Inside Olivia Wilde and Jason Sudeikis’ Messy Break Up

Olivia Wilde was giving a presentation on stage in April when she was handed a tell-tale envelope by a mysterious attendee; she’d been served. Her custody battle with ex Jason Sudeikis was officially on.

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Once upon a time, Sudeikis and Wilde were a true Hollywood It couple. Wilde, the beautiful actress and Sudeikis, the charming comedian. A breakout star on Saturday Night Live, Sudeikis was already familiar face when he began dating Wilde in 2011. Since then, both their stars have risen.

Wilde is now an acclaimed director — and the girlfriend of pop sensation Harry Styles. And as that unlikely pairing makes for juicy tabloid fodder, her highly public breakup with Sudeikis has gotten increasingly messy.

Married Life

Olivia Wilde married her first husband Italian filmmaker and aristocrat Tao Ruspoli in 2003. It was when she was just 19 years old. They divorced in 2011… right around the time she met met Jason Sudeikis at an SNL wrap party in 2011.

At that point, Sudeikis had been on the show for six years and was already major TV star. Wilde was just beginning to break through. After finding fame on House, she starred in five major films during 2011.

Two years later, the celebrity couple got engaged. And though they never tied the knot officially, they soon had two children together: a son, Otis, and a daughter, Daisy. The pair was born in 2014 and 2016, respectively. Since then, Sudeikis and Wilde have maintained a seemingly happy public presence; so it came as a shock to fans when they announced their split in 2020.

The timing was also particularly striking, as both actors were enjoying a sudden career upswing.

Recent Success

Recently, both Olivia Wilde and Jason Sudeikis branched out from their usual performance fare — to massive success. A shade more serious than his standard comedy, Sudeikis now stars on Ted Lasso, the smash-hit, feel-good Apple TV+ show. Playing the titular soccer coach, Sudeikis won an Emmy for the role in 2021 and was nominated again in 2022.

Wilde, too, was making waves a first-time director. Booksmart, her directorial debut, premiered in 2019 and was hailed by critics who said it signaled a new era for female-driven, coming-of-age stories. After Booksmart, Wilde was chosen to direct the highly anticipated Don’t Worry Darling: a high-budget, star-studded thriller.

And that’s where the trouble really began.

A Public Serving

Along with basically the rest of the world, Olivia Wilde fell for Harry Styles last year. He stars as the male lead in Don’t Worry Darling, opposite Florence Pugh, a role that signifies his maturing image. Ten years Wilde’s junior, Styles first burst into the public eye as part of the boy band One Direction. Though he’s always churned out dependable pop hits, Styles is now heralded as a bona fide king of genre — as well as a style icon and, maybe, just maybe, a movie star.

That all depends on Don’t Worry Darling.

A peak era for both Styles and Wilde, their romance — and the upcoming film — is fascinating to a broad crossover of followers. So when Wilde was served custody papers while promoting the movie, the world took notice.

At a CinemaCon presentation in April, Olivia Wilde was delivering a presentation about Don’t Worry Darling when an audience member approached the stage, handing her a confidential envelope. Though Wilde seemed to maintain her composure and finish the talk, the reality was undeniable: she’d been served, by Jason Sudeikis, regarding the custody of her two children.

Since the ‘serving’ …

Since then, Wilde has been increasingly vocal about the event, condemning the tactics of Jason Sudeikis’ legal team. Back in April, an official statement from the Sudeikis camp stated that he personally had “no prior knowledge” of the plans to serve Wilde so publicly. But that hasn’t stopped Wilde from pushing her side of the story. After all, it was a polarizing move.

“He could have served me discreetly, but instead he chose to serve me in the most aggressive manner possible,” Wilde said in early August, according to the Daily Mail. “The fact that Jason would embarrass me professionally and put our personal conflict on public display in this manner is extremely contrary to our children’s best interests.”

In a new Variety profile, Wilde goes further to characterize her ex, apparently doubting whether he was truly ignorant about the CinemaCon ambush. “The hurdles that you had to jump through to get into that room with several badges, plus special COVID tests that had to be taken days in advance, which gave you wristbands that were necessary to gain access to the event — this was something that required forethought,” Wilde said.

Wilde also added that her kids were the real victims. “The victims were an 8- and 5-year-old, and that’s really sad. I chose to become an actress; I willingly walked into the spotlight. But it’s not something my children have asked for,” she said. “And when my kids are dragged into it, it’s deeply painful.”

Her statements have brought further attention on the whole incident… just as Don’t Worry Darling is about to hit theaters. But there’s even more controversy behind-the-scenes.

On-Set Drama

In the same Variety profile, Olivia Wilde uses her position to slam actor Shia LaBeouf. The actor was first slated to star in Don’t Worry Darling. “He has a process that, in some ways, seems to require a combative energy,” Wilde said, going on to say that, “With a movie like this, I knew that I was going to be asking Florence [Pugh] to be in very vulnerable situations, and my priority was making her feel safe and making her feel supported.”

Shia LeBeouf Situation

Around the time that filming was taking place, LaBeouf was sued by his ex FKA Twigs over claims of domestic abuse. Presumably, this is what Wilde is referring to when, in Variety, she says: “A lot came to light after this happened that really troubled me, in terms of [LaBeouf’s] behavior.”

And that’s a nice sentiment… if it were true. LeBouf insists that he was not fired from Don’t Worry Darling; he quit. And he has some pretty damning evidence to prove it.

The (admittedly volatile) actor shared videos online which show Wilde begging for him to return to the production. In the selfie recording, she even seems to throw Pugh under the bus in favor of retaining LeBeouf. Saying, “You know, I think this might be a bit of a wake-up call for Miss Flo… If she really commits, if she really puts her mind and heart into it at this point and if you guys can make peace… Is there hope?”

The desperate bid read as two-faced to most viewers, especially as Wilde continues on her outspoken press tour. The language, particularly “Miss Flo,” also alludes to some bad blood between Wilde and Pugh. Though Wilde has lauded Pugh’s latest performance, the actress has notably refrained from publicizing the venture on her active social media channels.

Don’t Worry Darling premieres officially on September 23… and is already earning lukewarm reviews. But even if the movie bombs, it’s worth its weight in pop culture sh*t-show spectacle.

What do you think?

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