Kaitlin Olson

Kaitlin Olson is an actress best known for playing Sweet Dee on FX’s It’s Always Sunny in Philadelphia. She began her acting career at the Groundlings Theater, securing a much desired role as part of the Sunday Company. Kaitlin has shown off her sketch and improv training with shows like Punk’d, The Jamie Kennedy Experiment, and Kelsey Grammar Presents: The Sketch Show. Fun Fact: Kaitlin was one of the stars of The Sklar Brother’s web series Held Up.

Guest Appearances

March 18, 2019

The Boys help KAITLIN OLSON figure out what she’s doing next.

This episode is sponsored by Squarespace (www.squarespace.com/THEBOYS code: THEBOYS), Brilliant Earth (www.brilliantearth.com/THEBOYS), Harry’s (www.harrys.com/HANDBOOK), and Robinhood (www.HANDBOOK.robinhood.com).

July 15, 2018

Paul F. Tompkins welcomes listeners right under the wire to Spontaneanation! This time out, Paul’s special return guest is Kaitlin Olson of It’s Always Sunny In Philadelphia and The Mick! Kaitlin chats about what her spirit animal would be if she has met or seen it before, the biggest person who has hugged her in her adult life, and her favorite animal as a child. Then, they are joined by improvisers Carl Tart, Jean Villepique, and Marc Evan Jackson, to improvise a story set Backstage at an Adult Community Center Talent Show. And as always, Eban (only the best) Schletter scores it all on piano!

April 27, 2018

Casey, Danielle and April open the live show wearing their best Ramona, Sonja and Dorinda from the Halloween show. They are joined by the HILARIOUS AND GIFTED Kaitlin Olson (moonlighting as Carole/Amelia E.). Kaitlin performs a Dorinda for the ages that should win a goddamn Oscar or Nobel Peace Prize. 

This episode is brought to you by Box of Style (www.boxofstyle.com/BitchSesh), Leesa (www.leesa.com//HOUSEWIVES), Lola (www.mylola.com code: HOUSEWIVES40), and BioClarity (www.bioclarity.com code: HOUSEWIVES).

January 27, 2017

Actress Kaitlin Olsen joins Randy and Jason this week to talk about getting cast in FOX’s “The Mick,” dealing with a household full of boys, and appearing on Curb Your Enthusiasm. Plus, Kaitlin shares her top bits from It’s Always Sunny in Philadelphia, and the Sklars give Ozzie Guillen a call to get his take on the recent Hall of Fame announcements.


This episode is sponsored by ZipRecruiter (www.ziprecruiter.com/happy).

May 11, 2015

Paul F. Tompkins welcomes adults and children of all genders but NOT pets to Spontaneanation! This week he is joined by special guest Kaitlin Olson of It’s Always Sunny in Philadelphia! They chat about Kaitlin’s favorite invention, changing into soft clothes at home, and the unusual trick-or-treating arrangement on the Olson ancestral home. Paul is then joined by improvisers Mark McConville, Chris Tallman and Jean Villepique, to improvise a story set at a UFC Weigh-In. As always, the astonishing Eban Schletter scores it all on piano. Will Crusher Emily, the Sausage Maker from the Cuyahoga defeat Monster (not Demon) Brad? Tune in to find out!

Los Angeles: Spontaneanation will be LIVE in front of your very eyes with special guests on Friday, June 19th at Largo at the Coronet! Get tickets now at http://www.largo-la.com/!

December 17, 2010

It’s always sunny in Sklarbro Country when Owen “The Butterscotch Stallion” Wilson and Kaitlin Olson (The Butterscotch Philly, of course) drop by. Kaitlin regales us with the joys of motherhood and the well-kept state of the Earwolf bathroom before she and The Sklars launch into some longer-than-usual hits about Shaq, Baron Davis, and Cliff Lee’s wife. Owen gives us some insight on his recovery from depression as well as the affair he probably had with Sheryl (Cheryl? Sharrel?) Crow. Leave us your best D.J. names for Rony Seikaly and join the rest of the Sklarmy over at Prediculous. Amber Alert!