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He moved to Los Angeles and was cast in supporting roles in Some Folks Call it a Sling Blade and The Low Life.
Livingston landed his first role in a major film in 1996's Swingers.
Going beyond nice-guy roles, Livingston played a Hollywood agent in Adaptation (2002); a weaselly Ivy League upstart to Alec Baldwin's casino boss in The Cooler (2003); and teachers in Winter Solstice and Pretty Persuasion (both 2005).
He also appeared as sardonic writer Jack Berger, Carrie's short-term boyfriend in the fifth and sixth seasons of Sex and the City.
In 2006, he starred as FBI negotiator Matt Flannery in the Fox series Standoff, co-starring Rosemarie De Witt, and he was an ad spokesman for Sprint Nextel.
In November 2007, the indie film Holly told the story of a Vietnamese girl trafficked into the sex trade in Cambodia.
Livingston starred as Patrick, a shady card shark who becomes determined to save Holly from her ill-destined fate.
Livingston was previously engaged to actress Lisa Sheridan but as we all know love happens when it is least expected.
Livingston and Sheridan broke up after they found that they are incompatible for each other.