His first television roles were in
Screen One (1992) and
Taggart (1993). Flanagan worked in
Robert Carlyle's
Raindog Theatre for three years before being cast in
Braveheart (1995). He has had roles in
Face/Off (1997),
The Game (1997),
Sunset Strip (2000),
Gladiator (2000),
All About the Benjamins (2002), ''
Charlie's Angels: Full Throttle (2003), Alien vs. Predator (2004), Sin City (2005), Smokin' Aces (2006), When a Stranger Calls (2006), The Last Drop (2006), Smokin' Aces 2: Assassins' Ball (2010), Guardians of the Galaxy Vol. 2 (2017) and the TV mini-series Attila''. He portrayed
arms dealer Gabriel Schector in the first episode of
24s 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. Flanagan played McCullough on the
Netflix series
Wu Assassins which ran for one season, and as Walter Flynn in the Starz series
Power Book IV: Force. ==Personal life==