When he was a child, his mother married Jeffries Diggs, whose surname Taye took. After Rent , he appeared as Mr. Diggs then moved from stage to television with a role on the soap opera Guiding Light. Malcolm D. Lee 's The Best Man features Diggs as the title character, an author and best friend of the groom portrayed by Morris Chestnut.
Diggs was featured in an episode of America's Next Top Model helping the contestants through an acting challenge.
Another notable role of his was on the comedy-drama Ally McBeal as a lawyer named Jackson Duper who was the love interest of the character Renee Raddick and the possible love interest of the Ling Woo character. Diggs portrayed the title character on the short-lived UPN television series Kevin Hill which despite critical acclaim was not renewed for a second season. He reprised the role of Benny for the Rent film.
Diggs is featured on the following cast recordings : Carousel revival cast; Rent original Broadway cast; The Wild Party original off-Broadway cast. He also sings on the Rent film soundtrack. In , Diggs appeared on the TV show Punk'd after being tricked by Ashton Kutcher , while getting a check-up at a Punk'd -operated doctor's office.
In May, ABC picked up his pilot, Day Break , in which he portrayed a detective trapped in the same day and forced to relive it to clear his name of murder; the show debuted in mid-November , but was abruptly canceled due to poor ratings. Although his film and television career continue to move forward, he still returns to the stage frequently. Diggs co-starred as Sam Bennett opposite Kate Walsh in Private Practice , the spin-off of Grey's Anatomy , which ran for six seasons from until Diggs had a major role in the live action adaptation of the comic Dylan Dog: Dead of Night Diggs is one of the stars of the independent film drama Between Us that won the grand jury prize at the Bahamas International Film Festival among its other festival appearances.
