Highlights

• Sarah Silverman's Emmy-winning "I'm f--ing Matt Damon" video gave Jimmy Kimmel's show a big breakthrough after five years.
• Jimmy Kimmel and Sarah Silverman started dating in 2002 and had a tumultuous seven-year relationship before finally breaking up for good in 2009.
• Despite their split, Kimmel and Silverman eventually became close friends and consider each other like brothers, supporting each other's careers.

Jimmy Kimmel is the ninth richest late-night talk show host in the world. He's amassed a net worth of $50 million since he started hosting Jimmy Kimmel Live! in 2003. But it wasn't easy getting there. It took him five years to get a decent viewership. In 2022, Kimmel told Andy Cohen that his ex, "cringe" comedian Sarah Silverman, was the one who gave his show its big break.

The two started dating in 2002 after the forgotten Seinfeld alum said his future boyfriend was "fat" and had "no charisma." Then, after their 2009 split, it took a while for them to be "like brothers." Here's how they've supported each other's careers throughout the years.

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When Cohen asked Kimmel how long it took for his show "to get to a place where... it was getting the ratings and attention that were big and in a great place," the latter said it took five years. He said it was Silverman's Emmy-winning "I'm f--ing Matt Damon" video that helped him get there.

"That's when people really woke up to the show and noticed what we're doing," Kimmel said of Silverman's hit appearance on his show. "There were occasional moments along the way before that, but that's where it really kicked in."

He went on to share that the viral video was made for him on his 40th birthday. "We happened to be on writer's strike at that time," Kimmel recalled. "So it was a good five years in before [that breakout moment]." However, ABC's former CEO and current Disney boss, Bob Iger said it took Kimmel "10 years to get good at it." The host thought Iger was "right" about it, though.

In January 2023, on Jimmy Kimmel Live!'s 20th anniversary, the funnyman thanked the "many great people" behind the show, saying "very few people expected us to make it this far." After a few jokes like selling his soul to the devil for fame, he got emotional, saying: "It takes a lot of people to make something this dumb, and we've covered a lot of dumb stuff over the past 20 years."

Jimmy Kimmel "was very intent on retiring" during the 2023 SAG-AFTRA strike but changed his mind because it's "nice to work."

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Sarah Silverman Said "Fat" Jimmy Kimmel Had "No Charisma" When They First Met

In 2001, amid Kimmel's divorce from Gina Maddy, he met Silverman for the first time at the New York Friars Club Roast of Hugh Hefner. There, the latter roasted her future beau, saying he was "fat" with "no charisma." Soon, they "started hanging out and watching movies together" until "one night we were watching Broadway Danny Rose. Jimmy went in for the first kiss," Silverman recounted.

"Both of us — we were probably nose to nose for what seemed like forty minutes before either of us had the guts to just go ahead and kiss," she said of their first kiss. "But once we did, we started making out like crazy. It had been festering for a very long time."

They started dating in 2002 when Kimmel's divorce was finalized. A year into the relationship, Silverman said she couldn't believe he called her boyfriend "fat" on their first meeting. "It's weird looking back at that. I didn't know him at all back then," the actress told Entertainment Weekly in 2003. "I can't believe I called him fat. Knowing him now, it's funny because he has such a thin personality."

Here's a brief timeline of their seven-year relationship:

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How Jimmy Kimmel And Sarah Silverman Became "Like Brothers" After Their Split

In 2017, Kimmel told GQ that he and Silverman were "like brothers." He said "it doesn't make sense to me that people would erase a big part of their lives. It's not like we didn't spend every day together for many years. We did, and we have a lot of things in common and mutual friends. I'll see something in the news and think, Oh, my God. I have to tell Sarah about this."

But speaking to Cohen in 2019, Kimmel admitted that "it definitely took some time to be comfortable enough to be friends again," In 2010, Silverman told Playboy that they "had every intention of spending the rest of our lives with each other." The late-night host eventually married screenwriter, Molly McNearney in 2013. A year later, Silverman tweeted that she'd never get married.

"I just don't understand the instinct to want to join a club that is elitist," Silverman said of marriages. "I mean it's like joining a country club that doesn't allow Jews or black people. What's the difference?"

In 2020, the Maestro star started dating The Daily Show's former showrunner, Rory Albanese. When Howard Stern asked if Silverman could see herself marrying Albanese, she said: "We'd like to just be together all the time forever. If Rory was someone who was like, 'I need to be married,' then yeah, I'd think about it, I guess." The two are still happily dating. In 2022, Silverman said she "[shares] a toothbrush with [her] boyfriend."

Sarah Silverman started dating her boyfriend Rory Albanese in late 2020 after remotely playing video games together during the COVID-19 pandemic.

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