Timothy, one of Chicago's well-known improvisers, creates Improvapalooza and Mary Beth hopes to help him grow the festival to international heights. Teams are given a suggestion of 'Chicago' at the beginning of the day and a film crew follows two main teams as they fumble to create a 20-minute show for audiences that night.
| Actor | Role |
|---|---|
 Vanessa BayerKate Clark | Kate Clark |
| RRay ChaoCharles Frank | Charles Frank |
| JJ.W. DeanHarold Ramis Jr. | Harold Ramis Jr. |
| JJeff GarretsonLee 'Shim' Beau | Lee 'Shim' Beau |
| MMatt GeilerRob Robinson | Rob Robinson |
| JJessica Noelle HardyKrystal Dennis | Krystal Dennis |
| BBenny HarrisLenny Ferris | Lenny Ferris |
| CCarrie LongLinda Anderson | Linda Anderson |
| EEileen MontelioneConnie McDonald | Connie McDonald |
 Michael PalascakTyler Jackson | Tyler Jackson |
| NNikki TaguilasImproviser | Improviser |