12 Celebrities Who Have Publicly Sparred With Donald Trump: Robert De Niro, Meryl Streep and More

Both Donald Trump and his wife, Melania Trump, had constantly feuded with Anna Wintour after Vogue endorsed 2016 Democratic opponent Hillary Clinton. The Mirror also reported that the editor-in-chief discussed the controversy surrounding the Donald J. Trump Foundation, saying it had done "nothing."

"Its board is packed with relatives, and he’s going to use his presidency to sell himself and his brand and profit personally for himself and his family," Anna reportedly said.

She apologized afterward and wished Donald success in his political journey, but months later, she announced she would never invite the ex-POTUS to the Met Gala again.

In 2017, Vanity Fair came under fire for sharing a video that made fun of Hillary's supporters. The outlet issued an apology afterward, but Donald saw it as a chance to lambast Anna.

"Vanity Fair, which looks like it is on its last legs, is bending over backwards in apologizing for the minor hit they took at Crooked H," said Donald. "Anna Wintour, who was all set to be Amb to Court of St James's & a big fundraiser for CH, is beside herself in grief & begging for forgiveness!"

During his 2013 appearance on The Tonight Show with Jay Leno, Bill Maher ignited a feud with Donald when he joked that the presidential candidate was the spawn of an orangutan and that he would donate $5 million to charity if the businessman could prove his father was not a great ape.

In response to the statement, Donald filed a $5 million lawsuit against Bill for failing to donate the money after sharing his birth certificate.

After more exchanges in the years thereafter, Donald lashed out at the comedian and his Real Time show.

"Bill Maher, the highly overrated ‘Star’ of the ratings-challenged show with the Fake, Loud and Obnoxious laughter pouring out of your set every few seconds, even when nothing was said that was funny (which is most of the time!), suffers from a terminal case of Trump Derangement Syndrome, sometimes referred to as TDS," he wrote on Truth Social. "Republicans should stop using him as a reference point, his show is dead!"

In 2012, Donald made fun of Cher and called her "an average talent" who was "out of touch in reality" after the singer ripped Mitt Romney on X. She also branded Donald "pompous" and "mean-spirited" for his comments about Barack Obama's birth certificate.

"Cher is somewhat of a loser. She's lonely. She's unhappy. She's very miserable," Donald wrote on X, adding, "@cher should spend more time focusing on her family and dying career!"

Cher told The Guardian in 2023 that she would leave the country if Donald was re-elected.

Ever since Donald started his 2016 campaign, Chrissy Teigen consistently mocked the ex-president and called him out in her interviews.

She told USA Today in 2017, "I've been [trolling him] forever and I take pride in that. I can’t believe somebody could actually do this all day, every day, and still be president," she quipped at the time. "If I mysteriously go missing in the next four years, then that’s what happened."

In 2019, Donald called Chrissy "John Legend's filthy-mouthed wife." The model, on the other hand, responded by referring to him as "p---- a—b----."

Heidi Klum offered a savage response when the Republican presidential candidate told The New York Times she was "no longer a 10" in a 2017 interview.

The former Victoria's Secret Angel posted a 12-second video, showing herself wearing a white tee with the number 10 on it. A man with Donald's mask snatched the tag and revealed the new number, "9.99."

"#TrumpHasSpoken #sadly #9.99 #NoLongerA10 #IHadAGoodRun #donaldtrump #HeidiTrumpsTrump #BeautyIsInTheEyeOfTheBeheld," Heidi captioned the post.

Donald and Jimmy Kimmel have been exchanging tirades since the host started criticizing the ex-POTUS on Jimmy Kimmel Live! in 2016 amid the ex-president's campaign run.

One of their most recent exchanges occurred after Jimmy hosted the 2024 Oscars, where he made several jokes about Donald.

However, Donald shot back, calling him a horrible host.

"It was a CLASSIC CHOKE, one of the biggest ever in show business, and to top it off, he forgot to say the famous and mandatory line, ‘AND THE WINNER IS.’ Instead he stammered around as he opened the envelope," said the 45th U.S. president.

Jimmy did not let Donald have the last word as he asked the politician on his show, "Isn't it past your jail time?"

"I guess I shouldn’t be surprised," he told his show's viewers. "Donald Trump has said I’m not talented so many times Eric [Trump] is starting to get jealous. But what he doesn’t realize is that I love this. I love that this bothered him so much, I love that Fox picked a news guy nobody knows to interview him, and I especially love when he tries to spin the fact that everyone was laughing at him into a positive."

Madonna called out Donald while speaking at a Women's March in 2017 following his comments about women.

"Yes, I have thought an awful lot about blowing up the White House. But I know that this won't change anything," she told the crowd in Washington, D.C. The Queen of Pop, however, issued an apology after her statement sparked controversy.

On the other hand, Donald told Sean Hannity that Madonna's words were "disgusting" and that what she did "was disgraceful" to the U.S.

Once a Donald supporter, Mark Cuban formally announced he was a "#NeverTrump" and endorsed Hillary for president in July 2016.

"I don't hate the guy. Just don't want him to be president," he said of Donald.

Donald and Megyn Kelly's feud broke out in 2015 when the journalist asked him about his treatment of women and how he called them "fat pigs, dogs, slobs and disgusting animals."

After the interview, the 78-year-old media personality started targeting her in his social media posts. Months later, she told Charlie Rose she never wanted to fight with him in the first place.

"He was obviously upset. That's fine. He's running for president, it's not a fun business, there's going to be ups and downs, and I know he considered that a down," said Megyn. "So we just wanted to forge forward and try to put it behind us, not pour any more fuel on that fire."

Despite sharing the comment, Donald continuously attacked Megyn and reportedly brought up the debate question "a lot."

After Donald mocked a disabled reporter, Meryl Streep took her chance to criticize the politician in her Cecil B. DeMille Award acceptance speech at the 2017 Golden Globes.

"And this instinct to humiliate, when it's modeled by someone in the public platform, by someone powerful, it filters down into everybody's life because it kind of gives permission for other people to do the same thing. Disrespect invites disrespect. Violence incites violence," she stated.

In April 2011, Robert De Niro and Donald exchanged scathing statements after the former Trumped! host questioned Barack Obama's citizenship status.

"A lot of these guys, their intentions are not even good. They're just playing the game. And they're playing with people's lives," Robert told NBC News' Brian Williams, confirming Donald was among the people he was talking about. "It's crazy. They're making statements about people that they don't even back up. Go get the facts before you start saying things about people."

Meanwhile, Donald responded a few days later during his appearance on Fox & Friends, saying Robert was "not the brightest bulb on the planet."

In 2016, the Killers of the Flower Moon actor showered Donald with insults, saying he wanted to punch him before calling him a "pig," "con" and "b------- artist."

Over a decade later, Robert joined the celebrities who supported Donald's conviction in May when a Manhattan Criminal Courthouse jury found him guilty of 34 counts of crimes in the hush money trial.

Long before Donald became the president, Rosie O'Donnell already clashed with him after he allowed Tara Conner to retain her title in 2006 despite drug use and underage drinking allegations. She also targeted Donald's personal life and mocked his past marriages.

"[He] left the first wife — had an affair," Rosie said. "[He] had kids both times, but he's the moral compass for 20-year-olds in America. Donald, sit and spin, my friend."