He is best known for his work as Lucifer in Supernatural, Paul Bennett in Dexter, Jacob in Lost, James Bishop in Being Human, Clayton Haas in Quantico, Joe Messing in Mulholland Drive, and Deputy Bill Standall in 13 Reasons Why.

He saw an advertisement for a modeling agency at a place called John Roberts Powers, where he received some free training.

Before the COVID-19 pandemic, he asked fans of TV show Supernatural on Twitter (now named X)[7] if they would be interested in finding his real father.

Some of his earlier television appearances are also in Northern Exposure, Tales from the Crypt, ER, Without a Trace, NYPD Blue, CSI: Crime Scene Investigation, Hunter, and The Commish.

In 1998, he played the Blonde Treehorn Thug who stuffs The Dude's head down the toilet and drops his bowling ball, breaking the floor tile, in the cult film The Big Lebowski.

In March 2009, he was cast on the ABC series Lost for an appearance in the final 2 episodes of Season 5, to play the role of the mysterious Jacob.

[12] In 2011, he and Curtis Armstrong, who played Metatron on Supernatural, guest starred alongside each other as well as their characters being enemy lawyers in season 7 of The Closer.

[13] In 2018, he voiced and motion captured his first video game role as antagonist Jacob Seed in one Ubisoft's Far Cry 5.

In 2021 and 2024, he played Virgil Poe in the American Rust TV series, a show based on the novel of the same name written by Philipp Meyer.

In July 2024, he appeared in Beverly Hills Cop: Axel F as one of Captain Cade Grant's, played by Kevin Bacon, main man antagonist named Beck.

The first one is through an affiliation with the Ayn Rand Centre UK,[21] and the second is to his own account with a series he has created called: Reality Checks, which are videos of ideas based on philosophical topics of everyday life.