Ross, who grew up in Wantagh, NY, had appeared only a handful of times onscreen when he was cast on “30 Rock.” One of his only roles was a bit part in an episode of “The Upright Citizens Brigade” (Comedy Central, 1998-2000), a sketch and improv comedy show co-created by and featuring such comedy luminaries as Amy Poehler. While honing his onstage comedy skills, Ross held a series of production jobs. Among his first was a stint as a network page on “Late Night with Conan O’Brien” (NBC, 1993- ). He also worked as a member of the production staff for “Sex in the City” (HBO, 1998-2004); as a writer’s assistant on the sitcom, “Ed” (NBC, 2000-04); and as an assistant talent coordinator on the comedy talk show, “Tough Crowd with Colin Quinn” (Comedy Central, 2002-04). One of his first forays into performance side was voicing a character for the controversial video game, “Grand Theft Auto.”
Ross soon landed his big break on “30 Rock,” which debuted to high critical acclaim but dismal ratings in the fall of 2006. Set behind the scenes of the fictional sketch comedy show, “TGS with Tracy Jordan,” the series was based on creator and star Tina Fey’s experiences as head writer on “Saturday Night Live” (NBC, 1975- ). Ross won the regular role of Josh Girard, the only male cast member of the female-centered comedy show, “The Girlie Show,” renamed when troubled comic actor Tracy Jordan (Tracy Morgan) joins the show to boost ratings among male viewers. It was easy to see that Ross may have been cast in part because of his passing resemblance to “S.N.L.” star and Fey’s co-anchor of “Weekend Update,” Jimmy Fallon.
While Ross was low on the acting totem pole, his small supporting role connected with viewers from the start, thanks to his dead-on impressions of Ray Romano and Jay Leno. Ironically, there was a running gag that his impressions were often unappreciated by writers and producers on the show, and that Josh may have owed his song and dance skills to the fact that his parents raised him as a girl for the first several years of his life. Despite his limited previous exposure, Ross shared plenty of screen time with stars Morgan and Baldwin – particularly in a memorable episode in which he gets in trouble by imitating the latter’s voice with pitch-perfect accuracy.
As his recognition grew, fans of Ross sought out his appearances in comedy shorts online, most notably “Johnny & Wade,” which he made with friends and fellow comic performers, Joe D. and Adam Wade. He also appeared in online comedy shorts such as “The Tribe,” a prehistoric version of the NBC hit, “The Office” (NBC, 2005- ), which ran on the website for the comedy troupe, Channel 102. To balance his TV work, Ross moved to features, appearing in the noir comedy, “Watching the Detectives” (2007) and in the Dane Cook-Jessica Alba romantic comedy, “Good Luck Chuck.” (2007).