These Celebrities Had Super Awkward Encounters With Donald Trump

Before his presidency, Donald Trump was involved in the entertainment industry. He has a star on the Hollywood Walk of Fame, after all. As a result, many Hollywood stars have stories about meeting the goofy TV personality who would soon lead the nation.

Many of these stories paint a picture of Trump as someone you would not expect to ascend to the highest office. These are the most awkward stories of stars encountering Trump before he became president. You won’t believe which supermodel turned down his request for a date (page 9).

1. George Clooney got mocked on national television

George Clooney in 2015

Oscar-winning actor George Clooney | Neilson Barnard/Getty Images

George Clooney says he met Trump once about 10 years ago. Clooney was out to dinner, and Trump approached him. They talked for a little while; Trump told Clooney he’d recommend a doctor to deal with his neck issue. That was the end of it.

But then Trump went on Larry King Live and made fun of Clooney’s height, telling King that Clooney is “very little.” Clooney had thick skin though, saying Trump’s comment “made me laugh.”

Next: Trump completely faked this star’s wedding gift.

2. Charlie Sheen received fake platinum cufflinks as a wedding gift

Actor Charlie Sheen attends a movie premiere.

Charlie Sheen attends a movie premiere. | Michael Buckner/Getty Images

During the 2016 election, Charlie Sheen said he wasn’t a fan of Donald Trump.

As Sheen explained on The Graham Norton Show, he was at dinner one night when Trump approached him, saying he wanted to give Sheen a wedding gift (even though Trump wasn’t invited to his wedding). Trump then took off the cufflinks he was wearing, which he said were platinum diamond Harry Winston, and gave them to Sheen.

About six months later, Sheen got some jewelry appraised, and he found out the cufflinks were fake. “And I just thought, ‘What does this really say about the man?'” Sheen asked.

Next: Trump goes head-to-head with a fellow billionaire.

3. Mark Cuban dealt with condescending comments

Andrew Ross Sorkin and Mark Cuban speak onstage

Mark Cuban | Michael Cohen/Getty Images

In 2004, businessman Mark Cuban shared the story of how he met Trump for the first time at a party in 1999. Trump told Cuban that “someday, maybe we could sit up there with the rich people,” looking up at the second-floor patio. Cuban was already doing fairly well for himself back then, being the co-founder of a company,, with $13 million in revenue (and Yahoo would soon buy it for almost $6 billion).

Cuban says he later took a meeting with Trump at Trump Tower, and he was shocked that virtually every inch of Trump’s office was covered in pictures of himself. He says this left a lasting impression.

“After leaving your office, I promised myself that if I ever got liquid and had an obscene amount of money in the bank, I would make a point not to remind myself and everyone else around me of it every minute of every day unlike you,” Cuban said.

Next: Trump gives odd advice to a young star.

4. Daniel Radcliffe got really weird advice

Daniel Radcliffe

A young Daniel Radcliffe met Trump during his first media interview. | Stuart C. Wilson/Getty Images

Daniel Radcliffe says when he was 11 years old, he was getting ready to go on Today. While he was there, he met Trump, telling the businessman he was nervous and not sure what he would say on the show. Trump responded, “You just tell them you met Mr. Trump.”

Recalling the story on Late Night with Seth Meyers, Radcliffe said he can’t relate to this level of confidence.

Next: This encounter proves Trump should avoid parties.

5. Richard Dreyfuss ranted about Trump’s party behavior

 Actor Richard Dreyfuss arrives at American Film Institute's 45th Life Achievement Award Gala Tribute to Diane Keaton

Richard Dreyfuss | Kevin Winter/Getty Images

Back in May 2016, Richard Dreyfuss ranted about Trump on Twitter, saying Trump’s celebrity endorsers are “whores” and calling Trump an “unqualified racist.” Then he shared a story of meeting him.

At a party in Malibu, Trump “got very upset that his date had the [gall] to speak with other guests. He acted like a small d*cked prick and pusher from the party and left of us wondering if we had made a mistake [letting] her go with him.” Dreyfuss has since deleted these tweets.

Next: A Saturday Night Live afterparty was anything but funny for this celebrity.

