Entertainment TV & Film 7 Bing Crosby Classics A List of Great Movies Starring the Top-Grossing Star Share PINTEREST Email Print SIlver Screen Selection/Getty Images TV & Film Movies Classic Movies Best Movie Lists Comedies Science Fiction Movies War Movies International Movies Movies For Kids Horror Movies Movie Awards Animated Films TV Shows By Shawn Dwyer Updated November 26, 2017 Hollywood’s top box office star from 1944-48, Bing Crosby found stardom as a popular crooner, movie actor, radio and television star, and even entrepreneur. While mainly cast in musicals, Crosby shined in dramatic roles and won the Oscar in 1944 for his portrayal of the authority-bucking Father O’Malley. He also made seven incredibly successful Road to… comedies with Bob Hope and Dorothy Lamour, cementing his status as an iconic performer who found enormous success in multiple mediums. 01 of 07 East Side of Heaven - 1939 SIlver Screen Selection/Getty Images Made while on the cusp of super stardom, East Side of Heaven was a pleasant musical comedy that saw Crosby’s affable charm elevate standard material. Crosby played a singing cab New York City cabbie who finds himself reluctantly in possession of an abandoned baby. Along with his roommate (Mischa Auer), Crosby tries to find the baby’s parents while attracting some unwanted notoriety, until finally coming to a foregone conclusion inherent in the film’s premise. Co-starring Joan Blondell, East Side of Heaven was one of many simple, but irresistible comedies that increasingly endeared Crosby to an adoring public. 02 of 07 The Road to Morocco - 1942 Universal Studios The third of seven Road to… The Road to Morocco Road to… The Road to Morocco surprisingly earned an Academy Award nomination for Best Original Screenplay, and remains just as funny and fresh today as it did in 1942. 03 of 07 Going My Way - 1944 Donaldson Collection/Getty Images In his first year as Hollywood’s top box office draw, Crosby earned his career’s only Best Actor Academy Award for this feel good musical. Crosby showed off his dramatic chops as Father Chuck O’Malley, who bucks church authority in the form of the cranky Father Fitzgibbon (Barry Fitzgerald) by organizing the neighborhood’s street toughs into a choir. Fitzgibbon bristles at O’Malley’s more modern-minded attitude despite the fact that the younger pastor wants to save their church from financial ruin by using the choir to raise money. Perhaps a bit too sentimental for these dark and cynical times, Going My Way remains essential viewing for even the most casual classic movie fan. 04 of 07 The Bells of St. Mary - 1945 Republic Pictures Crosby reprised the happy-go-lucky Father O’Malley for Leo McCarey’s hugely successful sequel to Going My Way. This time O’Malley takes up the cause of St. Mary’s Academy, which like St. Dominic’s before it has fallen on hard times. O’Malley mildly battles the academy’s Sister Benedict (Ingrid Bergman) while helping to save a couple’s marriage, weakening the resolve of the academy’s mortgage holder, and staging a rousing rendition of the Nativity. Once again, Crosby was nominated for his performance but ultimately lost out to Ray Milland’s brilliant portrayal of a hopeless alcoholic in The Lost Weekend. Regardless, The Bells of St. Mary’s is good, clean fun, albeit a well-executed rehash of its predecessor. 05 of 07 The Country Girl - 1954 Paramount Pictures Taking a turn toward more dramatic roles, Crosby delivered an Oscar-worthy performance as a self-pitying drunk in this well-made melodrama from director George Seaton. Crosby played Frank Elgin, a once-famous Broadway star whose life and career slowly drowns inside a bottle. He gets the chance for a comeback when a young director (William Holden) tries to cast him as his leading man in a new play, only to blame his allegedly suicidal wife, Georgie (Grace Kelly), for holding him back. But a monstrous bender reveals that it’s Elgin who’s suicidal and his wife is the only thing preventing him from truly going over the edge. Crosby did receive a nomination for Best Actor, but it was Kelly who walked away with the Oscar for her star-making performance. 06 of 07 White Christmas - 1954 Image Copyright Amazon While thin on plot, White Christmas was one of Crosby’s highest-grossing films and one of the most fondly remembered Christmas-themed movies. Inspired by his hugely popular 1941 song of the same name, the Michael Curtiz-directed classic starred Crosby, Danny Kaye, Vera-Ellen, and Rosemary Clooney as four stars trying to put on a variety show in order to save an inn owned by an elderly general (Dean Jagger) that has fallen on financial hard times. Of course, there’s no real suspense here since the ending is a foregone conclusion, but the heart-warming tone helped make it a huge hit on the big screen and on television, even though Crosby had certainly showed that he could perform in more challenging material. 07 of 07 High Society - 1955 MGM Home Entertainment Returning to lighthearted musicals after his failed bid for another Oscar the previous year, Crosby joined Kelly and fellow crooner Frank Sinatra for this Technicolor remake of the classic screwball comedy, The Philadelphia Story (1940), which starred Katharine Hepburn, Cary Grant, and James Stewart. In this version, Kelly played a beautiful socialite about to marry a stuffed shirt (John Lund), only to find her nuptials interrupted by an amorous photographer (Sinatra) and her jazz musician ex-husband (Crosby). It’s Crosby’s character who turns the affair into a musical with renditions of “True Love,” “I Love You, Samantha,” and “Now You Has Jazz,” which he performed with Louis Armstrong and his band. While not held in the same regard as the original, High Society was a highly entertaining box office hit.