Many Hollywood stars met Donald Trump during his time in the entertainment industry. And they often walked away with bizarre stories of the future world leader. These are the most awkward celeb encounters with Trump, who called one famous actor “very little” on national TV (see page 9).
1. Christie Brinkley
- The supermodel called Trump “smarmy” after getting to know him.
In early 2018, Christie Brinkley revealed POTUS invited her on his private jet because they were both traveling to Aspen, Colorado. At the time she was dating Billy Joel and Trump was married to his first wife, Ivana. The supermodel declined, but Trump doubled down, telling Brinkley to cancel her flight and travel with him. The supermodel explained, “I knew he was married, and there he was asking me to go on his plane. He was kind of flirty about it. He was out chasing skirts.”
Brinkley added that she dined with him before, too. “I’ve always found him smarmy, as in, ‘’Watch out, part the waves, the rich people are coming.'”
Next: Trump hit up this recent divorcee.
2. Emma Thompson
- Trump asked Emma Thompson to stay in Trump Tower.
In 1998, a recently divorced Thompson received a cringe-worthy call from Trump, asking her to stay at one of his properties. The actress had never met him before, telling a Swedish show he said, “I just wondered if I could offer you some accommodation in one of my Trump Towers. They’re really comfortable.” Thompson asked for clarification, and he explained, “Well, I think we would get along very well — maybe have dinner sometime.” The actress said she’d call him back, but never did.
Next: Trump gives odd advice to a magical, young star.
3. Daniel Radcliffe
- Trump gave Daniel Radcliffe weird advice about his nerves.
When he was 11 years old, Radcliffe was preparing to go on Today. While he was there, he met Trump, telling the businessman he was nervous and not sure what he’d say on TV. Trump responded, “You just tell them you met Mr. Trump.” Recalling the story to host Seth Myers, Radcliffe said he can’t relate to this level of confidence.
Next: Not even British royalty could escape Trump’s advances.
4. Princess Diana
- Trump gave Princess Diana the creeps.
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 witnessed Trump bombard Diana with bouquets of flowers and handwritten notes. 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.
5. Brooke Shields
- Trump asked Brooke Shields on a date using a weird pickup line.
The model told The LA Times Trump asked her out on a date in the ’90s, after Trump’s divorce from his first wife, Ivana. He 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. But considering the 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: Trump knew too much about this Microsoft magnate’s offspring.
6. Bill Gates
- Trump knew little about vaccines but a lot about Bill Gates’ daughter.
Gates spoke with Trump twice after the election, and both meetings concerned the Microsoft co-founder, according to Bloomberg. First, Trump asked him the difference between HIV and HPV while discussing vaccines. So Gates explained with amusement, “Those are rarely confused with each other.”
Second, Gates was alarmed when Trump brought up his daughter Jennifer, a successful equestrian who met the future president at a horse show. “When I first talked to him it was actually kind of scary how much he knew about my daughter’s appearance,” Gates said.
Next: A blind date gone wrong for Trump
7. Candice Bergen
- Candice Bergen was set up on a blind date with Trump in the ’70s.
“He was wearing a three-piece burgundy suit and burgundy patent leather loafers in a burgundy limousine,” the former model laughingly told Andy Cohen in 2017. “He was a good-looking guy, and a douche.” Bergen explained she left the date early and made no physical contact with the future president. She did not appreciate the date setup.
Next: This chilled actress accepted Trump’s jacket.
8. Salma Hayek
- Trump used Salma Hayek’s boyfriend to try to date her.
As Hayek explained on The Daily Show with Trevor Noah, she was at an event and got cold, so Trump put his coat on her. Then he said to Hayek’s boyfriend, “I’m sorry, your girlfriend, I saw she was cold.” Hayek says Trump befriended her boyfriend and invited them to dinner. The boyfriend brought Hayek, and Trump got their numbers, but he never called the boyfriend.
She says Trump subsequently called and invited her — just her — to an event. When Hayek reminded him of her boyfriend, Trump reportedly said, “He’s not good enough for you.”
Next: Trump called this big-time actor “very little” in stature.
9. George Clooney
- Trump mocked George Clooney’s height on national television.
Clooney says he met Trump about 10 years ago. Trump approached the actor while he was out to dinner. They talked for a bit; Trump told Clooney he’d recommend a doctor to deal with his neck issue. That was the end of their conversation. But Trump went on Larry King Live and made fun of Clooney’s height, saying he’s “very little.” The actor had thick skin though, saying Trump’s comment “made me laugh.”
