A house team at ImprovOlympic in Chicago formed in 1993 where they performed their own musical form, the Drake. Their name was inspired by the title of a gay porn video one of the members found at a local JJ Peppers. Many of the players also performed in the original production of UCB's the Real Real World. In 1997, IV started performing at the Playground Theater.
The original cast included Jeff Ahern, Jeff Clampitt, Andy Cobb, Tina Fey, Ross Foti, Martín Gobbée, Mike Meiners Amy Poehler, Kevin Reome. Jim Jarvis and Charles Glen were added after the first show.