Can you believe Simon’s first movie role was back in 1997 with the Oscar-winning L.A. Confidential? While the film is now primarily remembered for a searing supporting turn from Kim Basinger, who won an Academy Award for her work, it gave Simon his first Hollywood break.

He plays Matt Reynolds, a dashing blonde actor who is struggling to find work and instead gets engaged in a set-up affair with Ron Rifkin’s Ellis Loew, although meets a tragic end soon after.

Arguably his most memorable big screen turn, in 2006, Simon played smooth-talking writer Christian Thompson in The Devil Wears Prada, who gives Anne Hathaway’s Andy that fateful Harry Potter manuscript, sleeps with her in Paris, and receives one of the most brutal break-up lines in aughts cinema (“I’m not your baby”). So far, it doesn’t look like Christian is slated to return in the classic’s upcoming sequel.

Simon was cast with a truly stacked ensemble for 2011’s Margin Call as Wall Street investment bank division head Jared Cohen. He stars in the film with Paul Bettany, Demi Moore, Jeremy Irons, Zachary Quinto, Penn Badgley, Mary McDonnell, Stanley Tucci and Kevin Spacey. He won an Independent Spirit Award as part of the ensemble, and the screenplay earned an Oscar nod.

From 2001-04, Simon played lawyer Nick Fallin in the CBS drama The Guardian, who is sentenced to community service due to drug-related convictions. The show centers on his relationship with his father, played by Dabney Coleman, and serves as Simon’s breakout performance. It also earned him his very first Golden Globe nomination in 2002.

From 2008 to 2015, Simon reigned as one of procedural television’s leading heartthrobs playing (phony) psychic medium Patrick Jane in CBS’ The Mentalist. The show was a ratings success, airing seven seasons and making Simon a household name, also earning him Golden Globe, Screen Actors Guild and Primetime Emmy nominations.