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For a time, Jason Sudeikis’ messy split with Olivia Wilde was the talk of the town, with every detail of their fractured relationship dissected by the media. However, the drama in his personal life didn’t stop there. Turns out the pressures of his skyrocketing career when he was just starting out, particularly his high-profile job onSNL, also took out his first marriage.

As Jason Sudeikis’s star power grew, so did the strain on his marriage to Kay Cannon, a talented screenwriter and producer. With his rising fame and nonstop workload, the relationship faced mounting stress, eventually leading to its breakup.
HowSNLBecame the Third Wheel in Jason Sudeikis and Kay Cannon’s Relationship
WhenJason Sudeikislanded his first big break withSNL, he was navigating a tough period in his life. At the time, the actor people now adore was living in Los Angeles with his girlfriend, Kay Cannon, juggling sketch comedy gigs and performing eight shows a week. The opportunity to audition forSNLand secure a role as a writer was a dream come true for him.
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However, the excitement of this new chapter came with its own set of challenges, particularly when it came to his relationship with Kay Cannon. In an interview withGQ, he revealed,
It was like winning a gold medal in the thing you’ve never even trained for. You just happen to be good at the triple jump, and you really love the long jump.

Juggling his newSNLjob and a long-distance relationship was challenging for Sudeikis. Missing his wife and performing live, he approached Lorne Michaels, requesting a spot on the cast. To which he said,
He had the best line. I go, ‘I had to give up two things I love the most to take this writing job: performing and living with my wife.’ And on a dime, he just goes, ‘Well, if you had to choose one…’ ”

TheTed Lassoactor met Cannon, known for her work inPitch Perfect, in Chicago’s Second City improv scene in the early 2000s. They wed in 2004 after Sudeikis relocated to New York for the writing gig atSaturday Night Live.Despite their strong start, the pressures of a long-distance relationship took their toll, leading to their separation in 2008 and eventual divorce in February 2010.
TheTed LassoStar is on a Mission to Find His Perfect Match!
It’s well-known that life in the spotlight comes with its fair share of challenges, and managing a personal life often takes a hit. Jason Sudeikis is no exception to this rule. Despite navigating the ups and downs of his relationships, he didn’t let his heartbreak with Kay Cannon hold him back. Shortly after their split, he was briefly linked withMad Menactress January Jones, but their romance fizzled out after just a few months.
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In 2011, Sudeikis began a relationship with Olivia Wilde, and the couple, who share two children, seemed to be going strong. Although they got engaged in 2012, they never married. Trouble began to brew in their paradise around 2020, and their relationship ultimately ended soon after. The split was messy, butthe dramathat followed was even messier, alas that’s a story for another time.
Since then, the actor has been seen with Keeley Hazell and most recently he was seen enjoying a night out in West Hollywood, California, with Elsie Hewitt in January as perPage Six.

By the looks of it, he’s not letting these minor setbacks derail him. He’s focused on keeping his thriving professional career on its impressive trajectory while also ensuring that his success in the spotlight doesn’t overshadow his pursuit of happiness off-screen.
Ted Lasso is streaming on Apple TV.
Sampurna Banerjee
Articles Published :1803
Sampurna Banerjee is an Entertainment Writer at FandomWire, and she’s written over 1,700 articles! She covers everything from celebrity news to the latest superhero buzz, streaming shows, and fan theories. If it’s trending in pop culture, Sampurna’s probably already on it.When she’s not working, you’ll probably find her rewatching The Office (again), getting into debates about Marvel’s timeline, or diving deep into Christopher Nolan movies for the hundredth time. She’s not just writing about entertainment, she’s living it.
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Jason SudeikisOlivia WildeSNLTed Lasso
