Connery performed many roles in theatre and subsequently had parts in several B-films. His film début was in The Lords of Discipline (1983). He appeared in the Doctor Who serial Vengeance on Varos in 1985; he also portrayed Robin Hood in the final series of the television series Robin of Sherwood in 1986.

He later portrayed James Bond creator Ian Fleming in the 1990 television drama Spymaker: The Secret Life of Ian Fleming. In 1997, he appeared in a fantasy film (originally intended as a pilot episode for a longer series); playing the title role of Merlin in Merlin: The Quest Begins, directed by David Winning. He appeared in Faithful Dealing (2001) in London, an English Restoration Whodunit, produced by Dominic Madden. In 2003, he toured with a stage production of The Blue Room. In 2004, he was a main character in the children’s show Shoebox Zoo and returned in the second series in September 2005.

Connery met American actress Mia Sara during the making of Bullet to Beijing in Russia. They married in 1996, and in June 1997 they had a son named Dashiell Quinn Connery. The couple divorced in 2002.

In 2008, he made his directorial début with the film Pandemic and in 2009 directed The Devil’s Tomb. Connery directed the 2011 “After Dark Originals” film 51, and The Philly Kid (2012) for the “After Dark Action” series.

In 2014, he took part in BBC One’s Celebrity MasterChef.

In 2016, Connery directed Tommy’s Honour, a film celebrating the lives of golf pioneers Old Tom Morris and Young Tom Morris. The film opened the 2016 Edinburgh International Film Festival on 15 June 2016, and won Best Feature Film at the 2016 British Academy Scotland Awards.