Havana

Havana (1990) is a Sydney Pollack romance you can watch online on iFILM. Professional card sharp Jack Weil sails to Cuba chasing one big poker score and lands in the capital just as the Batista regime crumbles, on the knife-edge of 1958 turning into 1959.

Jack trusts no one and bets only on himself. Then, on the ferry into Havana, he meets Roberta (Lena Olin), the wife of a revolutionary — and for once he stakes everything on a person instead of a hand. The old Cuba is coming apart around them: casinos, bribes, midnight arrests, a gathering underground. Robert Redford plays Weil, with Alan Arkin and Tomas Milian alongside and cinematographer Owen Roizman behind the lens.

This was the seventh and final pairing of Pollack and Redford, after The Way We Were and Out of Africa — a big, unhurried picture about love set against history, a flop on release that has aged into something quietly underrated. One for viewers who like old-fashioned romance and the mood of an era running out of time. Stream Havana (1990) online on iFILM.