Born in Portland, Oregon, Kaitlin cultivated her passion for acting at the University of Oregon, where she got her Bachelor's degree in Theatre Arts. After her stint on stage, she moved to Los Angeles to pursue acting professionally. She began at The Groundlings Theatre in Hollywood, training ground to comic greats such as
Will Ferrell and
Phil Hartman. Kaitlin secured a coveted spot in The Groundlings Sunday Company, which proved to be an amazing showcase, leading to recurring roles on both
Curb Your Enthusiasm (2000), where Kaitlin plays "Becky", Larry's sister-in-law, and
The Drew Carey Show (1995), where she played "Traylor", Mimi's nemesis, for two seasons.
Olson also had the honor of joining
Drew Carey and several cast members of
Whose Line Is It Anyway? (1998) on a USO tour, performing improv shows for US troops in Bosnia, Kosovo, and Norway.
Soon after
The Drew Carey Show (1995) ended, Olson was cast as a series regular on the Fox series
Kelsey Grammer Presents: The Sketch Show (2005).
Previously, Olson has been a series regular on the Fox improv/hidden camera series
Meet the Marks (2002) and recurred on
Punk'd (2003) and
The Jamie Kennedy Experiment (2002). She has also had notable guest starring roles on
Out of Practice (2005) and
Miss Match (2003), opposite
Alicia Silverstone.
Olson starred as "Sweet Dee" on the FX breakout sitcom,
It's Always Sunny in Philadelphia (2005).