In 1994 Diggs made his very first appearance on Broadway in a production of Carousel, the famous musical from Oscar Hammerstein II and Richard Rodgers. After his work on the show, though, he then relocated to Japan some 12 months later, bagging a job at Tokyo Disneyland. During his time there, the aspiring performer continued to hone his skills.
After spending a few months in east Asia, Diggs eventually came back to New York in 1996, returning to Broadway later that year. He joined the cast of the Jonathan Larson musical Rent at that point, which kick-started his career in the world of entertainment. On that note, the New York resident enjoyed another significant moment over that period.
Indeed, Diggs made his television debut back in 1996 as he bagged a small role in New York Undercover. After his brief appearance in that show, he was then cast in an episode of Law & Order a short time later. Off the back of those performances, the actor continued to establish himself on the small screen in 1997.