Middleton was the Chief Instructor on "SAS: Who Dares Wins", a reality quasi-military training television programme produced by Channel 4, which was first broadcast in 2015. The show propelled Middleton into celebrity limelight. "Mutiny", an adventure/reality crossover show, screened on UK television in February 2017, with Middleton starring as boat captain alongside eight volunteering participants. The show was a re-enactment of the infamous Mutiny on the Bounty and Middleton described the experience as "mentally speaking, the hardest thing I've ever done". In March 2021, Middleton was dropped by Channel 4 over his personal conduct.