6. Jon Hamm faced off with him at a SNL party

Jon Hamm attends the "Mad Men" New York Special Screening at The Museum of Modern Art

Jon Hamm | Dave Kotinsky/Getty Images

In November 2015, Trump hosted Saturday Night Live, and Jon Hamm ran into him at the show’s afterparty. Hamm told The New York Times that Trump and Bill O’Reilly tried to intimidate him with their height:

They’re both tall dudes. And I’m a tall dude. And they both do that tall-dude thing, which is try to intimidate you. And it doesn’t work on me. I’m like, “I’m as alpha as you. Let’s go. You’re not going to chest-bump me.” It was a very weird night. It was the shortest I’ve ever stayed at an S.N.L. after-party.

Next: This celebrity says Trump hit on his wife at a party. 

7. Billy Baldwin says Trump hit on his wife

In November 2017, Donald Trump Jr. tweeted about multiple women accusing Senator Al Franken of sexual harassment. This struck some as hypocritical, since the president has been accused of sexual harassment and assault, too. So Billy Baldwin responded to Trump Jr.’s tweet with a story.

Trump owned the Plaza Hotel, where Baldwin was throwing a party. He says Trump showed up uninvited and hit on his wife, inviting her to fly on his helicopter to Atlantic City. Of course, Baldwin says his wife rejected Trump. He also said Trump is “a 5th degree black belt when it comes to sexual impropriety allegations.”

Next: Not even British royalty could escape Trump’s advances.

8. Princess Diana reportedly got the creeps

Princess Diana | Torsten Blackwood/AFP/Getty Images

Yes, President Trump supposedly hit on Princess Diana, shortly after her divorce from Prince Charles. Diana never told the story publicly, but journalist Selina Scott made this allegation in The Sunday Times.

Scott says she was working on a documentary about Trump in 1994, and she personally witnessed Trump bombard Diana with bouquets of flowers and handwritten notes after her divorce. This was after Trump privately said Diana seemed like “a handful.”

Scott says that at a dinner, Princess Diana told her about the flowers, saying, “What am I going to do? He gives me the creeps.” Years later, Howard Stern interviewed Trump, who bragged he could have had sex with Diana.

Next: “America’s richest man” used a weird pickup line on this model.

9. Brooke Shields says Trump asked her on a date

Brooke Shields

Brooke Shields | Dave Kotinsky/Getty Images

Model and actress Brooke Shields told The LA Times that Trump asked her out on a date in the ’90s, after Trump’s divorce from his first wife, Ivana. Trump evidently called Shields and said, “I really think we should date because you’re America’s sweetheart and I’m America’s richest man and the people would love it.”

Shields said no because she had a boyfriend at the time. But considering the disgusted look on her face while telling the story on Watch What Happens Live, it’s clear she wouldn’t have said yes either way.

Next: The president wouldn’t take no for an answer with this actress.

10. Salma Hayek says Trump used her boyfriend to get a date with her

Salma Hayek attends the 2003 Academy Awards.

Actress Salma Hayek was not impressed by Trump’s advances. | Kevin Winter/Getty Images

Another example of Trump attempting to woo a famous celebrity, Salma Hayek says Trump tried to date her. As she explained on The Daily Show with Trevor Noah, she was at an event and got cold, so Trump came over and put his coat on her. Then he turned to Hayek’s boyfriend and said, “I’m sorry, your girlfriend, I saw she was cold.”

Hayek says Trump befriended her boyfriend and then invited them to dinner. The boyfriend brought Hayek and Trump got both of their numbers, but he never called the boyfriend. It became clear to Hayek that this was just a way of getting her number.

She says Trump subsequently called and invited her — just her — to an event. When Hayek reminded him that she has a boyfriend, Trump apparently said, “He’s not good enough for you.”

Next: This comedian tried and failed to get a photo with Trump. 

11. Norm MacDonald’s request got rejected

Comedian Norm MacDonald

Comedian Norm MacDonald wasn’t joking about his request. | Jason Kempin/iStock/Getty Images

Comedian Norm MacDonald says he once met Trump while they were both on a talk show. This was during the presidential election, so the Secret Service surrounded Trump.

