He is known for playing Jerry Best in the Fox sitcom The Bernie Mac Show (2002–2005), Chase Chapman in the ABC comedy series Samantha Who?

[3] He graduated from The Wheatley School in Old Westbury, New York, before attending the University of Arizona, majoring in theater arts.

He had some other small roles until he received a main role as Freddie Sacker on Darren Star's short-lived Wall Street series The $treet[4] in 2000, which was pulled from the airwaves after seven episodes, but which allowed him to quit his job waiting tables and move back to New York.

His subsequent TV roles included Terry Loomis on the short-lived Steven Bochco law drama Philly[5] in 2001–2002, Jerry Best in The Bernie Mac Show (2002–2005),[6] Patrick Van Dorn on the John Stamos comedy Jake in Progress (2004–2005)[6] and Chase Chapman on the ABC comedy Samantha Who?

In 2011, he landed a starring role as Louis Litt in the USA Network series Suits, which ran until 2019.