Peter Cattaneo's Lucky Break is a likable comedy that suffered by being compared with his earlier hit The Full Monty, but is attractive enough in its own right. Charming, incompetent bank robber Jimmy Hands (James Nesbitt), five years into a 12-year sentence, puts together an escape plan that exploits the desire of the stage-struck prison governor (Christopher Plummer) to see his musical about the life of Nelson performed. The plan gets ever more complicated as he finds himself wanting to wreck the career of a bullying prison officer, trying to outwit an unpleasant thug who wants to supplant his original accomplices, and weighing the idea of escape at all against his growing relationship with anger-management trainer Annabel (Olivia Williams).
This is an intelligent caper film with some underlying serious tones. Jimmy slowly comes to realize that crime involves mixing with some unpleasant people. The backstage musical stuff--with its wonderfully fatuous ex-Cambridge director and a score just the right side of dreadful--is hilarious, and the plot's convoluted central scam is efficient as it plays out. If there is an overall failure, it comes from the clash between the film's farcical elements and the bittersweet quality of its central relationship, as well as Timothy Spall's portrayal of the victimized Cliff.