Today, Kaitlin Olson has an incredibly high profile as the star of two of the biggest shows on television — It’s Always Sunny in Philadelphia, which just wrapped its seventeenth season, and crime drama High Potential, which kicks off its second season on September 16, 2025, at 10 pm EST. But over 20 years ago, long before she was a household name, Drew Carey knew that Olson was headed for stardom — and “felt lucky” to cast her in her first breakthrough role on his show.

Olson played Traylor, one of Drew’s coworkers at NeverEndingStore.com, on The Drew Carey Show from 2002 to 2004. But as Carey told ReMind earlier this year, even in those days, he knew that she was headed for stardom.

Shortly after she joined the show, Carey recalled that he and Drew Carey Show writer Clay Graham told Olson “‘you should have your own show. You’re so good. You should have your own show someday.’ And she was like, ‘oh, shucks, thanks.’ We’re like, ‘no, no, seriously, you’re really good. You should really have your own show,’ and look at her.”

Olson on ‘The Drew Carey Show.’ Courtesy Mohawk Productions/ Warner Bros. Television

Though at the time a few episodes of Curb Your Enthusiasm were Olson’s only real credits, Carey “thought, honestly, we felt lucky to get her on the show and cast her.” Olson already had an established comedy record as a member of Los Angeles’ legendary Groundlings (a group where stars from Kristen Wiig to Paul Reubens also cut their comedic teeth); but even with that, casting, Carey said, is an unpredictable process — there’s no guarantee they’ll actually work out. “And then when you pick somebody, you’re like, ‘I think they’re going to work out.’ And then when you see the first episode they’re on the show, you’re like, ‘Ooh, I knew it was going to be like this. I knew it was going to be this good.'”

A year after her Drew Carey role wrapped, Olson made her debut as Sweet Dee Reynolds on It’s Always Sunny in Philadelphia in August 2005.

In addition to Always Sunny and High Potential, Olson has a recurring role on Hacks as DJ, Deborah (Jean Smart)’s daughter, a role which nabbed her two Emmy nominations.

The Drew Carey Show celebrated the 30th anniversary of its premiere this month; you can catch the entire series streaming on Pluto TV. Hacks is available on HBO Max, and both Always Sunny and High Potential can be streamed on Hulu.