Diggs received the Bachelor of Fine Arts degree in musical theater from Syracuse University. Diggs' debut was in the ensemble cast of the 5-period Tony Award-winning musical Carousel. Withinside 1996, he had his large break, originating a role of the awful landlord Benny in Jonathan Larson's Tony Award- and Pulitzer Prize-winning Rent.

Diggs so moved from either stage to television, by owning the role on the soap opera Guiding Light. Within 1998, he made his film debut inside How Stella Got Her Groove Back. A charted month he accepted roles as a tantric sex god in Doug Liman's Go. Audiences may next understand him as an AWOL groom in the coming-of-age drama The Wood. Malcolm D. Lee's The Best Man features Diggs as the titular best man suffering from his own pre-wedding jitters. He as well starred in the remaking of William Castle's The House on Haunted Hill.

Diggs portrays a title character on the UPN television series Kevin Hill and can next exist as seen in the picture show adaptation of the musical Rent.

Within 2003, Diggs was on ''Punk'd after being tricked by Ashton Kutcher or his crew members, while his body is being inspected at a Punk'd-operated hospital.

Filmography
Rent (2005) .... Benjamin "Benny" Casket III Kevin Hill (2004) TV Series .... Kevin Hill Drum (2004) .... Henry Nxumalo Punk'd (2003) TV Series (one episode) .... Himself Malibu's Most Wanted (2003) .... Sean Basic (2003) .... Pike Chicago (2002) .... A Bandleader Equilibrium (2002) .... Brandt Brown Sugar'' (2002) .... Andre Romulus 'Dre' EllisDre Cross the Line (2002) .... Jamal Boy Just a Kiss (2002) (uncredited) .... Andre New Best Friend (2002) .... Artie Bonner Ally McBeal (1997) (TV) .... Jackson Duper (2001) Way of the Gun, The (2000) .... Jeffers House on Haunted Hill (1999) .... Eddie Baker The Best Man (1999/I) .... Harpist Stewart The Wood (1999) .... Roland Go (1999) .... Marcus How Stella Got Her Groove Back (1998) .... Winston Shakespeare