Next: This celebrity met Trump while wearing an elf costume.
10. Aubrey Plaza
- Aubrey Plaza was dressed as an elf when she met Trump.
Parks & Recreation actress Aubrey Plaza explained 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 to get a picture with Trump or he’d fire her. So Plaza tried, but Trump didn’t want it.
“He kept shooing me away,” Plaza said. “… 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: Trump goes head-to-head with a fellow billionaire.
11. Mark Cuban
- Entrepreneur Mark Cuban was shocked by Trump’s ego.
In 2004, Cuban shared the story of how he met Trump at a party in 1999. Trump told Cuban, “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 as the co-founder of Broadcast.com.
Cuban says he later met with Trump at Trump Tower and was shocked that his office was covered in pictures of himself. “After leaving your office, I promised myself that if I ever … 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 completely faked this star’s wedding gift.
12. Charlie Sheen
- Charlie Sheen received fake platinum cufflinks from Trump.
While out to dinner, Trump approached Sheen and wanted to give him a wedding gift (Trump wasn’t invited to his wedding). The future president took off his cufflinks, saying they were platinum diamond Harry Winston, and gave them to Sheen. About six months later, Sheen got some jewelry appraised and discovered the cufflinks were fake. “And I just thought, ‘What does this really say about the man?'” Sheen asked.
Next: A Saturday Night Live afterparty was anything but funny.
13. Jon Hamm
- Both Trump and Bill O’Reilly tried to intimidate Jon Hamm.
In November 2015, Trump hosted Saturday Night Live, and Hamm ran into him and O’Reilly at the show’s afterparty. Hamm told The New York Times:
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.
14. Billy Baldwin says Trump hit on his wife
- Trump hit on Billy Baldwin’s wife at a party.
In 2017, Donald Trump Jr. tweeted about several women accusing Senator Al Franken of sexual harassment. This struck some as hypocritical, since his father has been accused of sexual harassment, too. So Billy Baldwin responded to Trump Jr.’s tweet with a story.
Trump owned the Plaza Hotel, where Baldwin threw a party. He says Trump showed up uninvited and hit on his wife, inviting her to take his helicopter to Atlantic City. Of course, Baldwin said his wife rejected him and that Trump is “a 5th degree black belt when it comes to sexual impropriety allegations.”
Next: This comedian tried and failed to get a photo with Trump.
15. Norm MacDonald
- Trump rejected Norm MacDonald’s request for a photo.
Comedian Norm MacDonald says he met Trump on a talk show. This was during the presidential election, so Secret Service surrounded the future president. During a 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 encounter proves Trump should avoid parties.
16. Richard Dreyfuss
- Richard Dreyfuss lost it on Trump in a Twitter rant.
Back in May 2016, Dreyfuss ranted on Twitter, saying Trump’s celeb endorsers are “whores” and calling him an “unqualified racist.” Then he shared a story. At a party in Malibu, Trump got “upset that his date had the [gall] to speak with other guests. He acted like a small d*cked prick and pushed her 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: This celebrity met Trump while goofing on him for his TV show.
17. Sasha Baron Cohen
- Sasha Baron Cohen disliked Trump before everyone else.
The actor interviewed the billionaire in 2003 for Da Ali G Show. Cohen posed as Ali G, making them think he 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 he walked out “immediately,” proving he doesn’t fall for scams.
I never fall for scams. I am the only person who immediately walked out of my ‘Ali G’ interview
— Donald J. Trump (@realDonaldTrump) October 30, 2012
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 when the future president made a cameo on his sitcom.
18. Peter Marc Jacobson says Trump had a hilarious request on The Nanny
- Trump demanded a script change to clarify he’s a billionaire.
Trump made cameos in dozens of films and TV shows from the late ’80s into the 2000s. On one sitcom, The Nanny, Trump plays himself and is depicted as an important person the main character meets after her status is elevated. Peter Marc Jacobson, The Nanny co-creator, recalled 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.”
Next: This celebrity did the walk of shame in front of Trump.
19. Bethenny Frankel runs into Trump after a night out
- Bethenny Frankel ran into Trump after a sleepover.
Frankel says she had an awkward run-in with Trump — but not because of anything he did. She explained she ran into the future president at 7:45 a.m. after sleeping over with a date. And 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. “I might have done the walk of shame with the future president.”
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