Why Jamie From The Progressive Commercials Looks So Familiar

Playing Jamie from Progressive has made comedian Jim Cashman one of the actors who made a ton of money through commercials. Cashman has a net worth of around $3 million and pulls in approximately $500,000 a year playing Flo from Progressive's sidekick. Besides his commercial work, Cashman has an accomplished resume which includes television credits dating back to 1999. His TV work includes appearances in massive shows, such as popping up in two episodes of "Just Shoot Me," and later in "Grey's Anatomy," and "It's Always Sunny in Philadelphia." In 2018, Cashman tweeted about appearing in Season 13 of "Always Sunny," taking to X, formerly Twitter, to share: "Very excited to take a trip to Philly tonight! Thanks @RMcElhenney @GlennHowerton @KaitlinOlson & Charlie!"

Fans may recognize Jamie from Progressive for his TV work, but he also appeared in the 2016 film "The Boss," which starred Melissa McCarthy and was written and directed by her and her husband, Ben Falcone. After working on that film together, McCarthy re-teamed with Cashman the following year for the TV movie "Amy's Brother." McCarthy and Falcone were executive producers, and they tapped Cashman and his writing partner, Mitch Silpa, to write and produce the project.

McCarthy's "The Boss" character was created when she was part of the comedy troupe The Groundlings, where she met Cashman. Fans may not know that Cashman and Flo from Progressive were also connected through that comedy school.

Jamie and Flo from Progressive go way back

Similar to Jim Cashman, fans may have seen Flo from Progressive — actor Stephanie Courtney — in her extensive television work. Before breaking through on TV, both actors cut their teeth at The Groundlings, where they honed their improv skills. "You meet a bunch of people that don't just become your friends but your comedic colleagues," Cashman told the Los Angeles Times in May 2014, when he was still a member of the comedy troupe. "It's who you turn to creatively," he added.

Well before she became known for her Flo character, Courtney struggled to make a living while trying to break through in TV and commercial work. "And then once I was in the Groundlings and I became a company member, we would teach. Before that, I delivered the Zone Diet," she told Backstage in May 2020 when discussing her early days as an actor.

Thanks in part to the connection Progressive's two stars, Flo and Jamie, had to the comedy program, the insurance company made a sizeable donation to The Groundlings in February 2021. The donation was made to the Groundlings Diversity Scholarship which would help some 300 students participate in classes and receive private teaching at the impro school. "So many good things in my life can be traced right back to this theater," Courtney said in a statement at the time, per Broadway World. Not only did Cashman have a connection to Flo from The Groundlings, but his wife was also a member.

Jim Cashman was on a popular sitcom with his wife

Jim Cashman is married to fellow actor and comedian Michelle Noh. The couple tied the knot years before he landed the gig as Jamie in the Progressive commercials, as they celebrated their 20th wedding anniversary in November 2023. Cashman has been a vocal supporter of his wife's projects, such as her work on the "Interstate" musical. "Beyond proud of this woman," he wrote on X in March 2018, while retweeting Noh.

The couple has also worked together, as they appeared on the "Airplane!" episode of "The Goldbergs" in 2020. That episode was a riff on the '70s comedy classic of the same name. Not only was it a chance for the real-life couple to perform together, but it was a mini-reunion for Jamie and Flo from Progressive, as Stephanie Courtney played Essie Karp on 31 episodes of the popular ABC sitcom. Cashman and Noh also got together with Courtney a slew of celebrities, for a fundraising performance at The Groundlings theater in October 2023, to raise money for below-the-line workers during the writers and actors strikes.

Cashman has kept a low profile on social media since 2021, but Noh has delivered plenty of updates on the couple as she routinely posts snaps of the pair and their children on her Instagram page.