The legendary Bing Crosby was born on May 3, 1903. Der Bingle was not only one of the most popular vocalists of all time, but he was a hit on the radio as well as being quite an accomplished actor, earning a Best Actor Oscar for his performance in 1944’s “Going My Way,” one of his three Oscar nominations. Crosby also earned a Golden Globe nom for 1951’s “Here Comes the Groom” and was named Best Actor for “The Country Girl” (1954) from the National Board of Review.
As an actor, Crosby proved himself to be extremely versatile, from starring in musicals (of course), but also dramas, romantic comedies and even a Western (1966’s “Stagecoach”). For 15 years, he was the among the Top 10 acts in box office, and from 1944-1948, Crosby was actually number one. During the course of his recording career, Crosby charted 396 singles and had 25 songs that reached number one. After winning the Oscar for his performance as Rev. Chuck O’Malley in “Going My Way,” Crosby returned as O’Malley in 1945’s “The Bells of St. Mary’s” and earned an Oscar nomination again, becoming the first of six actors in history who received two different Oscar nominations for playing the same character.
So let’s raise a glass to the great Bing Crosby, ranking his 12 best screen performances. Our photo gallery above includes the titles already mentioned, plus “Holiday Inn,” the “Road” movies with Bob Hope and more.
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12. ROBIN AND THE 7 HOODS (1964)
Image Credit: Warner Bros/Kobal/Shutterstock Director: Gordon Douglas. Writer: David R. Schwartz. Starring Frank Sinatra, Dean Martin, Sammy Davis Jr., Bing Crosby, Peter Falk.
Although not considered a great film, this gangster-set adaptation of “Robin Hood” is kind of a hoot. Here the famous Rat Pack of Frank Sinatra, Dean Martin and Sammy Davis Jr. donned flashy suits and fedoras to retell the legend of Robin Hood in 1930s Chicago. Crosby comes on board as Alan A. Dale, who, in the Robin Hood legend is a wandering minstrel who joins his band of merry men, but here runs an orphanage to which the mobsters make a significant donation, thus creating the myth that members of Sinatra’s gang are Robin Hoods in disguise. There are no deep performances here — “Robin and the 7 Hoods” is meant as a romp, and Crosby looks as if he’s having a great time.
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11. STAGECOACH (1966)
Image Credit: Moviestore/Shutterstock Director: Gordon Douglas. Writer: Joseph Landon. Starring Ann-Margret, Bing Crosby, Alex Cord, Red Buttons, Mike Connors, Van Heflin.
Crosby took a rare Western role in this remake of the famed 1939 John Ford film that made John Wayne a star. Although renamed as Josiah Boone, he takes on the role of an alcoholic doctor that brought Thomas Mitchell an Oscar in the original. Crosby’s take on the character is slightly different than Mitchell’s, as he brings a certain celebrity gravitas to the role and takes the spotlight whenever he speaks. His performance in “Stagecoach” suggests that Crosby, whose career had always been as a leading man, might have achieved a significantly important new facet in his career as a character actor should he have chosen to follow that route.
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10. THE EMPEROR WALTZ (1948)
Image Credit: Bud Fraker/Paramount/Kobal/Shutterstock Director: Billy Wilder. Writers: Billy Wilder, Charles Brackett. Starring Bing Crosby, Joan Fontaine, Richard Haydn.
“The Emperor Waltz” is one of the oddest films in the careers of both Crosby and co-writer/director Billy Wilder. Set in turn-of-the-century Vienna, the film features Crosby as gramophone salesman Virgil Smith who, anxious to popularize the machine in Austria, sets out to convince the country’s popular emperor Franz Joseph (Richard Haydn) to purchase one. Complications ensue when Virgil falls in love with a beautiful countess (Joan Fontaine) whose prized poodle Scheherezade suffers a nervous breakdown. (I kid you not.) Although incredibly the story is based on a real-life incident, the preposterousness of the plot is salvaged by Wilder and his co-writer Brackett with their skillful script and the believable performance by Crosby.
