The highly successful jazz musician C.K. Dexter Haven (Bing Crosby) was divorced from wealthy Newport, Rhode Island, socialite Tracy Samantha Lord (Grace Kelly), but remains in love with her. She, however, is about to get married to a bland gentleman of good standing, George Kittredge (John Lund).
Spy Magazine, a fictional tabloid newspaper in possession of embarrassing information about Tracy's father, sends reporter Mike Connor (Frank Sinatra) and photographer Liz Imbrie (Celeste Holm) to cover the nuptials. Tracy begins an elaborate charade as a private means of revenge, introducing her Uncle Willy (Louis Calhern) as her proper father Seth Lord (Sidney Blackmer) and the latter as her "wicked" Uncle Willy.
Connor falls in love with Tracy, who must choose among three very different men in a course of self-discovery. After becoming tipsy at a party on the eve of her wedding and going off with Connor for a romantic swim, Tracy decides to go through with it until Kittredge takes umbrage. While in the process of telling her guests that the wedding is off, Tracy is surprised by a proposal from Dexter to take the groom's place. Realizing where her heart truly is, she accepts.Bing Crosby as C. K. Dexter Haven
Grace Kelly as Tracy Samantha Lord
Frank Sinatra as Macaulay "Mike" Connor
Celeste Holm as Liz Imbrie
John Lund as George Kittredge
Louis Calhern as Uncle Willie
Sidney Blackmer as Seth Lord
Louis Armstrong and His Band as themselves
Edmond Hall – Clarinetist
Trummy Young – Trombonist
Billy Kyle – Pianist
Arvell Shaw – Bassist
Barrett Deems – Drummer
Margalo Gillmore as Mrs. Seth Lord
Lydia Reed as Caroline Lord
Gordon Richards as Dexter Haven's butler
Richard Garrick as Lords' butler
Filming took place between January and March 1956. The movie was shot mostly in and around Clarendon Court then owned by Claus von Bulow. The film stars Bing Crosby, Grace Kelly, Frank Sinatra, Celeste Holm, John Lund, Louis Calhern, Sidney Blackmer, Margalo Gillmore, and Lydia Reed, along with Louis Armstrong as himself. As name-checked by Crosby in the song "Now You Has Jazz", where each musician takes a small solo, Armstrong's band include: Edmond Hall (clarinet), Trummy Young (trombone), Billy Kyle (piano), Arvell Shaw (bass), and Barrett Deems (drums).
This film featured Kelly's final role before she became Princess of Monaco; it was released three months after her marriage to Prince Rainier III. In the movie Grace Kelly wore the Cartier engagement ring given to her by Rainier. Sinatra was 40 and Crosby 53 while playing the love interests of Kelly, who was only 26 during the filming. Sinatra biographers George Jacobs and William Stadiem make the claim that Crosby kept his distance from Sinatra during the production and remained strictly professional when Sinatra desired companionship, and that it "killed" Sinatra to think that Crosby considered himself a higher class singer. However this is refuted by TCM, which states that "in spite of a rumored rivalry between Frank Sinatra and Bing Crosby, the two worked together very amicably during the shoot."
They claim that Sinatra was fascinated with Grace Kelly – as were many of her previous co-stars – and would have loved to have an affair with her but feared rejection and embarrassment in front of Crosby, who had previously had an affair with Kelly.
Producer Sol C. Siegel paid Porter $250,000 for his first original film score in eight years; it introduced a couple of pop standards, including "True Love" and "You're Sensational". Not only did Sinatra and Crosby collaborate for the first time, but behind the scenes two master orchestrators – Conrad Salinger and Nelson Riddle – melded their arrangements under the baton of Johnny Green. Armstrong and his band get a couple of standout moments and Kelly has her only role in a musical.
- "High Society Calypso" – Armstrong & his band
- "Little One" – C.K.
- "Who Wants to Be a Millionaire?" – Mike, Liz
- "True Love" – C.K., Tracy
- "You're Sensational" – Mike
- "I Love You, Samantha" – C.K.
- "Now You Has Jazz" – C.K., Armstrong & his band, individually introduced by name
- "Well, Did You Evah!" – C.K., Mike
- "Mind if I Make Love to You?" – Mike
A soundtrack album was released the year of the film's release and was a major success in both America and the United Kingdom. It has been said that one of the main reasons star Sinatra was drawn to the film was a mock-tipsy duet with his boyhood idol Crosby on "Well, Did You Evah!", a song from an earlier Porter show, DuBarry Was a Lady (1939), re-adapted and added at the last minute when it was noted that the two singers did not have a duet to perform in the film.
The title of the song "Who Wants to Be a Millionaire?" gained new significance a half-century later as the title of a global game show franchise. "I Love You, Samantha" has also become a jazz favorite for improvisations.
Opening on July 17, 1956, High Society garnered mixed reviews, often being compared as a lesser offering to The Philadelphia Story, a previous adaptation in 1940 of the same play starring Cary Grant in the Crosby part, Katharine Hepburn in the Kelly role, and James Stewart in an Oscar-winning turn as the reporter played in the remake by Sinatra. Variety noted: "High Society should spell high finance business all over. It’s a solid entertainment every minute of its footage. Fortified with a strong Cole Porter score, film is a pleasant romp for cast toppers Bing Crosby, Grace Kelly and Frank Sinatra who, tactfully, get alphabetical top billing. Their impact is almost equally consistent. Although Sinatra has the top pop tune opportunities, the Groaner makes his specialties stand up and out on showmanship and delivery, and Miss Kelly impresses as the femme lead with pleasantly comedienne overtones. This is perhaps her most relaxed performance ..."
Bosley Crowther of The New York Times described it as "flimsy as a gossip-columnist's word," missing "the snap and the crackle that its un-musical predecessor had." According to Time, in spite of its "Who's Who cast" the film is "simply not top-drawer"; a "good deal of the screenplay seems as dated today as the idle rich ... [Kelly] lacks the gawky animal energy that Katharine Hepburn brought to the 1939 play and the 1941 movie, [Crosby] saunters through the part rather sleepily, without much of the old Bing zing[, and] Sinatra plays the reporter like a dead-end kid with a typewriter."
At the North American box office, High Society was a success. It was one of the 10 highest grossing films of 1956 in the US and Canada earning $5,602,000, and $2,656,000 elsewhere, resulting in a profit of $1,148,000.
High Society received two Oscar nominations, and nearly received a third in one of the more famous Academy Award gaffes. High Society initially was nominated in the 1956 Academy Awards for Best Motion Picture Story, even though the movie was based on the 1940 movie The Philadelphia Story and thus was not eligible in that category. Moreover, the nominated writers, Elwood Ullman and Edward Bernds, had written not this movie, but a 1955 Bowery Boys movie also called High Society.
According to the book Inside Oscar, Steve Broidy, president of The Bowery Boys home studio Allied Artists, told the press, "This just proves what we've known all along – that the Bowery Boys series couldn't have lasted this long if not for the fine writers." The joking in the press aside, Ullman and Bernds sent a telegram to the Academy Award Board of Governors, acknowledging the error and requesting that their names be removed from the final ballot.
More than 40 years following the film's release, it was adapted for the stage as a Broadway musical with several Porter songs from other sources added to the score. The Broadway production opened on April 27, 1998, at the St. James Theatre, where it ran for 144 performances.