Kino Lorber
Robert Redford returned to the screen after a four-year absence with this lush romantic thriller. He plays Jack Weil, an American gambler returning to Havana (where he keeps an apartment) on Christmas 1958 to play high-stakes poker with the biggest rollers on the island. Jack is an opportunist and a playboy who understands the ways of power and money but is utterly ignorant of the revolution in the countryside that has the police and the army on high alert throughout the city. In many ways, Havana plays like an attempt to create a Casablanca for a 1990 audience, complete with a mercenary, apolitical American hero with a romantic streak and a beautiful Swedish woman (Lena Olin) married to a charismatic revolutionary leader (played by an uncredited Raul Julia).
When he's killed and she's imprisoned, Jack uses blackmail and bribes to free her and run off together to America by New Year's Eve, but of course, it's never that easy (in case your Cuban history is rusty, that was the date that Batista was overthrown).
Havana is a throwback to the big studio pictures of the past. It recreates Havana as the Caribbean playground of the rich before the revolution in lavish detail, from the vintage cars and costumes to the magnificent casinos run by the American mob, and sets its romantic drama in the midst of the real-life revolution. Cuba under Batista is a corrupt dictatorship where the mob runs the casinos and the black markets with Batista's blessing, officials live on graft, American agents fill the cafes and casinos, and the oppressed peasants live in poverty—but don't mistake this for an apolitical film.
It's all a dramatic backdrop for a sweeping romantic thriller of beautiful people in an exotic but dangerous time and place. Director Sydney Pollack gives it a glossy, glamorous treatment with brief excursions to the seedy underbelly of Havana—even the battlefields outside the city are lushly photographed—and Redford brings movie star cool to his middle-aged player who seems surprised that it's no longer as thrilling.
Alan Arkin plays a savvy casino manager, Cuban actor turned spaghetti western icon Tomas Milian is a high-ranking Cuban official who sees the writing on the wall, and Mark Rydell plays New York mobster Meyer Lansky, who is struggling to keep his hold on the lucrative casino business.
The extravagant, beautifully-crafted romantic epic was a financial failure when it was released in 1990. While no forgotten masterpiece, it is still an entertaining piece of old-school Hollywood filmmaking: leisurely paced, handsomely presented, well-acted, and centered by a movie star performance. Kino Lorber's Blu-ray features commentary by film historian Sergio Mims.