Celebrities Who Made The Most Money From Getting Fired

Being fired is a stressful event that nobody wants to think about, especially celebrities who get to suffer the indignity of losing their job in the public eye. But along with their high-profile gigs come some seriously high-end benefits, one of which is almost always some kind of clause ensuring a certain amount of their salary right up front. In the film industry, this is known as a "pay or play" deal, which basically means when a star signs onto a film they're going to get paid whether the film gets made or not. And yes, this can include if they get fired from the film as well. Elsewhere in the entertainment world this is just known as a "guarantee," and in certain cases, having this legal paycheck protection written into their contract has worked out quite handsomely for some. Here are the celebrities who made the most money getting fired.

​Roger Ailes

Roger Ailes is the former CEO of Fox News, and the man who is generally regarded to have been the architect of the entire Fox News business model for the past 20 years. On July 21, 2016, he was forced to resign in the wake of former Fox News anchor Gretchen Carlson's sexual harassment lawsuit that paved the way for a slew of similar accusations. Though Ailes denies every accusation against him, at the time of this writing, over 20 women have filed complaints and lawsuits against the former Fox head honcho. One of the more particularly disturbing complaints against Ailes is from a woman who claimed Ailes exposed himself to her in his office when she was only 16 years old, and proceeded to chase her around the room when she rebuffed his advances.

For his decidedly shameful exit, Ailes is said to have received $40 million in severance pay according to leaked documents obtained by The Drudge Report (via The Guardian.) He even got to pretend like he was gracefully bowing out in order to not distract from the vital mission of the company via a letter he wrote to Rupert Murdoch which, among a lengthy list of his boasted achievements, also said, "Having spent 20 years building this historic business, I will not allow my presence to become a distraction from the work that must be done every day to ensure that Fox News and Fox Business continue to lead our industry."

Curiously enough, in October of 2016, he reportedly purchased a luxurious oceanfront mansion in West Palm Beach, FL for $37 million, a price tag so close to his reported severance, there's almost no chance it's a coincidence.

Bill O'Reilly

Like his former boss, Roger Ailes, Bill O'Reilly left his long-held seat at Fox News amidst a wave of sexual harassment claims. While O'Reilly had survived a similar, albeit smaller storm before, when he quietly settled out of court with former producer, Andrea Mackris, over harassment allegations in 2004, this time was different.

After The New York Times exposed $13 million dollars in out of court settlements paid to four women, and arranged by both O'Reilly and Fox News over the past several years, the public pressure to oust the outspoken pundit became too great to ignore. In the middle of his impromptu "vacation," it was announced that O'Reilly would not be returning to the airwaves. In another echo of Ailes, O'Reilly was similarly afforded the courtesy of being able to claim the decision to end his show was a mutual one. "After a thorough and careful review of the allegations, the company and Bill O'Reilly have agreed that Bill O'Reilly will not be returning to the Fox News Channel," read the statement from parent company 21st Century Fox.

But again, like his former boss, O'Reilly coasted out of a giant scandal with a windfall check the most lottery players only dream of. According to NBC News, two sources confirmed that his severance check could be as high as $25 million dollars. But still, O'Reilly is disappointed. "It is tremendously disheartening that we part ways due to completely unfounded claims. But that is the unfortunate reality many of us in the public eye must live with today," he said in an additional statement.

Charlie Sheen

As part of Charlie Sheen's public meltdown, he waged war with his then-boss, showrunner and creator of Two and a Half Men, Chuck Lorre. The two beefed publicly, with Sheen doing repeated, increasingly insane media appearances, and Lorre surreptitiously writing "vanity cards" that flashed briefly after the show's end credits. Ultimately, Sheen was terminated by CBS in a scathing 11-page letter that stated their grounds for his removal were "a felony offense involving moral turpitude."

Sheen, who was famously earning $1.8 million per episode at the time, filed a wrongful termination suit against Lorre and CBS seeking $100 million dollars. They ended up settling out of court for a rumored $25 million.

A TV analyst for Horizon Media told Fox 411 that Sheen still stood to make upwards of $100 million based on the backend agreement he had, which secured him royalties from syndication fees as well as "DVD sales and Netflix rentals." That means that when it was all said and done, Charlie Sheen probably made $125 million dollars off of a show from which he was not only fired, but also told his boss live on the radio to "suck his butt." Take our advice: Do not try this at your job. It won't work out the same way for you.

Marlon Wayans

This one may seem hard to believe, but Marlon Wayans was actually cast as Robin in Tim Burton's 1992 sequel, Batman Returns. Of course, this was long before Scary Movie and the questionable White Chicks were around to prove what a disastrous idea that truly would have been, but nevertheless, it wasn't meant to be. In an interview with io9 (via MTV), Wayans said, "I was actually supposed to play Robin, in Batman Returns about 15 years ago. But there were too many characters. I was cast, I was paid and everything. I still get residual checks."

