Gambit

Gambit (1966) is a clever heist comedy you can watch online on iFILM, directed by Ronald Neame. Michael Caine plays small-time thief Harry Dean, who sets out to steal a priceless bust from the richest man alive.

For the job he recruits a Hong Kong showgirl named Nicole, played by Shirley MacLaine. The film's first stretch lays out the robbery exactly as Harry imagines it — silent, flawless, every move on cue. Then reality arrives, the millionaire Shahbandar (Herbert Lom) refuses to play along, and the perfect scheme comes apart piece by piece.

That gap between the daydream heist and the messy real one became a trick dozens of caper films borrowed later. MacLaine spends much of the movie keeping a serene poker face, and half the fun is watching it crack. A 2012 remake with Colin Firth came and went; the 1966 original still has all the charm. Stream Gambit (1966) online on iFILM.