He portrayed arms dealer Gabriel Schecter in the first episode of "24"s seventh season and appeared in the episode "Headlock" of "Lie to Me", aired in the U.S. on Monday 2 August 2010. He was one of the main cast members of "Sons of Anarchy", in which he plays an outlaw biker named Filip "Chibs" Telford. In October 2010, Flanagan was revealed as the spokesperson for the Scottish soft drink Irn-Bru. In July 2016, he appeared in the music video for the song "Rotting in Vain" by Korn.