He never specified the amount he was paid, but we feel confident in saying that we can all agree whatever that amount is, it's way, way too much. Wayans even offered his own theory on why the role never fully materialized for him. Speaking about Robin's eventual debut in Batman Forever, Wayans said, "I get why they picked Chris O'Donnell, because it would be messed up to have Batman and you've got Robin, and his bulge is somewhat bigger than Batman's. Batman would have a serious problem with that." Still think we were too harsh with that slam on his residual checks? Didn't think so.

Hilary Duff

When you think of Lizzie McGuire, you also think of a gun-toting, bank-robbing wild child who dies in a blaze of glory and a hail of gunfire, right? Yeah not exactly, but regardless, Hilary Duff was cast in a remake of Bonnie & Clyde in the lead role of the Depression Era femme fatale. But alas, she'd never empty the barrel clip of a tommy gun into her former Disney image, because she was dropped from the flick supposedly due to her pregnancy.

Of course, the producers of the film denied this was the case, telling The Hollywood Reporter, "Due to our obligations with investors and international buyers, it is imperative that we stick to our current schedule." They claimed that Duff was unavailable for when they wanted to start production. But thanks to her pay-or-play deal, Duff received a $100,000 payout for doing absolutely nothing. Although to hear it from her, she wasn't exactly thrilled about it. "I don't wanna give them any more press than they've already gotten off me ... I think [my] baby is a little bit more exciting," she told TMZ when asked about the situation. Listen, we've met babies, and they're cool and everything, but a hundred grand for doing nothing is the very definition of something to get excited about.

Billy Bush

The Access Hollywood scandal involving Billy Bush sent him plummeting from stardom faster than a lead balloon. Bush had just signed a contract with Today to host the 9 o'clock hour of the popular morning broadcast when the audio tape of him snickering at Donald Trump's lurid "locker room talk" was leaked. According to CNN, his contract was worth around $3 million dollars per year for three years, and Bush was only a few months into it when he was let go.

Rumors immediately surfaced the he was getting a $9 or $10 million dollar payout, which his rep quickly disputed. "There is no $10M agreement and that amount has not been discussed," Bush's lawyer, Marshall Grossman said in a statement. "The negotiations are productive in moving the parties away from litigation to resolution. Obviously there is more to be done before all of the terms of an agreement are reached and documented," he continued.

Ultimately, the settlement figure was never released, but according to TMZ's "sources with direct knowledge of the negotiations," Bush was "happy" with the number.

Conan O'Brien

When Conan O'Brien took the reins of his dream job, hosting The Tonight Show, he never imagined it would only last six months. But after a rocky start in the ratings, and a disastrous lead-in from Jay Leno's failed primetime experiment, the network attempted to shift The Tonight Show back to 12:05 AM to make room again for Leno in his old 11:35 PM time slot. It was the last straw for O'Brien, who told 60 Minutes that he felt like the environment at the network started to feel "toxic," and that he wasn't even sure if they wanted him to say. Ultimately, O'Brien resigned, but he suspected that he was pushed out with a backdoor assist by Leno, who negotiated behind the scenes to resume his spot at the top of late night.

O'Brien walked with a $32 million dollar payout, and of course, went on to land a new gig a TBS. Though he initially struggled with how the whole thing went down, O'Brien came to terms with it, saying, "It's crucial to me that anyone seeing this take...they take anything away from this it's I'm fine. I'm doing great. I hope people still find me comedically absurd and ridiculous. And I don't regret anything. I do believe and this might be my Catholic upbringing or Irish magical thinking, but I think things happen for a reason. I really do." Just off the top of our heads, we can think of around thirty-two million reasons nothing about this situation was that bad at all.

Ann Curry

The optics of Ann Curry's tearful 2012 Today exit made it seem like she'd been caught embezzling millions and was about to be cuffed and thrown into the back of a patrol car. And yes, she was fired from Today after only one year in the anchor seat and with ratings tanking, but it's not like NBC cut her loose completely.

In reality, Curry continued to work for NBC News for three more years, racking up accolades and awards along the way despite her infrequent appearances. She was also given the title of NBC News national and international correspondent and anchor-at-large, which reportedly came along with a continuing salary of $12 million per year, according to Page Six. Not only that, but when Curry did finally leave NBC news for good in 2015 to create her own media startup — which was "backed by NBCUniversal," incidentally — she negotiated a deal allowing her to "produce content for NBC News and other platforms and networks." So, once again she left a job only to still get money from that job along with a presumably substantially reduced workload. That does not sound like something to cry about.