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Ryan was born in Indiana and graduated from Indiana University, Bloomington, where he minored in Theatre. After school, Ryan headed to Chicago where he did plays and studied at The Second City. In Chicago and later in Los Angeles, he began writing and performing comedic solo shows. Ryan studied with John Kirby at JK Studios in Hollywood, where he met his longtime collaborators who eventually formed Nowadays Pictures, where Ryan works as a actor, writer and producer. Ryan has written several screenplays and co-wrote Under the Hollywood Sign, which won the Best Feature Film of Merit Award at The Catalina Film Festival.