As a seasoned character actor, Skip has played multiple roles appearing in Feature Films, National Commercials, Network TV series and A-List Artist Music Videos as well as Web Series. He has also worked as a featured character in various industrial and training videos.

Skip's characters include featured supporting role as an Italian Tailor in the upcoming comedy feature Stealing Pulp Fiction; Co-starring Jason Alexander and Cazzie David. As a Boxing Judge in Father Stu (Feature Film) with Mark Walberg and Mel Gibson, TV Executive on Lilly Singh's late night network talk show (Sketch comedy Universal/NBC), A Biker in Ed Sheeran's Music Video (Overpass Graffiti, A Motel Guest in Justin Bieber's Holy, and lead in a Warner sponsored Ed Sheeran video titled That's On Me. A featured Barber alongside Charles Barkley, Samuel L Jackson, Jennifer Garner, directed by Spike Lee in Capital One's National Commercial (Chuck Cuts) for the 2022 NCAA March Madness campaign.