After college, Gordon moved to New York City and started his career as a comedy writer on the ABC late night variety show Fridays in the early 1980s. He became an independent filmmaker, writing and directing the Academy Award-winning short Ray's Male Heterosexual Dance Hall (1987) and the feature film Pie in the Sky starring Anne Heche, John Goodman, and Josh Charles. He also directed the feature film Career Opportunities.
Gordon has directed episodes on such TV series as Grace and Frankie, The Office, Weeds, Studio 60 on the Sunset Strip, The West Wing, Ally McBeal, Boston Public, Sports Night (also starring Josh Charles), Curb Your Enthusiasm (created, written by and starring Larry David, Gordon's co-worker on Fridays), Freaks and Geeks and The Wonder Years.
He has directed numerous television pilots -- among them One Tree Hill -- setting the look and design for the series. He directed and produced the TBS pilot The Wedding Band that premiered in 2012. Also in 2012, he directed the 30 for 30 documentary short for ESPN, "The Arnold Palmer", which was nominated for a Sports Emmy for Outstanding New Approaches Sports Programming in 2013.
Gordon has been nominated three times for the Directors Guild of America Award. In 2002, he received its Award for Outstanding Directing for a Comedy Series.