acclaim and exposure. The following year, he played a tantric sex god in Doug Liman's Go, and AWOL groom in the coming-of-age drama The Wood alongside Omar Epps. 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). He also starred in the 1999 remake of William Castle's House on Haunted Hill. 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 2005 Rent film. Diggs is featured on the following cast recordings: Carousel 1994 revival cast; Rent 1996 original Broadway cast; The Wild Party original off-Broadway cast. He also sings on the Rent film soundtrack. In 2002, he reprised his role as the Bandleader in the film adaptation of Chicago, and also played opposite Christian Bale as Bale's partner/antagonist Brandt in the dystopian sci-fi thriller Equilibrium. In 2003, 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 early 2006, Diggs guest-starred for several episodes as Will Truman's love interest, James, on the eighth season of Will & Grace. 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 2006, 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. He was seen opposite James McDaniel in Charles Fuller's A Soldier's Play at Second Stage Theatre in New York. 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 2007 until 2013. Diggs had a guest role on The West Wing as a Secret Service agent in charge of the security detail for the President's daughter. He then guest-starred on Grey's Anatomy