High Society is a 1956 American musical comedy film directed by Charles Walters and starring Bing Crosby, Grace Kelly, and Frank Sinatra. The film was produced by Sol C. Siegel for Metro-Goldwyn-Mayer, and shot in VistaVision and Technicolor, with music and lyrics by Cole Porter. Based on the play The Philadelphia Story by Philip Barry, with a screenplay by John Patrick, the film is about a successful popular jazz musician who tries to win back the affections of his ex-wife, who is preparing to marry another man. The jazz musician encounters additional competition from an undercover tabloid reporter, who is also in love with his ex-wife, who now must choose among three very different men. High Society was the last film appearance of Grace Kelly, before she became Princess consort of Monaco.

Bing Crosby as C.K. Dexter-Haven
Grace Kelly as Tracy Samantha Lord
Frank Sinatra as Macauley "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  

 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 father Seth Lord (Sidney Blackmer) and the latter as her Uncle Willy.

 Connor falls in love with Tracy, who must choose among three very different men in a course of self-discovery.

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 had an affair with her but feared rejection and embarrassment in front of Crosby

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 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: "Fortified with a strong Cole Porter score, film is a pleasant romp for cast toppers Bing Crosby, Grace Kelly and Frank Sinatra. Their impact is almost equally consistent. Although Sinatra has the top pop tune opportunities, the crooner makes his specialties stand up and out on showmanship and delivery, and Kelly impresses as a femme lead

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 .

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