A star is scorned: Trump’s 20-year feud with Hollywood

2 weeks ago 13

As America’s political establishment draws its battle lines with enemies in Hollywood, real and imagined, the lingering unasked question – just how quickly can sidelined talk show host Jimmy Kimmel return to TV screens? – is a tough one to answer.

When these scandals erupt, the key players tend to play a waiting game. Eventually the opinion-fuelled American news cycle will be hungry for fresher stories. And the political establishment, who need fresh meat to feed the voter rage machine, will move on to search for more viable targets.

Happier times … Donald Trump, then a presidential candidate, on Jimmy Kimmel’s late-night show in 2016.

But this scandal, portrayed largely as a simmering conflict between the political establishment in the White House and the talk-show-powered Hollywood satire machine, has cut America’s political divide deeply.

It is true that this is about opposing ideas of politics and propriety, and a fairly bendy interpretation of America’s free-speech guarantee – the much-discussed, much-misunderstood First Amendment. But it is also a story about big dollars and government red tape.

At one level, the key players are: Nexstar, the TV-station owning company whose threat to pull Kimmel started the brawl; Sinclair, another conservative TV-station owning group, which followed suit; and Tegna, the TV-station owning company that Nexstar wants to merge with.

Last week Nexstar announced a $US6.2 billion ($9.4 billion) acquisition of Tegna, a deal that would give the merged entity ownership of about 80 per cent of US local TV station markets, well above the Federal Communications Commission-stipulated cap of 39 per cent. The FCC, headed by a Trump appointee, has to approve (or reject) that proposed merger.

US President Donald Trump said Jimmy Kimmel was ‘fired’ for bad ratings and because he had ‘no talent’.

But at another level there is a wider and more personal historical mosaic around Trump’s relationship with Hollywood, a now-boiling pot for which the match was lit 21 years ago, on September 19, 2004, at the Shrine Auditorium in Los Angeles. (Happy anniversary?)

The Apprentice, the reality competition program that helped reshaped Donald Trump’s public persona and gave him the catchphrase “You’re fired!” was nominated for an Emmy, but The Amazing Race won.

“I got screwed out of an Emmy,” he said on The Celebrity Apprentice a decade later, reflecting on the loss. “Everybody thought I was gonna win it. When they announced the winner, I stood up before the winner was announced and I started walking for the Emmy. And then they announced the most boring show on television, The Amazing Race.”

The Apprentice was nominated a second time in 2005 and did not win. Trump himself was nominated in 2006 and did not win. And to add insult to apparent injury, The Celebrity Apprentice was never even nominated. To put those non-numbers in context, Arnold Schwarzenegger, Barack Obama and Al Gore have two Emmys each.

Trump firing a contestant in a season of The Apprentice.

Hillary Clinton, mercifully, has no Emmys, but she does have a Grammy. Which, to the casual political ear, sounds enough like an Emmy to create problems. And Obama, on top of his two Emmys, has a Nobel Peace Prize, which is of course a whole other problem and a discussion for another day.

That disaffection has laid the groundwork for a slowly disintegrating relationship between the famous billionaire and president-in-waiting and the Hollywood fame machine.

From 2016 Trump took aim at Saturday Night Live, which was featuring Alec Baldwin in sketches about him. In 2018 he fired a missive at “the unfunny lamestream media” and singled out talk show hosts Stephen Colbert and Jimmy Fallon. At a rally in 2020 he referred to “the deep state, the radical left, the Hollywood crazies”. And at a campaign rally in 2024 he referred to “the Hollywood crazies, the liberal elites who lecture you about values while they poison our country”.

All of that is difficult to juxtapose with the fact that Trump played himself in Home Alone 2: Lost in New York, episodes of The Fresh Prince of Bel-Air (with then-wife Marla Maples), The Nanny (with now-arch-nemesis Rosie O’Donnell) and Sex and the City, the film Zoolander (with current wife Melania) and a handful of other films and TV shows.

Whatever Trump is, he’s not uncomfortable in front of the TV or film camera. He even featured in a sketch on stage at the Emmys, playing the husband in a performance of the theme from Green Acres with Will & Grace’s Megan Mullally. The same Emmys he still periodically rails against.

Back in 2002 Bill Maher’s show Politically Incorrect was axed by ABC, the same network that has iced Kimmel, due to a controversial remark. Maher was off-air for eight months before Real Time with Bill Maher launched on HBO. And in 2007 broadcaster Don Imus was fired by CBS Radio and MSNBC for offensive remarks and also spent eight months in broadcast purgatory.

Jon Stewart hosts the Trumped-up edition of the Daily Show.

In 2013 Alec Baldwin’s MSNBC series Up Late was axed after he used an anti-gay slur in a confrontation with a photographer. It never returned. In 2018 Megyn Kelly questioned whether “blackface” was racist and lost her NBC show. (She later apologised.) And in 2021 the CBS show The Talk was put on hiatus after co-host Sharon Osbourne defended British TV host Piers Morgan. The show returned but Osbourne did not.

The list of people whose off-the-cuff or calculated offences have led to them being sidelined is long: Morgan, Roseanne Barr, Jeremy Clarkson and, in Australia, Sam Newman and Ron Casey. So where does that leave Jimmy Kimmel? His remarks don’t match some of those low benchmarks for offence, but they still provoked substantial anger.

As Hollywood grapples with the answer to that question, the country’s satirist-in-chief Jon Stewart opened The Daily Show with an anxious editorial in front of a Trump Oval Office-style, gilt-edged do-over of his set.

“Some naysayers may argue that this administration’s speech concerns are merely a cynical ploy, a thin gruel of a ruse, a smoke screen to obscure an unprecedented consolidation of power and unitary intimidation, principleless and coldly antithetical to any experiment in a constitutional republic governance,” Stewart said. “Some people would say that. Not me, though. I think it’s great!”

Find out the next TV, streaming series and movies to add to your must-sees. Get The Watchlist delivered every Thursday.