Before his presidential campaign, Donald Trump has been involved in a lot of random endeavors.

Donald Trump. Love him or hate him, he is undeniably an American icon.

As the current leader of the Republican presidential race, Trump’s name is more recognizable now than ever before. With his newfound political success, many people were quick to forget the bloated and pompous, yet charming and entertaining celebrity that he was before he began his campaign.

While Trump has always been famous for being a successful businessman, he’s also made a name for himself by doing some pretty wacky things over the years, ranging from professional wrestling to reality TV shows.

Here are some of Trump’s “unconventional” endeavors from years past to remind you what made the eccentric billionaire so entertaining in the first place.

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Trump the Wrestler

The Donald entered the wrestling ring in 2007, as part of Wrestlemania 23’s “Battle of the Billionaires” storyline, which pitted Trump against fellow billionaire and WWE owner, Vince McMahon.

During the match, Trump memorably tackled McMahon to the ground, while Trump’s wrestler, Bobby Lashley, defeated McMahon’s wrestler, Umaga. As part of the storyline, Trump and Lashley also got to shave McMahon’s head on national television after the match was over.

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Trump the Roastee

In 2011, Trump was the guest of honor on his very own Comedy Central Roast. Featured at the event was a slew of celebrities and comedians, including Seth MacFarlane, Snoop Dogg, Lisa Lampanelli and even Larry King. Over the course of the evening, violent jabs were taken at Trump’s hair, his numerous wives and his blunders in the casino business. The line of the night, however belonged to Trump himself, during his rebuttal.

“What’s the difference between a wet racoon and Donald J. Trump’s hair? A wet raccoon doesn’t have seven billion f--kin’ dollars in the bank.”

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Trump the Salesman

The Trump Organization is primarily composed of luxury hotels and golf courses around the world, but Donald Trump has slapped his name on various other products over the years. Trump Vodka, Trump Steaks, Trump Chocolate, Trump Ice bottled water, Trump The Game and even Donald Trump The Fragrance For Men were all, at some point, legitimate products.  

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Trump the Owner

Believe it or not, Donald Trump, at one point, actually owned a professional sports team.  Well, a semi-professional sports team.

In 1983, Donald Trump purchased the New Jersey Generals, a football team playing in the now-defunct United States Football League. According to ESPN, Trump attempted to hire legendary Miami Dolphins coach Don Shula to coach the Generals, but the deal never materialized after Shula demanded to have his own apartment in Trump Tower as part of the contract.

The USFL later folded in 1986 due to increased competition in the NFL, and Trump’s ownership faded into obscurity.

Trump the Reality Star

Donald Trump’s reality show, The Apprentice, premiered in 2004 and brought the business magnate to the silver screen. On the show, businessmen and businesswomen competed in tasks for the opportunity to be hired by The Donald and join the Trump Organization. At the end of each episode, Trump would deliver his famous catchphrase to one unlucky competitor: “You’re fired."

The show was an immediate hit and ran for six seasons, before transitioning into a new format, The Celebrity Apprentice, where celebrities would compete to earn money for charity. Among the memorable celebrities appearing on the show were Piers Morgan, Joan Rivers, Dennis Rodman and Lil Jon.

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Trump the Screen Star

Aside from appearing in his own show, Donald Trump has also guest starred in a number of famous TV shows. Some of his more notable appearances include The Fresh Prince of Bel-Air, The Nanny and Days of Our Lives. He also had a big screen cameo in Home Alone 2: Lost in New York, in which he encountered Kevin McCallister in the lobby of the Plaza Hotel.

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Trump the Comedian

Donald Trump’s celebrity status has elicited many parodies on Saturday Night Live, but he has also hosted the show twice, in 2004 and in 2015. The 2004 episode made light of Trump’s ventures as a businessman and The Apprentice, while the 2015 episode focused on his presidential campaign. Despite all of the hilarious political gags in the 2015 episode, perhaps the funniest moment occurred when The Donald showed off his dance moves in a sketch parodying the music video for Drake’s “Hotline Bling.”

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Trump the Pageant Host

It’s no secret that Donald Trump loves supermodels, and in 1996, he acquired the world’s largest and most viewed beauty pageant, the Miss Universe Pageant. Trump and NBC worked jointly to operate the event for nearly 20 years, until NBC dumped him in 2015 after his controversial comments about illegal immigration.


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