Livingston's other roles include the films Swingers (1996), Adaptation (2002), The Conjuring (2013), James White (2015), Tully (2018); and the television series Loudermilk (2017–2020), and Boardwalk Empire (2013).

Both his sister, Jennifer Livingston, and brother-in-law, Mike Thompson, were TV news personalities at WKBT-DT in La Crosse, Wisconsin.

In 1999, he starred as the male lead, Peter Gibbons, in the comedy cult classic Office Space, which co-starred Jennifer Aniston and was written and directed by Mike Judge.

Livingston widened his variety of roles when he played a Hollywood agent in Adaptation (2002), a weaselly Ivy League upstart opposite Alec Baldwin's casino boss in The Cooler (2003) and teachers in Winter Solstice and Pretty Persuasion (both in 2005).

In 2006, he starred as FBI negotiator Matt Flannery in the Fox series Standoff, co-starring Rosemarie DeWitt, and he was an advertising spokesman for Sprint Nextel.

[11] In 2013, Livingston co-starred in the indie comedy Drinking Buddies alongside Olivia Wilde, Jake Johnson and Anna Kendrick.

Livingston played the title role of Sam Loudermilk, a former music critic and recovering alcoholic who works as a substance abuse counsellor and support group leader, and who regularly doles out clever but acid-tongued critiques to his clients, his friends, and random people he encounters.

[14][15] Livingston also appears in the ABC drama A Million Little Things as Jon Dixon, whose suicide causes his group of friends to evaluate their own lives.