During the few minutes between acts, MacDonald asked Trump for a picture. He replied, “Ah, you’re funny. I love ‘ya. I’ll take a picture with you in a minute.” Then Trump turned around, got in an elevator, and never came back.

Next: This celebrity met Trump while goofing on him for his TV show.

12. Sasha Baron Cohen became ‘the first person to dislike Trump’

 Sasha Baron Cohen

Posing as “Ali G,” Sasha Baron Cohen tricked Donald Trump. | Getty Images

Sasha Baron Cohen has the distinct honor of disliking Trump before everyone else. The actor interviewed the billionaire in 2003 for Da Ali G Show, which involved Cohen interviewing people as Ali G, making them think Ali G was an actual person and not an act.

So in 2003, Cohen interviewed Trump as Ali G and tried to sell him a business idea, but Trump didn’t go for it. Trump later walked out of the interview, supposedly realizing it was a joke. The billionaire later tweeted that he walked out “immediately,” proving he doesn’t fall for scams.

On The Late Late Show, Cohen joked he was the “first person, actually, to realize that he’s a d*ck.” The Borat star also said Trump hardly realized it was a joke. “He claims that he saw through the interview,” said Cohen. “But actually, he was there for about seven minutes.”

Next: This celebrity met Trump while wearing an elf costume.

13. Aubrey Plaza wore an elf costume to meet Trump

Aubrey Plaza attends a gala.

Actress Aubrey Plaza is known for her antics. | JC Olivera/Getty Images for National Hispanic Media Coalition

Aubrey Plaza of Parks & Recreation fame has a unique story of meeting the future president. As she explained on The Late Show with Stephen Colbert, when she was 20, she lived in New York and worked as a mascot of the British children’s character Noddy.

One day, Plaza had a job at FAO Schwarz. Her boss told her she must get a picture with Trump that night or he would fire her. So Plaza tried get a photo, but Trump didn’t want it. “He kept shooing me away,” Plaza said. “I kept dancing over to him trying to get the picture, and I finally just kind of put my creepy elf arm around him and forced him in there and got that picture.”

Plaza joked if she knew then what she knows now, she would have tackled him to the ground.

Next: This celebrity met Trump when the future president made a cameo on his sitcom.

14. Peter Marc Jacobson says Trump had a hilarious request when appearing on The Nanny

Peter Marc Jacobson

Peter Marc Jacobson | Jason Merritt/Getty Images

Trump made cameo appearances in dozens of films and TV shows from the late 1980s into the 2000s. One of those was on the sitcom, The Nanny, in which Trump plays himself and is depicted as a highly important person who the main character runs into after her status is elevated.

When Trump started running for president, these cameos began earning new attention, and Peter Marc Jacobson, the co-creator of The Nanny, recalled meeting Trump for this cameo. He told Newsweek that Trump demanded a line be changed in the script. Jacobson explained:

We sent the script to Mr. Trump, and in return I got a message from casting that said, “Mr. Trump has a problem with the line above: ‘Do all you handsome millionaires know each other?'” I was actually impressed and thought, “Isn’t it nice that he’s humble and doesn’t want to call himself a millionaire?” Then I read the rest of the note, and it said, “Since he’s a billionaire, he would like the line changed accordingly.”

NextThis celebrity did the walk of shame in front of Trump. 

15. Bethenny Frankel runs into Trump after a night out

Bethenny Frankel in a black and white dress

It takes a lot to embarrass reality star Bethenny Frankel | Slaven Vlasic/Getty Images

Bethenny Frankel says she had an awkward run-in with Trump, though it wasn’t because of anything Trump did. She explained that she ran into the future president at 7:45 a.m. after sleeping over with a date. Much to her chagrin, Trump recognized her and said hello.

“He gave me a hug, and I was like, ‘Oh my God, I probably have the worst Skinny Girl alcohol breath,’” Frankel said. “It was the walk of shame! I might have done the walk of shame with the future president.”

Read more: The Most Fascinating Things You Never Knew About Donald Trump’s Childhood

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