Rise to Success: Career Highlights of Kaitlin Olson

By Popular Timelines Editorial Team · Updated: July 10, 2025

How Kaitlin Olson built a successful career. Explore key moments that defined the journey.

Kaitlin Olson is an American actress and comedienne recognized primarily for her role as Deandra "Sweet Dee" Reynolds in the long-running FX comedy series *It's Always Sunny in Philadelphia*. Beyond this iconic role, she currently stars as Morgan Gillory in the ABC crime drama series *High Potential*. Olson has built a successful career through comedic and dramatic roles, establishing herself as a prominent figure in the entertainment industry.

Sections (2)

Full Timeline Career & Achievements

2000: Television debut in Curb Your Enthusiasm and role in Coyote Ugly

In 2000, Kaitlin Olson made her debut television appearance in the HBO comedy series Curb Your Enthusiasm as Becky. She also had a minor role in the film Coyote Ugly.

Loading Video...

2000: Recurring role in Curb Your Enthusiasm

In 2000, Kaitlin Olson portrayed Becky in the HBO sitcom Curb Your Enthusiasm.

Loading Video...

2002: Guest appearance in The Drew Carey Show

From 2002 to 2004, Kaitlin Olson made guest appearances in several television series, including The Drew Carey Show.

Loading Video...

2003: Guest appearance in Punk'd and Miss Match

In 2003, Kaitlin Olson made guest appearances in several television series, including Punk'd and Miss Match.

Loading Video...

2004: Guest appearance in George Lopez

From 2002 to 2004, Kaitlin Olson made guest appearances in several television series, including George Lopez.

Loading Video...

2005: Stars in It's Always Sunny in Philadelphia

In 2005, Kaitlin Olson began starring as Deandra "Sweet Dee" Reynolds in the FX comedy series It's Always Sunny in Philadelphia.

Loading Video...

2006: Guest appearance in Out of Practice

In 2006, Kaitlin Olson made guest appearances in several television series, including Out of Practice.

Loading Video...

2007: Recurring role in The Riches

In 2007, Kaitlin Olson played a recurring role as Hartley Underwood in the FX drama series The Riches.

Loading Video...

2009: Voice role in Family Guy and role in Weather Girl

In 2009, Kaitlin Olson had voice roles in Family Guy. She also had roles in the comedy film Weather Girl.

Loading Video...

2010: Appeared in Leap Year

In 2010, Kaitlin Olson appeared in the comedy film Leap Year.

Loading Video...

2012: Voice role in Brickleberry

In 2012, Kaitlin Olson had a voice role in Brickleberry.

Loading Video...

2013: Appeared in The Heat

In 2013, Kaitlin Olson appeared in the comedy film The Heat.

Loading Video...

2013: Appeared in Escape from Planet Earth and The Heat

In 2013, Kaitlin Olson had roles in the animated film Escape from Planet Earth and the action comedy film The Heat.

Loading Video...

2015: Voice role in Bob's Burgers and role in Vacation

In 2015, Kaitlin Olson had voice roles in Bob's Burgers. She also appeared as an Arizona cop in the road comedy film Vacation.

Loading Video...

June 2016: Tribute to Orlando Nightclub Shooting Victims

In June 2016, Kaitlin Olson and others narrated the stories of the victims of the Orlando nightclub shooting in a video released by the Human Rights Campaign.

2016: Appeared in Finding Dory

In 2016, Kaitlin Olson appeared in Finding Dory.

Loading Video...

2016: Voice role in The Simpsons

In 2016, Kaitlin Olson had a voice role in The Simpsons.

Loading Video...

January 2017: Starred in and Executive Produced The Mick

In January 2017, Kaitlin Olson starred as Mackenzie "Mickey" Molng in the Fox sitcom The Mick, also serving as an executive producer for the series.

Loading Video...

September 2017: The Mick Season Two Premiered

In September 2017, the second season of The Mick premiered.

Loading Video...

2017: Lead role in The Mick

In 2017, Kaitlin Olson played Mackenzie "Mickey" Molng, the lead role in the Fox comedy series The Mick.

Loading Video...

2018: Appeared in Arizona

In 2018, Kaitlin Olson appeared in the dark comedy thriller film Arizona.

Loading Video...

2020: Appeared in Space Force and Flipped

In 2020, Kaitlin Olson guest starred in the Netflix workplace comedy series Space Force and starred as Cricket Melfi in the Quibi comedy series Flipped.

Loading Video...