David Kenyon Webster in the HBO miniseries Band of Brothers and appeared in the films Fight Club, Center Stage, Mindhunters, and Sexual Life.

He was seen in Center Stage,[3] Fight Club,[4] Catherine Jelski's The Young Unknowns, The Scoundrel's Wife,[5] Seven and a Match,[citation needed] Renny Harlin's Mindhunters for Miramax,[6] and the independent feature Sexual Life for director Ken Kwapis.

[13] In 2010, Bailey had a recurring role in USA Network's Covert Affairs as Ben Mercer, Annie's ex-boyfriend, who was being targeted by the CIA, before returning to the Agency near the end of Season 1.

[14] Bailey had a guest role on 30 Rock in 2011 as Anders, a love interest of Liz Lemon's who is "definitely not a Swiss prostitute that Martha Stewart recommended.

[16] On May 1, 2013, Bailey guest-starred in "Traumatic Wound" on Law & Order: Special Victims Unit as Frank Patterson, an Iraq war veteran with PTSD who becomes a key witness in an investigation of a sexual assault in a nightclub.