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The good, the bad, and the ‘unusually attractive’: Donald Trump’s celebrity obsessions

The good, the bad, and the ‘unusually attractive’: Donald Trump’s celebrity obsessions

Celebrities hanging around with US presidents is not a new phenomenon — but when it comes to hating on fellow celebrities no one does it quite like former president Donald Trump.

Other presidents simply befriended celebs — Bill Clinton famously played his saxophone for Arsenio Hall and has been photographed with numerous A-listers, including Brad Pitt, Tom Cruise, and Charlize Theron, among others, both during and after his presidency.

Barack Obama’s inauguration was attended by Jay Z, Sean ‘Diddy’ Combs, and Magic Johnson, and former First Lady Michelle Obama’s 50th birthday party was held on Oprah Winfrey’s estate.

But Trump has been starting fights and insulting other famous people for years — here’s some who’ve caught his attention and wrath.

Alec Baldwin

Trump has long despised Alec Baldwin, likely because Baldwin is well known for lampooning the former president by portraying him on Saturday Night Live. He even won an Emmy for his skewering performance.

Alec Baldwin’s Saturday Night Live impersonations of Trump won him an Emmy – but also the hatred of his target
Alec Baldwin’s Saturday Night Live impersonations of Trump won him an Emmy – but also the hatred of his target (NBC)

In 2018, Trump roasted Baldwin when he suggested his career was “dying” and complained that his impersonation was “agony.”

“Alec Baldwin, whose dying mediocre career was saved by his terrible impersonation of me on SNL, now says playing me was agony,” Trump wrote on Twitter. “Alec, it was agony for those who were forced to watch. Bring back Darrell Hammond, funnier and a far greater talent!”

He also weighed in on Baldwin’s legal troubles following the fatal shooting of Halyna Hutchins on the set of the Baldwin-produced western, Rust in 2021.

“He’s a troubled guy,” Trump said of Baldwin during an interview on conservative radio host Chris Stigall’s podcast in 2021. “There’s something wrong with him. I’ve watched him for years. He gets into fistfights with reporters … He’s a cuckoo-bird. He’s a nutjob. And usually, when there’s somebody like that, you know, in my opinion, he had something to do with it.”

Robert De Niro

The Goodfellas and Casino star has criticized Trump for years, a fact which has not been lost on the former president.

Fellow New Yorker Robert De Niro has become one of Trump’s most outspoken critics
Fellow New Yorker Robert De Niro has become one of Trump’s most outspoken critics (AFP via Getty Images)

“Lying has become just another tool in the charlatan’s arsenal,” De Niro said during the Gotham Awards ceremony in December. “The former president lied to us more than 30,000 times during his four years in office, and he’s keeping up the pace in his current campaign of retribution. But with all his lies, he can’t hide his soul.”

Trump was not pleased.

“De Niro should focus on his life, which is a mess, rather than the lives of others. He has become a total loser, as the World watches, waits, and laughs!” Trump wrote in a Truth Social post after the speech. “He has become unwatchable both in movies, and with the FOOLS that destroyed the Academy Awards, bringing them from one of the top shows in the Country to a Low Rated afterthought.”

Earlier this year, De Niro held a protest outside the courthouse where Trump’s New York hush money trial was taking place and called the former president a “monster.”

Trump shot back, calling De Niro “small” and a “wacko.”

“Robert, whose movies, artistry, and brand have gone WAY DOWN IN VALUE since he entered the political arena at the request of Crooked Joe Biden, looked so pathetic and sad out there. Where have you gone Joe DiMaggio!!!” the former president wrote on Truth Social.

Taylor Swift

Trump’s relationship with the Eras tour megastar is not nearly as contentious as his relationship with De Niro and Baldwin.

Taylor Swift told Trump that Americans would ‘vote you out in November’ ahead of the 2020 election
Taylor Swift told Trump that Americans would ‘vote you out in November’ ahead of the 2020 election (AFP via Getty Images)

Swift has expressed generally progressive political views, saying in interviews that she is pro-choice and is against any kind of gender or sexual orientation discrimination. In a 2019 interview with The Guardian, she shared her thoughts on Trump’s presidency, calling it an “autocracy.”

Following Trump’s “when the looting starts the shooting starts” comments after the murder of George Floyd, Swift laid into the former president, telling him on X that “we will vote you out in November.”

“After stoking the fires of white supremacy and racism your entire presidency, you have the nerve to feign moral superiority before threatening violence? ‘When the looting starts the shooting starts’??? We will vote you out in November. @realdonaldtrump,” she wrote.

Two years later, Trump commented on Swift, but mostly on how hot he thinks she is.

“I think she’s beautiful – very beautiful! I find her very beautiful. I think she’s liberal. She probably doesn’t like Trump. I hear she’s very talented,” Trump reportedly said, according to Ramin Setoodeh’s new book, Apprentice in Wonderland. “I think she’s very beautiful, actually – unusually beautiful!”

He also seemed genuinely surprised that Swift was a “liberal.”

“She is liberal, or is that just an act?” he asked Setoodeh in 2023. “She’s legitimately liberal? It’s not an act? It surprises me that a country star can be successful being liberal.”

Kristen Stewart and Robert Pattinson

Four years before Donald Trump became president, he spent an unusual amount of time on Twitter giving his perspective on the high-profile celebrity breakup of Twilight co-stars Robert Pattinson and Kristen Stewart.

