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Frequently works with the Farrelly Brothers. Studied theater at Illinois Wesleyan University. A member of the Trinity Repertory Company in Rhode Island for fifteen years, he appeared in such 1970s and 1980s Trinity Repertory productions as "Brother to Dragons," "Of Mice and Men," "True West," "American Buffalo" and "Waiting for Godot"; directed such later productions as "Tartuffe," "The Glass Menagerie", "The Miser" and Shekspeare's "Macbeth" and "Twelfth Night"; and was the company's artistic director for four years. One of several Rhode Island residents who have made films for the Farrelly Brothers. In four of their pictures, Richard even bought a house down the street from the brothers' childhood home in Cumberland, Rhode Island. He attended school with Larry Shue and worked with James Pickering, according to an interview of February 20, 2009. Pickering acted as the Nerd in Shue's famous play, "The Nerd," adapted as "Laus im Pelz (1987)". He worked as a summer truck driver for the father of actor John C. Reilly in Illinois. Jenkins coincidentally met Reilly when the latter was four years old. The two later worked together in Step Brothers (2008).