Top 10 Crazy Donald Trump Moments

This guy is "yuge!", and he's also had his share of crazy moments over the years. Whether it's getting into a media battle with Rosie O'Donnell or hosting his own reality show, there's never any shortage of strange moments with "The Donald". Join WatchMojo.com as we count down ten of Donald Trump's craziest moments.
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Top 10 Crazy Donald Trump Moments


This guy is “yuge!” Welcome to WatchMojo.com, and today we’ll be counting down our top 10 favorite Donald Trump moments.

#10 – Trump: The Brand

Donald Trump is a businessman, real-estate developer and mogul. But more than that, he is a brand. And that brand is larger-than-life. The Donald has brought his gold touch to a lot of different products. Our fave? Not the books, the buildings or the booze – it’s the board game. Whether it’s vodka, an airline, hotels or casinos, if it’s Trump you can be sure it’s tacky.

#9 – A Rosie by Any Other Name Is Just As Degenerate

Trump is not the nicest kid on the playground. To be fair, Rosie started this feud: in 2006, after The Donald decided not to strip Miss USA of her crown when she was caught underage drinking, O’Donnell criticized his ethical judgment. It all went downhill from there. Did they bury the hatchet? Nope! But he did wish her well after her heart attack in 2012, so give him some credit.

#8 – The Donald Gives Vince McMahon a Haircut

We know it’s a yuge shock that a class act like Trump is a wrestling fan and friends with Vince McMahon. Donnie has even been involved in some WWE storylines, one of which resulted in this. Should Trump really be allowed to style other people’s hair? Seriously though: how much would you pay to see Trump shaved bald???

#7 – Rudy and Donald Sitting in a Tree…

At one point or another, both Rudy Giuliani and Donald Trump were legitimately possibly going to run for President. That’s this Rudy Giuliani and Donald Trump. Sorry we should have warned you first – you cannot un-see this! We don’t even know what the message of this video is supposed to be. But we do think they make a cute couple.

#6 – You’re Fired

You gotta give it to The Donald: he’s great at finding strange new ways to feed his ego. One of his most successful is “The Apprentice.” The premise is pure Trump: he tells people what to do, how to do it and has them battle for his approval. He even got a catchphrase. And became one of TV’s highest paid stars.

#5 – Par for the Course

A big shot American businessman purchases a pristine chunk of Scottish countryside to build, build, build. Is this the plot of a movie? Well, yes. But it was also the plot that unraveled in at the hands of The Donald, as told by the documentary “You’ve Been Trumped.” However, instead of coming to love the area’s regional charm and changing his plans like his movie counterpart, Trump bullied, bulldozed and built his golf course.

#4 – Trump Gives Birther to Some Strange Ideas

Trump isn’t a Barack Obama fan. He proved that by demanding to see Obama’s birth certificate – y’know, ‘cause there’s no way he was born in America. Whether it was a political dispute, latent racism, or just plain stupidity, we can’t say. But when he then tries to blackmail the President into releasing his school records via a super-duper-yuge-ginormous announcement; well, that’s the last straw.

#3 – Would He Paint the White House Gold?

Wasn’t it easier when Donald Trump was only famous for making money and getting divorced? Somewhere along the way, Trump went from an eccentric businessman with a quirky hairdo to a right-leaning political force with a really quirky hairdo. While he’s donated to candidates in both parties, Trump threw his toupee into the ring in 2011 as a potential Republican Party nominee. That did make for some great soundbites about him, and jokes about him, but he dropped out pretty fast. Although he did explain what he’d bring to the table as President.

#2 – All A-Twitter After Election Results

While Americans celebrated Obama’s reelection, Trump was quietly sulking. Did we say quietly? We meant obnoxiously posting a barrage of hateful tweets. Actually, let’s open this up to anything Trump has ever said on Twitter, ever. What does he use his 140 characters for? Feuding with respected newsmen, quoting himself, bragging like it’s going outta style – which it is btw – and name-calling. You stay classy, Donald Trump.

#1 – Trump Can Take a Joke

Say what you will about the man, but he can take it as well as dish it out. And as we’ve seen, he can definitely dish it out. President Obama has gotten a few jabs in at The Donald’s expense. But the best was when he sat through an entire roast where he was mocked without mercy. But, as always, The Donald had the last laugh.

What are your favorite Donald Trump moments? For more entertaining trivia videos, be sure to subscribe to WatchMojo.com.
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