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9. ANYTHING GOES (1936, 1956)
Image Credit: Moviestore/Shutterstock Directors: Various. Writers: Various, based on the musical by Guy Bolton, P.G. Wodehouse. Starring Bing Crosby.
Crosby had the rare opportunity in the 1956 remake of the Cole Porter musical classic to play the same role as he did in the 1936 original film adaptation. In the first version, Crosby played Billy Crocker, a young Wall Street broker who is attracted to heiress Hope Harcourt, who is about to board a ship headed to London, along with Billy’s friend, chanteuse Reno Sweeney. In the 1956 film, Billy is renamed Bill Benson, an entertainer who boards the ship in search of a dancer for his new show, and, finding a great dancer, signs her, unaware that his partner Ted has signed another dancer for the same role. Crosby brings a youthful vitality to Billy in the 1936 version and a world-weary wisdom to Bill in the later incarnation.
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8. WHITE CHRISTMAS (1954)
Image Credit: Moviestore/Shutterstock Director: Michael Curtiz. Writers: Norman Krasna, Norman Panama, Melvin Frank.
Starring Bing Crosby, Rosemary Clooney, Danny Kaye, Vera-Ellen. Despite the title of the film, the classic Crosby holiday song was not introduced in this musical which focuses on two GIs, Bob Wallace (Crosby) and Phil Davis (Danny Kaye), who team up to form a musical act that quickly becomes popular in nightclubs and on the radio. The guys fall for two sisters — Betty (Rosemary Clooney) and Judy Haynes (Vera-Ellen) — and accompany the women on a trip to a mountain retreat in Vermont that just happens to be owned by a GI colleague. The inn is in trouble because there’s very little snow, so the four perform there to help pay expenses, and wouldn’t you know it? It begins to snow. “White Christmas” is a great example of Crosby in his element.
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7. HIGH SOCIETY (1956)
Image Credit: MGM/Kobal/REX/Shutterstock Director: Charles Walters. Writer: John Patrick, based on Philip Barry’s Play “The Philadelphia Story.” Starring Bing Crosby, Grace Kelly, Frank Sinatra, Louis Armstrong.
Philip Barry’s romantic comedy “The Philadelphia Story,” which was made into an acclaimed film in 1940, would seem to be an ideal basis for a musical. With music by Cole Porter and a cast that includes Crosby, Grace Kelly and Frank Sinatra (Oscar winners all), the film clearly comes with a top-flight pedigree. If the final product doesn’t quite live up to its pedigree, it nonetheless has its moments with solid Porter songs and a sense of easy-going fun by its cast.
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6. HERE COMES THE GROOM (1951)
Image Credit: Shutterstock Director: Frank Capra. Writers: Virginia Van Upp, Liam O’Brien, Myles Connolly. Starring Bing Crosby, Jane Wyman, Alexis Smith, Franchot Tone, James Barton.
Crosby earned his sole Golden Globe nomination for his performance as Pete Garvey, a newspaper reporter stationed in Paris, who only has a few days to get back with his former fiancée Emmadel Jones (Jane Wyman) or else he will lose custody of the orphans whom he has adopted. Unfortunately, Emmadel is currently engaged to another man, aristocrat Wilbur Stanley (Franchot Tone) and getting back with Pete is out of the question. For now. Although the plot suggests that “Here Comes the Groom” is a thoroughly disposable comedy, Crosby is very good in it, and his Globe nomination as not unwarranted.
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5. HOLIDAY INN (1942)
Image Credit: Moviestore Collection/REX/Shutterstock Director: Mark Sandrich. Writer: Claude Binyon, from a story by Irving Berlin. Starring Bing Crosby, Fred Astaire, Marjorie Reynolds, Virginia Dare.
