hugest, funniest, wackiest moments on screen, we would be remiss if we did not include one of the few documentaries about the man. However, this is not a fluff piece. You’ve Been Trumped follows what happens when he decides to build a luxury golf course in the Scottish countryside. The problem? The locals aren’t too happy about having their land and homes destroyed in the process. You can buy or rent it on VOD and it’s free to stream for people with a SundanceNow Doc Club membership. [Where to Stream You’ve Been Trumped]

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