Attempting to track down a stolen Rembrandt, young insurance investigator Gin (Catherine Zeta-Jones) has her head turned by another artefact when she falls for elderly art thief Mac (Sean Connery), in this 1999 heist movie they should have called The Stomach-Churning Adventures of Mac & Gin.

Old man/young woman couples were rife in ’90s movies, but Entrapment‘s 39-year age gap makes everything else look like child’s play (which a lot of it technically was). For context Zeta-Jones was 30, and Connery was born in 1930, so at least they had some common ground. On some level the film knows it should ackowledge this, so it points out that Connery is 60 (which he isn’t) and has her do most of the pursuing. But he also keeps calling Gin a “good girl” and leering at her through binoculars, though in fairness that might have more to do with his eyesight.
Even if you can look past the weird Dracula romance (he lives in a castle by the way), narratively the film is all over the place. Its clumsy attempts to pull off the genre’s twists leave Entrapment with no real protagonist and character motivations that change in every scene, so you never know who you are meant to be rooting for or what they are trying to achieve. Gin’s characterisation is wildly inconsistent and sexist, repeatedly sabotaging missions she has been planning for years for the first old man she sees. In that sense it is like watching Point Break, except the closest it comes to an adrenaline rush is the constant risk that Mac stands up too quickly.
Despite her supposedly meticulous plotting, Gin’s plans (which include downloading $8 billion from a computer in Kuala Lumpur) are consistently altered by happenstance, or by Mac making decisions, or the arrival of her colleagues from the insurance firm, who run around Malaysia with guns in the absence of any state-sanctioned law enforcement. Of course heist flicks can benefit from daft storylines if the delivery is stylish or sexy enough, but here the only thing bigger than the plot holes is the age gap, resulting in a creepy caper that puts the nonce in nonsense.