Stanley Donen was one of the most celebrated directors of Hollywood's Golden Age, particularly famous for his musicals. He started out as a dancer and choreographer before transitioning to directing in the late 1940s. Early hits included his collaborations with Gene Kelly, like On the Town, Singin' in the Rain, and It's Always Fair Weather. After significant box office success as a studio filmmaker, Donen went independent in the late '50s, producing further gems like Charade, Arabesque, and Bedazzled.

His style is visually striking, with impressive cinematography and intricate camerawork. At their best, Donen's movies marry technical dexterity with resonant themes and rich characterization. As a result, many of them are still held in high regard today. In particular, most of his films are larger-than-life in the best way. As Donen himself explains of his approach to filmmaking: "What we did was not geared towards realism but towards the unreal." These are Donen's finest movies.

10 'Indiscreet'

Released: 1958

"How dare he make love to me and not be a married man!" Anna Kalman (Ingrid Bergman) is a successful actress living in London who meets the charismatic diplomat Philip Adams (Cary Grant). Their initial encounter sparks a whirlwind romance, but complications arise when Philip reveals that he is already married. Despite their mutual attraction, Anna is hesitant to engage in an affair. However, they nevertheless find themselves entangled in a series of clandestine meetings and romantic escapades.

Indiscreet is an incredibly simple romantic comedy, with a straightforward plot and few surprises. Fortunately, the star power of the leads more than compensates for the slight material. It may not rise to the heights of their Alfred Hitchcock collaboration Notorious but it's still an enjoyable time. In particular, Grant and Bergman exchange a litany of fun and humorous dialogue. The movie is also worth checking out for its pioneering use of split-screen, which Donen deploys here for comedic effect.

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9 'Bedazzled'

Released: 1967

"Everything I've ever told you has been a lie. Including that." Before the 2000 remake starring Brendan Frasier, there was this retelling of the Faust legend with Dudley Moore in the lead role of Stanley Moon. He's a hapless man who sells his soul to the devil (Peter Cook) in exchange for seven wishes to win the heart of his beloved Margaret (Eleanor Bron). Cook steals the show as the suave and mischievous Satan, offering Stanley opportunities to fulfill his desires, but always with a clever twist.

Stanley asks for a number of boons, including being more articulate, being rich, and for Margaret to love him. However, these never worked out quite as he hoped. As Stanley's wishes take him on increasingly absurd and hilarious adventures, he learns valuable lessons about love, self-acceptance, and the true nature of happiness. It's a charming story jam-packed with barbed, witty dialogue that feels surprisingly fresh all these decades later.

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8 'Damn Yankees'

Released: 1958

"Whatever Lola wants, Lola gets; and little man, little Lola wants you!" In another riff on the story of Faust, this sports musical tells the story of Joe Boyd (Tab Hunter), a die-hard fan of the Washington Senators baseball team, who sells his soul to the devil, Applegate (Ray Walston), in exchange for the chance to become the young, talented baseball player and help the Senators defeat the dominating New York Yankees.

As "Joe Hardy", he leads the Senators to victory, but complications arise when he realizes the true cost of his deal with the devil, especially regarding his beloved wife, Meg (Shannon Bolin). Damn Yankees was first a Broadway musical with choreography by Bob Fosse, and Donen ably brought it to the screen (even though some of the hip movements in a few dances had to be axed, as the studios considered them too risqué for a movie.)

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7 'It's Always Fair Weather'

Released: 1955

"You don't have to hang around with me all evening. I wish I didn't have to hang around with myself." It's Always Fair Weather is a satirical musical that stands out with its more cynical tone. It follows three World War II buddies—Ted Riley (Gene Kelly), Doug Hallerton (Dan Dailley), and Angie Valentine (Michael Kidd)— who reunite ten years later to fulfill a promise they made on their last day together. However, they soon discover that they have drifted apart and are not the same friends they once were. Ted is now a jaded ad executive, Doug a womanizing boxing promoter, and Valentine runs a hamburger stand.

As they navigate their reunion in a changing world, they confront their past, present, and future while rediscovering the bonds of friendship. This is conveyed through vivid song and dance numbers, including iconic tunes like "Once Upon a Time" and "I Like Myself". The scene where the soldiers dance with trashcans on their feet is also iconic. Although not commercially successful, It's Always Fair Weather influenced many musicals that followed.

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6 'Funny Face'

Released: 1957

"Let's give 'em the old pizzazz!" Fred Astaire and Audrey Hepburn lead this musical rom-com as fashion photographer Dick Avery and the shy bookstore clerk turned reluctant fashion model Jo Stockton. Jo is swept into the glamorous world of high fashion and embarks on a whirlwind journey from Greenwich Village to Paris. Along the way, a spark develops between her and Dick, but obstacles threaten to keep them apart.

