A dorky Jon Heder-type actor, Miles honed his stand-up skills on New York's alternative comedy scene. In the early '00s he began landing small TV and film roles, often working with his old scene cohorts, such as Stella's Michael Showalter, who penned him a part in Wet Hot American Summer. Miles also branched out into screenwriting and directing, helming a number of short films, including Ray Has Sex featuring him as a virginal ubernerd. In 2006 the goofy player landed his first series-regular role on Comedy Central's small-time newsroom mockumentary Dog Bites Man, as (what else?) a geeky production assistant.