5 underrated Oscar-winning movies you should stream right now

We tend to overrate the value of winning an Academy Award. The more optimistic among Hollywood’s denizens believe it will confer upon their film a kind of immortality, but how many people today have seen John Ford’s How Green Was My Valley, which beat Citizen Kane for Best Picture in 1941, or 1967’s multi-Oscar-winning Doctor Dolittle, which features a love song to a seal?
The truth is, many great films have won Oscars and then faded into relative obscurity. While the films below may not be truly obscure, they offer a sample of the cinematic delights available to stream that are far from required viewing for most, despite their Academy wins.
The Wonderful Story of Henry Sugar (2023)
Wes Anderson won his first and so far only Oscar, for Best Live Action Short Film, for this 39-minute short based on the 1977 short story by Roald Dahl. Benedict Cumberbatch plays a gambler who trains himself on the teachings of an Indian guru to “see without using his eyes,” the better to multiply his winnings. It’s an utterly clean and straightforward little movie; the lack of miscellaneous decoration in the narrative ends up perfectly suiting Anderson’s more-is-more aesthetic. Overall, Henry Sugar is a lovely homage to the theater and staging tricks wrapped in appreciation for a literary master.
The Wonderful Story of Henry Sugar is streaming on Netflix.
A Room with a View (1985)

In 1985, the team at Merchant Ivory Productions – consisting of producer Ismail Merchant, director James Ivory, and screenwriter Ruth Prawer Jhabvala – had been making micro-budget literary adaptations for 20 years, many set in Merchant’s native India. Then they stumbled upon adapting the works of the British master E.M. Forster, resulting in three films that would win them some of their greatest acclaim. The first was A Room with a View, a Florence-set romance based on Forster’s early-career novel from 1908. It’s a gorgeous, lush film, painted in light, and starring the impossibly young Helena Bonham Carter in her first film role. It richly earned its three Oscars for Adapted Screenplay, Art Direction, and Costume Design.
A Room with a View is streaming on Max.
Stalag 17 (1953)
William Holden won Best Actor for this Billy Wilder film, about American airmen imprisoned in a German prisoner-of-war camp during World War II. Like all Wilder films, Stalag 17 is sharply written and frequently hilarious, playing on the camaraderie among the airmen as they stage an attempted escape (the film predates the more famous The Great Escape, covering similar circumstances, by a decade). Particularly delightful is the Austrian Jewish director Otto Preminger in a rare acting performance as the ruthless but ridiculous Nazi warden of the camp, Colonel von Scherbach. Preminger, himself a refugee from Nazi aggression, presumably reveled in the irony.
Stalag 17 is streaming on Tubi.
Gigi (1958)
Gigi, 1958’s Best Picture (among nine total Oscar wins of nine nominations), this movie musical based on a 1944 novella has a checkered reputation, and for good reason. The title character (Leslie Caron) is a young woman (the film declines to say exactly how young) being trained as a courtesan, or “kept woman,” in Belle Epoque Paris. She ultimately falls into the arms of a much older man (Louis Jourdan) – but as his intended, not as a mistress. Dated? Certainly. But what can’t be avoided is that Gigi is a feast for the senses, boasting possibly the most ravishing colors in any film musical and one of the best scores ever, by Alan Jay Lerner and Frederick Loewe, straight off their Broadway triumph with My Fair Lady. The title number, which won Best Original Song, is transporting – as another Lerner and Loewe song would have it, it’s almost like being in love.
Gigi is streaming on Tubi.
Blithe Spirit (1945)

Before he made The Bridge on the River Kwai, Lawrence of Arabia, and Doctor Zhivago, director David Lean co-wrote and directed this adaptation of the smash hit Noël Coward stage comedy from 1941. The all-time stage and screen heavy-hitter Rex Harrison plays a novelist who finds his house occupied both by his current wife (Constance Cummings) and deceased former wife (Kay Hammond) after a séance gone wrong. Effects artist Tom Howard, who would later help to handle SFX for 2001: A Space Odyssey, won the Best Visual Effects Oscar for his work on the film’s various ghosts, who luminesce an unearthly but alluring green.
Blithe Spirit is streaming on Max.