Diamantopoulos began appearing in TV commercials and professional theatre productions at the age of 9, and by the time he turned 18, he had left home to partake in a series of U.S. national tours. A short time later, he landed on Broadway where he played leading parts in The Full Monty (2002) and Les Misérables (2003). Diamantopoulos attended East York Collegiate Institute.
He portrayed Robin Williams in Behind the Camera: The Unauthorized Story of Mork & Mindy. He has guest-starred in several series, including Kevin Hill, Charmed, The Sopranos, Nip/Tuck, and Boston Legal. In 2007, he appeared opposite Debra Messing in The Starter Wife, where he played the role of the gay interior decorator character of Rodney.
Diamantopoulos had a recurring role on State of Mind. He also guest-voiced on American Dad! in 2009.
On the eighth season of 24, he played US President Allison Taylor's Chief of Staff Rob Weiss. He played Frank Sinatra in The Kennedys. Diamantopoulos played Moe Howard in the 2012 The Three Stooges film. He also is the current spokesman for the firm Charles Schwab. He understudied Donny Osmond on tour of Joseph and the Amazing Technicolor Dreamcoat.
He had recurring roles on the NBC sitcoms Up All Night, as Maya Rudolph's on and off lover, Julian, The Office, as Brian, a former member of the show's documentary film crew, and on Arrested Development, as Marky, Lindsay's face-blind environmentalist boyfriend. He is also the voice of Mickey Mouse for the eponymous animated series.
Diamantopoulos grew up splitting time between Canada and Greece. He is of Greek descent and adheres to the Orthodox Christian faith. He met his wife, actress Becki Newton, in a subway station in New York. The couple married on May 12, 2005. Becki gave birth to their first child, a boy, in November 2010.
- The Adulterer (2000)
- Drop Dead Roses (2001)
- Law & Order (2002, TV series)
- Third Watch (2003, TV series)
- Frasier (2004, TV series)
- Nip/Tuck (2004, TV series)
- Charmed (2004, TV series)
- American Dreams (2004, TV series)
- Kevin Hill (2004, TV series)
- Jake in Progress (2005, TV series)
- Behind the Camera: The Unauthorized Story of Mork & Mindy (2005, TV)
- The Sopranos (2006, TV series)
- Wedding Daze (2006)
- Boston Legal (2006, TV series)
- Three Days to Vegas (2007)
- Raines (2007, TV series)
- The Starter Wife (2007, TV miniseries)
- State of Mind (2007, TV series)
- 24 (2010, TV series)
- The Kennedys (2011, TV miniseries)
- Up All Night (2011–2012, TV series)
- The Three Stooges (2012)
- Community (2013, TV series)
- The Office (2013, TV series)
- Arrested Development (2013, TV series)
- Family Guy (2013, TV series)
- American Dad! (2013, TV series)
- Mickey Mouse (2013–present, TV series)
- Episodes (2014, TV series)
- Hannibal (2014, TV series)
- Ernest: The Movie (2015)
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