Gregg is also known for his role as FBI Special Agent Mike Casper on the NBC political drama series The West Wing (2001–2004) and as Richard, the ex-husband of Christine Campbell, in the CBS sitcom The New Adventures of Old Christine (2006–2010).
He wrote the horror film What Lies Beneath (2000) and wrote and directed the black comedy Choke (2008) and the comedy-drama Trust Me (2013). He appeared in the films The Adventures of Sebastian Cole (1998), One Hour Photo (2002), We Were Soldiers (2002), In Good Company (2004), When a Stranger Calls (2006), 500 Days of Summer (2009), Much Ado About Nothing (2012), The To Do List (2013), Labour Day (2013), Live by Night (2016), and Being the Ricardos (2021).
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