After moving to Los Angeles, Olson became a member of theater comedy troupe
The Groundlings Sunday Company. She trained with Sunday Company for a year, which led to her receiving a recurring role on
Curb Your Enthusiasm. In 2000, Olson made her debut television appearance in the
HBO comedy series
Curb Your Enthusiasm as Becky,
Cheryl Hines's sister. The same year as her television debut, Olson also had a minor role in the film
Coyote Ugly. She received more regular work after being cast on
The Drew Carey Show.
Carey would end up working closely with Olson, stating he knew she was "headed for stardom." He later cast Olson in the
Green Screen Show. She also toured
Bosnia,
Kosovo and
Norway with Carey and several other comedians, providing entertainment for US military troops through the
USO. She went on to make guest appearances in several television series, including ''
Punk'd (2003), Miss Match (2003), George Lopez (2004), and Out of Practice'' (2006). She garnered critical acclaim for her performance, with particular praise for her physical comedy. In 2007, Olson played a recurring role as Hartley Underwood, the "one-armed" neighbor in the FX drama series
The Riches. She had voice roles in numerous animated series, including
Family Guy (2009–2011),
Brickleberry (2012), ''
Bob's Burgers (2015–2019), and The Simpsons (2016). She also had roles in the comedy film Weather Girl (2009), the romantic comedy film Leap Year (2010), and the animated film Escape from Planet Earth (2013). In the action comedy film The Heat'' (2013), Olson appeared as a
Bulgarian drug addict who engages in an exchange of cultural perspectives (and insults) with
Melissa McCarthy's character. She also appeared as an Arizona cop in the road comedy film
Vacation (2015). In 2016, Olson provided the voice of Destiny, a nearsighted whale shark, in
Disney's animated sequel film
Finding Dory. Olson then starred as Mackenzie "Mickey" Molng in the
Fox sitcom
The Mick, which premiered in January 2017. She also served as an executive producer for the series. The second season of
The Mick premiered in September 2017. Fox canceled the series after the season ended in April 2018. For her performance in the series, she received two nominations for the
Primetime Emmy Award for Outstanding Guest Actress in a Comedy Series, had a voice role in the Netflix animated series
Agent Elvis and starred in the sports comedy-drama film
Champions. The next year, she appeared in the teen comedy film
Incoming. Olson took the leading-star role as the character Morgan Gillory in the
ABC crime drama series
High Potential in 2024, a remake of the French-Belgian series
HPI. She also guest starred as Deandra "Sweet Dee" Reynolds in the ABC sitcom
Abbott Elementary. ==Personal life==