Kaitlin Olson's journey as an actress began in Portland, Oregon, where she nurtured her passion for acting at the University of Oregon, earning a Bachelor's degree in Theatre Arts. Following her time on stage, she relocated to Los Angeles to pursue a professional acting career.
Her path led her to The Groundlings Theatre in Hollywood, a renowned institution that has spawned comedic greats such as Will Ferrell and Phil Hartman. Olson's talent and dedication earned her a coveted spot in The Groundlings Sunday Company, which served as an impressive showcase, ultimately leading to recurring roles on both Curb Your Enthusiasm and The Drew Carey Show.
In addition to her television work, Olson had the privilege of joining Drew Carey and other Whose Line Is It Anyway? cast members on a USO tour, performing improv shows for US troops stationed in Bosnia, Kosovo, and Norway.
After The Drew Carey Show concluded, Olson landed a series regular role on the Fox series Kelsey Grammer Presents: The Sketch Show. Prior to this, she had been a series regular on the Fox improv/hidden camera series Meet the Marks and had recurring roles on Punk'd and The Jamie Kennedy Experiment. Her guest starring credits include notable appearances on Out of Practice and Miss Match, opposite Alicia Silverstone.
Olson's breakout role came when she starred as "Sweet Dee" on the FX sitcom It's Always Sunny in Philadelphia, a character that has become iconic in contemporary television.