This is the film in which Crosby introduced his biggest hit song, “White Christmas,” one of twelve new songs that Irving Berlin wrote for the film. Jim (Crosby), Ted (Fred Astaire) and Lila (Virginia Dare) make up a popular New York musical trio, but while Jim is strongly attracted to Lila, she has deep feelings for Ted and runs away with him, thus breaking up the trio. A year later, Jim plans to turn his farm into a music club that will only be open on holidays and meets singer Linda (Marjorie Reynolds) who signs on to appear at Holiday Inn. With solid direction from Mark Sandrich and those wonderful Berlin songs, “Holiday Inn” is one of Crosby’s strongest romantic comedies.
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4. THE ROAD series (1940, 1941, 1942, 1946, 1947, 1952, 1962)
Image Credit: Austral/Shutterstock Directors: Various. Writers: Various. Starring Bing Crosby, Bob Hope, Dorothy Lamour.
Crosby’s greatest popular film successes were undoubtedly the seven “Road To…” comedies that he made with his pal Bob Hope. The two had such a natural chemistry together that audiences couldn’t get enough of them, starting with “Road to Singapore” (1940) and continuing with “Road to Zanzibar” (1941), “Road to Morocco” (1942), “Road to Utopia” (1946), “Road to Rio” (1947), “Road to Bali” (1952) and winding up with “Road to Hong Kong” (1962). In all but “Hong Kong” they were joined by Dorothy Lamour, who spoofed her own “sarong” films of the 1930s, with Crosby playing the straight man to Hope, who was one of the first film actors to break the fourth wall, often commenting directly to the audience about the quality (or lack thereof) of the film they’re currently watching.
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3. THE BELLS OF ST. MARY’S (1945)
Image Credit: RKO/Kobal/REX/Shutterstock Director: Leo McCarey. Writer: Dudley Nichols. Starring Bing Crosby, Ingrid Bergman, Henry Travers, William Gargan.
A year after his performance as Rev. Chuck O’Malley won him the Best Actor Oscar, Crosby donned the collar once again as O’Malley and earned yet another Oscar nomination. Here Father O’Malley is reassigned to help the rapidly aging St. Mary’s School. While his solutions are practical, Sister Mary Benedict (Ingrid Bergman) takes a more spiritual approach, content that God will provide for them. This will not be the first time that the practical priest and the headstrong nun butt heads in the film, and Crosby and Bergman are absolutely terrific together.
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2. THE COUNTRY GIRL (1954)
Image Credit: Paramount/Kobal/REX/Shutterstock Writer/Director: George Seaton, based on the play by Clifford Odets. Starring Bing Crosby, Grace Kelly, William Holden.
Crosby took a huge chance by taking on the role of Frank Elgin, a fading actor who, thanks to his insecurities, has become a suicidal alcoholic. Frank’s condition has placed enormous stress on his wife Georgie (Grace Kelly in her Oscar-winning role), but things may be looking up for him when director Bernie Dodd (William Holden) casts him in his upcoming new musical. Bernie initially blames Georgie as the cause of Frank’s many problems, a ruse to disguise the fact that Bernie is secretly in love with her. For his performance as Frank, Crosby earned his third Oscar nomination and won the National Board of Review award as the year’s best actor.
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1. GOING MY WAY (2016)
Image Credit: SNAP/REX/Shutterstock Director: Leo McCarey. Writers: Frank Butler, Frank Cavett. Starring Bing Crosby, Barry Fitzgerald, Risë Stevens.
Crosby’s most beloved performance is likely his first film as Father Chuck O’Malley in Leo McCarey’s “Going My Way.” O’Malley is a young priest who is assigned to take over the affairs of New York’s St. Dominic’s Church, a duty kept secret from the parish’s pastor, Father Fitzgibbon (Barry Fitzgerald, in his Oscar-winning performance), who takes an immediate dislike to the young priest’s casual style. It becomes a fine line that Father Chuck has to walk to be able to do his job while winning over the cantankerous older priest. For his performance as Father O’Malley, Crosby won his first Academy Award.
