Jimmy Pennington

Jimmy Pennington moved to Chicago from Pennsylvania in 2006 to study and perform improvisation. Since then, he has had the opportunity to learn from some of Chicago’s smartest and funniest performers. After performing at iO for a few years, Jimmy was asked to understudy the incredible Annoyance production 40 Whacks, which lead to him joining the cast of CoEd Prison Sluts. Annoyance credits include Doublewide Lust, It’s Christmas Goddammit, Splatter Theater, Lonesome Drifter, The Annoyance Christmas Pageant, his autobiographical Jimmy of Nazareth, and many others. Jimmy is especially excited to show students the potential joy of improvising that comes from Annoyance’s particular style of performance; specifically the freedom from character co-dependency. Jimmy continues to perform at various theaters around Chicago, but will always consider The Annoyance his home.


Reviews of Jimmy Pennington:

AP5 Student

“Jimmy is the best teacher I’ve had. He has a strong artistic viewpoint, gives very insightful and personalized feedback, leads a very organized class, and gets us in tons of scenes so we get a lot of chances to work on our craft. He handles sensitive situations well and cultivates a safe class environment by calling out racist, misogynist, homophobic bullshit and challenging people to be more mindful about their choices.
I am going to name my first child Jimmy. “

AP5 Student

“Jimmy is the best teacher I’ve ever had in Chicago. He balances being a friend with being inspiring in such a great way. I grew so much as a performer. “

AP5 Student 

Jimmy is just the best.  I went through all of iO and now The Annoyance, and I think he might be my very favorite instructor. “

Currently Working On
Currently Performing In
Currently Teaching