His first film appearance was in the 1994 version of The Jungle Book. His first major cinema role was in Angela Pope's 1996 drama Hollow Reed, where he played a child abuser, followed by a main role in Guy Ritchie's popular 1998 London gangster film Lock, Stock and Two Smoking Barrels. Flemyng later claimed to have lost so much money while playing poker with the film's backers in between takes on set that he had to work on the four days of re-shoots the film required for no fee. He went on to appear in films such as The Red Violin and Deep Rising (1998), Snatch (2000), George A. Romero's Bruiser (2000) and Rock Star (2001). Flemyng also starred in the short film Feeling Good, written by Dexter Fletcher, whom he met while working on Lock, Stock and Two Smoking Barrels.