Astaire and Hepburn were two of the brightest stars of their era, and it's a treat to see them on-screen together, even if not every aspect of the movie has aged all that well. The film may have flopped at the box office, but there's no denying the caliber of the musical numbers. In particular, the closing song "'S Wonderful" has been covered endlessly. There's also a quirky, memorable scene where Jo does a kind of interpretative dance in a Parisian nightclub. Hepburn somehow turns this into a spellbinding moment.

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5 'On the Town'

Released: 1949

"I want you to know that my interest in you is purely scientific." Kelly and Donen's directorial debut is a bold musical centering on three sailors—Chip (Frank Sinatra), Gabey (Kelly), and Ozzie (Jules Munshin)—on an action-packed 24-hour shore leave as they explore the bustling streets of Manhattan in search of fun and romance. Along the way, they encounter a spirited cab driver named Hildy (Betty Garrett), an enchanting anthropologist named Claire (Ann Miller), and the vivacious nightclub singer Ivy (Vera-Ellen).

Their adventures unfold to a lively score by Leonard Bernstein, among others. The film crams a ton of fun and entertainment into its 98-minute runtime, including a neverending stream of energetic dances. As a result, On the Town was a big hit on release and is now regarded as a musical classic. It's also intriguing for the way it casts the famously suave Sinatra against type as an anxious, nerdy character. Plus, it has been praised for its complex, well-written female characters.

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4 'Seven Brides for Seven Brothers'

Released: 1954

"Pa used to say love is kind of like the measles. You only get it once. The older you are, the tougher it goes." Set in 1850s Oregon, Seven Brides for Seven Brothers focuses on Adam Pontipee (Howard Keel), a rugged backwoodsman, who marries Milly (Jane Powell) after a breakneck courtship. Upon bringing Milly home to his remote cabin, Adam reveals that he has six unruly brothers in need of wives. Determined to tame the rowdy bunch, Milly sets out to civilize the brothers and find them suitable brides.

However, when a harsh winter snows them in, the brothers resort to an unconventional method to find love: they kidnap six women and trigger an avalanche. An outraged Milly forces the men to sleep in the barn while the women stay in the house. Over time, though, some romance starts to blossom despite the bizarre situation. The film is certainly goofy, but that's also its charm. It is now frequently ranked among the greatest movie musicals of all time, with particular praise for its infectious songs.

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3 'Two for the Road'

Released: 1967

"At least you're not a bad-tempered, disorganized, conceited failure anymore. You're a bad-tempered, disorganized, conceited success." Perhaps Donen's most artistic and experimental project, Two for the Road is a portrait of a marriage on the rocks. It follows Mark (Albert Finney) and Joanna Wallace (Audrey Hepburn) as they take a road trip from England to the French Riviera. Their journey is interspersed with flashbacks of previous trips they have taken on the same route, which gradually reveal the complexities of their relationship.

The film received lukewarm reviews on release, but its critical standing has improved dramatically since, with many now ranking it as Donen's greatest film and Hepburn's most accomplished performance. It's confidently constructed, with every element in its right place; the work of a master craftsman with nothing left to prove. More than that, Two for the Road is emotionally intense and psychologically astute. For this reason, it has perhaps aged better than any of Donen's other films.

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2 'Charade'

Released: 1963

"She batted them pretty little eyes at you, and you fell for it like an egg from a tall chicken!" Charade is Donen's fusion of a thriller and a rom-com, starring Audrey Hepburn and Cary Grant as Regina Lambert and Peter Joshua. After her husband's mysterious death, Regina sets out on a quest to uncover the truth and the whereabouts of a fortune stolen during World War II. Peter helps her in her mission, but he is hiding secrets of his own.

As they make their way through a series of twists and turns, dodging sinister characters and uncovering hidden identities, Regina and Peter find themselves falling in love amidst the chaos. Charade makes for an impressive hybrid of romance and suspense, with its witty dialogue, white-knuckle tension, and stunning cinematography of Parisian landmarks. In fact, the thriller elements are handled so well that the film is frequently mistaken for a movie by Alfred Hitchcock. People thinking your movie was made by the Master of Suspense is certainly high praise.

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1 'Singin' in the Rain'

Released: 1952

"Come rain, come shine, come snow, come sleet, the show MUST go on!" When it comes to Donen's signature movie, it's hard to make a case for anything other than Singin' in the Rain, one of the most famous musicals ever made. Kelly plays Don Lockwood, a charismatic silent film star whose career faces upheaval with the advent of talking pictures. Alongside his friend Cosmo Brown (Donald O'Connor), and aspiring actress Kathy Selden (Debbie Reynolds), Don must make the transition to sound while grappling with love, fame, and artistic integrity.

Singin' in the Rain is old-fashioned entertainment done right, with a bevy of likable characters, puns and dad jokes, and killer choreography. The music is also legendary at this point, particularly the title song. Moreover, it's the kind of movie that simultaneously feels like a quintessential product of its era while also transcending it. Viewers will continue to enjoy its warmth and joy for decades to come.

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