Kristen Stewart and Robert Pattinson in ‘Twilight'. Trump encouraged Pattinson not to ‘take back’ Stewart in 2012 after she cheated on him
Kristen Stewart and Robert Pattinson in ‘Twilight’. Trump encouraged Pattinson not to ‘take back’ Stewart in 2012 after she cheated on him (Netflix/Summit Entertainment)

“Robert Pattinson should not take back Kristen Stewart,” Trump wrote at the time. “[Stewart] cheated on him like a dog and will do it again — just watch. He can do much better!”

At the time, Stewart had cheated on Pattinson with director Rupert Sanders, who helmed Snow White and the Huntsman, which featured the actress.

“Lots of response to my Pattinson/Kristen Stewart reunion. She will cheat again–100 certain–am I ever wrong?,” Trump wrote. “So many tweets & stories on Stewart/Pattinson Look, it doesn’t matter– the relationship will never be the same. It is permanently broken.”

He insisted at the time that “everyone knows I am right” that Pattinson should dump Stewart, and that “in a couple of years [Pattinson] will thank me.”

Trump even offered Pattinson an invite to that year’s Miss Universe contest, and later praised his look at a Twilight series premier.

“Robert Pattinson is putting on a good face for the release of Twilight. He took my advice on Kristen Stewart…I hope!” Trump wrote.

Kim and Khloe Kardashian

In 2016, just before the presidential election, the Huffington Post ran a story citing anonymous staffers on Trump’s Celebrity Apprentice who claimed that he had frequently disparaged contestant Khloe Kardashian on set.

Kim Kardashian, left, and Khloe Kardashian. Trump allegedly called Khloe a ‘fat piglet’ on the set of The Apprentice, and said he felt betrayed by Kim after she celebrated Joe Biden’s election victory in 2020
Kim Kardashian, left, and Khloe Kardashian. Trump allegedly called Khloe a ‘fat piglet’ on the set of The Apprentice, and said he felt betrayed by Kim after she celebrated Joe Biden’s election victory in 2020 (Getty Images)

He reportedly called her a “fat piglet” and complained that his production couldn’t get the “hot one,” referring to Kim Kardashian.

“What is this? We can’t even get the hot one?” he allegedly said. “Why did we get the ugly Kardashian?’”

Despite his alleged remarks about her sister, Kim Kardashian made inroads with Trump in 2018 concerning prison reform, and managed to pressure him to commute the sentence of Alice Johnson, a 63-year-old woman given life in prison without parole for a nonviolent drug offense.

Kim even praised some of Trump’s prison reforms during his 2020 presidential campaign. But he soured on the reality TV star after she celebrated Joe Biden’s victory over him in the 2020, according to Setoodeh.

“I was disappointed in Kim,” he reportedly told the author. “But with Kim, I did a lot of prison reform that she couldn’t get done with anyone else. Then, in order to be accepted by Hollywood, she didn’t endorse me.”

Trump then corrected himself and said that “someone” told him Kim did not endorse him.

Kanye West

There is arguably no celebrity that has brought more trouble to Trump than West, even though West was a supporter.

Kanye West and Trump after a meeting at Trump Tower in New York in 2016. Trump was thankful for West’s support until the rapper began voicing antisemitic views in 2022, leading to Trump calling him a ‘seriously troubled man’
Kanye West and Trump after a meeting at Trump Tower in New York in 2016. Trump was thankful for West’s support until the rapper began voicing antisemitic views in 2022, leading to Trump calling him a ‘seriously troubled man’ (AFP via Getty Images)

Trump told Extra host Mario Lopez in 2014 that he knew both West and Kim Kardashian “very well” and wished them well in their new marriage.

In 2020, after West announced he planned to run for president, Trump told Rolling Stone that the rapper had said “very nice things about me in the past…extremely positive things,” and that he hoped to run against him one day.

West made an unsuccesful attempt at running in 2020, failing to collect enough signatures to get on state ballots.

In 2016, West told a crowd in San Jose that if he had voted, he would have voted for Trump.

West praised Trump for much of his presidency, earning a tweet from the former president at one point saying “thank you Kanye, very cool!”

“Thank you to Kanye West and the fact that he is willing to tell the TRUTH,” Trump tweeted after Kanye praised him in a 2018 Jimmy Kimmel Live! episode. “One new and great FACT – African American unemployment is the lowest ever recorded in the history of our Country. So honored by this. Thank you Kanye for your support. It is making a big difference!”

In 2022, following his divorce from Kim Kardashian, West took a bizarre turn and began making openly anti-semitic remarks and spending time with right-wing provocateur Candace Owens and white supremacist podcaster Nick Fuentes.

As public approval turned hard against West, he still maintained his support for Trump, and attended a dinner with the former president with Fuentes in tow.

Trump was blasted in the press for dining with an outspoken white supremacist and Holocaust denier, forcing him to distance himself from the event, insisting at the time that he did not know who Fuentes was. He also was forced to finally denounce his biggest fan, West.

Trump claimed that he was simply trying to help West, who he called a “seriously troubled man,” and that the guests West brought — Fuentes, specifically — were not invited to the dinner.

A month later, West appeared on Alex Jones’ InfoWars show in a face-obscuring black mask and said he “liked” Adolf Hitler.




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