Welcome to The Second City Archives, in which we post an exclusive clip each week of some of comedy’s biggest superstars performing early in their careers on the legendary Chicago stage. Second City has generously given us a glimpse into their extensive archive of live performances, and over the coming weeks we’ll be sharing some rare and retro comedy never before seen on the web.
This week’s clip is from Second City Chicago’s 2008 revue America: All Better! featuring ensemble performers Lauren Ash, Joe Canale, Shelly Gossman, Anthony LeBlanc, Brad Morris, Mike O’Brien, and Emily Wilson. In the above clip, O’Brien – who joined the Saturday Night Live writing staff just a year later – leads an old-timey saloon sketch, only to sabotage it all in the name of love. Unfortunately for O’Brien, things don’t exactly go the way he hoped they would.