“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.Credit: Screenshot
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 Livewhich 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 Yorkepisodes 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 Citythe 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.Credit:
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.
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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!”
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