Gregory made his professional debut in 2005 at Porthouse Theater as Riff in
West Side Story. During college, he also appeared as Ferdinand in
The Tempest for
Great Lakes Theater and its sister company,
Idaho Shakespeare Festival. David began a two-week stint on ABC's
One Life to Live in the summer of 2009. He was offered a contract that fall and stayed with the show until its cancellation. After
One Life to Live ended in 2012, Gregory guest-starred on multiple television series, including a season-long arc on the short-lived NBC series
Deception. In 2014, he appeared in Hartford Stage's
Vanya and Sonia and Masha and Spike, earning a Connecticut Critics Circle Award nomination and appearing on the cover of
American Theater magazine in the role the next year. Gregory's audio Western, "Powder Burns," won the
Voice Arts Award for Outstanding Storytelling/Best Performance for an episode dealing with Alzheimer's disease.
John Wesley Shipp and
Ed Asner starred opposite Gregory in the episode.
Western Writers of America hailed the production as "Darn Good Entertainment. The Future of Westerns." Gregory's play
Hank & Jim Build a Plane was workshopped at the
Last Frontier Theatre Conference in
Valdez, Alaska, and at
Le Petit Theatre du Vieux Carre in New Orleans. The drama follows
Henry Fonda and
James Stewart, best friends, movie stars, yet political opposites as they grapple with their differences on the night Henry's daughter Jane takes her famous trip to Vietnam. The play has been optioned by Tony Award-winning producers Jack W. Batman and Bruce Robert Harris at SunnySpot Productions in New York. In June 2023, Gregory starred as Juror #8 in a sold-out run of
Twelve Angry Men at The Powerhouse Theatre in New Canaan, Connecticut. == Personal life ==