Kaitlin Willow Olson worked on stage with ‘The Groundling’ before appearing in minor roles in movies ‘Eyes to Heaven,’ ‘Jacks,’ and ‘Coyote Ugly.’
After featuring in various episodes of ‘Curb Your Enthusiasm’ (2000-2020), ‘The Drew Carey Show’ (2002-2004) and ‘Punk’d’ (2003), Olson appeared in the series ‘Meet the Marks’ (2002), and played different roles in ‘Kelsey Grammer Presents: The Sketch Show’ (2005).
Olson received a major break as ‘Deandra ‘Sweet Dee’ Reynolds’ in the popular sitcom ‘It’s Always Sunny in Philadelphia’ (2005-present). After a recurring role in the TV-series ‘The Riches’ (2007-2008), she appeared in the romantic-comedy film ‘Leap Year’ (2010), the action-comedy ‘The Heat’ (2013), and ‘Vacation’ (2015).
Olson provided voice for various projects, including TV-series ‘Family Guy’ (2011), ‘Brickeberry’ (2012), ‘Unsupervised’ (2012), computer-animated sci-fi film ‘Escape from Planet Earth’ (2012), and Disney’s ‘Finding Dory’ (2016).
Olson was also the executive producer–star of the sitcom ‘The Mick’ (2017-2018). She starred in the dark comedy-thriller ‘Arizona’ (2018), and earned nomination for the comedy-series ‘Flipped’ (2020). She plays a recurring role in the comedy-drama streaming TV-series ‘Hacks’ (2021).