That world for Gale soon included performances in Cymbeline and The Misanthrope while he completed the Actor's Conservatory Program at A Noise Within theater company in Los Angeles. His other theater credits from that period include Miss Julie, Sweet Bird of Youth, Long Day's Journey Into Night, and The Importance of Being Ernest (see a more detailed list of Gale's acting credits below).

In 1997, Gale trained with Joan Scheckel, who started her public life as an actor and performer in New York’s avant-garde scene. In the mid-nineties she started running workshops for actors and directors and found herself much in demand in Hollywood and Los Angeles. The workshops in which Gale participated are reportedly quite intense, and stir up a lot of real emotion for everyone involved. Describing Joan Scheckel, actor Billy Cruddup says, "She thinks like an artist, but she's rigorous - coaxing people to go beyond what they already know. She's also playful (which is important) and her perceptions verge on the psychic."

Long before Gale joined the cast of Queer As Folk and embraced Showtime's "No Limits" philosophy, he was pushing the boundaries with projects to which he attached himself. In 1998, he performed as La Turista (the tourist) in "The Indian Queen", a 17th century British baroque opera. The text was filled with outrageous racist stereotypes and Eurocentric constructions of otherness. About the opening night performance, an LA Times reviewer wrote, "There is something in The Indian Queen to offend just about everyone. There is also something in it that should delight and astonish just about everyone as well. It's a mess. But it's a dazzling mess. It utterly, totally, unapologetically undoes just about everything its authors, composer Henry Purcell and poet John Dryden, set out to do in 1695. But it saves a work that probably could survive in no other reasonable way. It brings something new to opera at a time when you might think just about everything imaginable has already been done." [source: The first, the last, the only "Lowrider Spanglish Opera"]

Gale made his feature film debut as the nerdy but endearing "Booker" in Paul Scheuring's 36K, and appeared briefly in Lori Silverbush’s Mental Hygiene. In 2001, he filmed Wake, directed by Roy Finch. In 2002, Gale worked on an independent film titled "Rhinoceros Eyes" directed by newcomer Aaron Woodley, in which he played a detective. He also starred in another indie film called "Particles of Truth" with Jennifer Elster. In the Spring of 2004 Gale worked with Ms. Elster and her husband, Lewis Helfer, on another film called "Life on the Ledge (2004)," a dark comedy filmed in NYC, in which he plays a gangster.

Also in 2004, Gale worked on a three-part movie for Showtime called "Fathers and Sons" which was screened at the Sarasota Film Festival in January 2005. He starred in the movie "The Unseen," alongside Michelle Clunie ("Melanie Marcus" on QAF) which was filmed just outside of Atlanta, Georgia. Gale also starred in a film called "East Broadway" (formerly titled Social Grace, and re-titled yet again in early 2007 to Falling for Grace), directed by Fay Ann Lee who also has the female lead), filmed in NYC during the summer of 2004. Gale appeared in the CBS made-for-TV movie about Martha Stewart titled "Martha: Behind Bars", which aired in September 2005. In addition to a few guest appearances on "The Unit" (CBS) and "Deadwood" (HBO), Gale landed the lead role in "Vanished" on the FOX network. He appeared in the first seven episodes of the series.

Gale is the associate producer of the music documentary "Scott Walker: 30 Century Man," which premiered at the London Film Festival October 31, 2006.

During his hiatus from Queer As Folk in 2001, Harold played Josh in the off-Broadway play Uncle Bob, opposite George Morfogen. He enjoyed the role because the character of Josh was very different from the character of Brian Kinney. Gale returned to the New York stage in 2006 with a 3-month run off-Broadway in Tennessee Williams' Suddenly Last Summer at the Roundabout Theatre.