Rachael Mason

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Rachael is a comedian, improvisor, and teacher. She has performed in many shows at The Annoyance Theatre, iO Theater, and The Second City in Chicago.


Rachael Mason began her career in improvisation at Skidmore College, home of the National College Comedy Festival, with the Ad-Liberal Artists. After graduating with a degree in English Literature, concentrating on Shakespearean Studies, she moved to Chicago to study improv with Del Close. She trained at iO, The Annoyance Theatre, and The Second City. Her credits include an almost 4 year stint with The Second City National Touring Company, “WWW.com All Over My Face”, “Big Trouble at Hairy Gulch”, “Donkey Improv”, and “Screw Puppies” at the Annoyance. At iO she has played with “The Armando Diaz Experience, Theatrical Movement and Hootenanny”, Monster Island, Jane, Preponderate, Genealogy, The Lindbergh Babies, Swanel, The Deltones, Baby Wants Candy, the iO Road Show Touring Company, and Children of a Lesser God. She was Director of the iO Training Center from 2005 to 2010. She has also been seen in ComedySportz’s The Hot Karl, Second City’s Jewsical the Musical, and The Second City Norwegian Dawn Cruise Cast. She is most happy when she is the friend in Susan Messing’s "Messing with a Friend" at The Annoyance.