Bob Oestrreich was born and raised in Duluth, MN. He has performed all throughout the Midwest. Bob’s fast-paced, witty, idiom heavy style has been described as a naïve psychopath in Mr. Rogers' neighborhood. He is  also the Winner of the House of Comedy Funniest Person with a Day Job 2023 and the Winner Minnesota’s Knock Out Comedy Competition.

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Over the years, Bob has worked with a number of comedians, including Dustin Diamond and Sean Donnelly. He has performed at number of venues, including Dubh Linn Brew Pub's Pro Comedy Tour and at the House of Comedy at the Mall of America.