McElhenney scored his first major role with a small part in "The Devil's Own", followed by small parts in "A Civil Action", "Wonder Boys", and "Thirteen Conversations About One Thing", though his role in "The Devil's Own" was cut out of the final edit. He later had more substantial parts in "Latter Days" and "The Tollbooth", and a small role in the "Law & Order" episode "Thrill". At the age of 21, a debut script by McElhenney was optioned with writer-director Paul Schrader attached to direct, before the project fell through after one year of edits and rewrites.