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.