Darin Webb was born on August 7th 1987 in Fairfield, Iowa. His first experience improvising was onstage at Fort Smith, a musical comedy revue held in a barn-turned-theater near Ollie, IA, on his 11th birthday. In high school he was a nerd-lete, but was convinced to try out for the improvisation team for the IHSSA. Failing the group auditions, he joined as a solo improvisor. He performed solo, and acted as an understudy for the improv team his junior year. In his senior year, Darin made the group and performed with Chris Poole and Kristopher Johnson at the All-State Festival, winning the critics choice award for best group improvisation.
Darin attended Iowa State University in the fall of 2006. In the spring he joined Grandma Mojo's Moonshine Revival, ISU's resident improv troupe. He performed there for the semester before transferring to the University of Iowa. Darin promptly auditioned for Paperback Rhino and was a shoe-in.
Darin became a captain of Paperback Rhino after a year, and led the group with Joe Meyer for another two years. As captain he led the group in local performances as well as performances in Chicago, Minneapolis, and Fairfield, IA. He performed with the group opening for then-candidate Barack Obama at the US Cellular Center in Cedar Rapids, IA in 2007. Succeeding him as captains were Ben Mackey and Will Roberts.
Darin left Iowa City and moved to Gainesville, GA in the fall of 2010.