Flanagan was born in Easterhouse, Glasgow, the second of four children. His sister Sue is a nurse at Queen Elizabeth Hospital in Glasgow.[1] He was an altar boy.[2][3]His facial scars are the result of a knife attack outside a nightclub where he had been working as a DJ. After leaving the club, he was attacked by a gang, stabbed and slashed with a knife, leaving him with the scars.[4]
Flanagan and his wife, Dina, have a daughter.[5] He was previously married to Rachel Flanagan and Jane Ford.
He portrayed arms dealer Gabriel Schector 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.[6] 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.
In July 2018, it was announced that Flanagan was cast in one of the main roles, Alec McCullough, on the Netflix series Wu Assassins.[7]