What Could Have Been?: Chris welcomes Veep star Timothy Simons for a chat about a life-changing fork in the road moment that will forever tie the two performers together. Plus, viewers call in with personal stories to explore "what could have been."

Take a Chance: Special guests Tig Notaro and Patton Oswalt join Chris to encourage callers to do something risky. Plus, the show takes a huge chance by letting an at-home viewer be part of an unprecedented live television experiment.