High Society, directed by Charles Walters, opens with a hovering helicopter shot of the “cliff walk” in Newport, Rhode Island, lined with mansions built by the robber barons and tycoons of the unregulated Gilded Age. The film is a musical version of The Philadelphia Story, the George Cukor film adaptation of Philip Barry’s 1939 Broadway hit, which starred Katharine Hepburn, Cary Grant, and James Stewart. With Grace Kelly as heiress Tracy Lord, Bing Crosby as C.K. Dexter Haven (here a jazz composer), and Frank Sinatra as newspaperman Mike Connor, High Society transplants the action from Philadelphia to Newport, a symbolic apex of unbridled wealth. The film is peppered with mostly new songs by Cole Porter, the one exception being the Crosby-Sinatra duet of “Well Did You Evah?” (originally sung by Betty Grable in the 1939 Broadway musical “Du Barry Was a Lady”). There’s “True Love” (Crosby), “You’re Sensational” (Sinatra), “I Love You, Samantha” (Crosby), and “Who Wants to Be a Millionaire” (Sinatra and Celeste Holm). The intense neurotic screwball spirit of the original is diluted here, with the characters lost in palatial surroundings (a casualty of VistaVision, which prioritizes scenery, not faces). Tracy’s wedding to uptight George (John Lund) coincides with the Newport Jazz Festival, and so a subtext of the importance and “cool”-ness of jazz keeps making itself felt.

Since High Society is playing as the Rhode Island entry in TCM’s July series “50 States in 50 Movies,” I was interested to revisit it from my perspective as a not-born-but-raised Rhode Islander. Rhode Island is much more than Newport (and the Claus von Bülow murder trial). The southern portion of the state is beach towns and fishing ports. The Industrial Revolution flourished in Rhode Island, and we had annual grade-school field trips to Slater Mill, a historic textile mill in Pawtucket. Other field trips involved visits to the “Great Swamp,” a wooded area where a 1675 battle between the colonial militia and the Narragansett tribe resulted in an atrocious massacre (the anniversary commemorated every year by the Narragansetts); Gilbert Stuart’s birthplace (the painter whose famous “Lansdowne portrait” of George Washington was saved from the fires engulfing the capitol in the War of 1812 by the quick-thinking First Lady Dolley Madison); and finally, in a ghastly parade, Newport mansions (the most famous one being “The Breakers,” a 70-room summer “cottage” built by Cornelius Vanderbilt II). My senior prom was held in Rosecliff Mansion, another glittering gorgeous monstrosity. In High Society, both Tracy Lord and C.K. Dexter Haven live in mansions like this. They are the elite of the elite. 

One of the high spots in the film is the presence of Louis Armstrong and his band, including pianist Billy Kyle, bassist Arvell Shaw, and drummer Barrett Deems. Playing themselves, they are all friends of Dexter Haven, and provide accompaniment to the romantic shenanigans among Tracy, Dexter, Mike, and George. Louis Calhern (whose credits include Blonde Crazy, Duck Soup, Notorious, The Asphalt Jungle, and Blackboard Jungle) is a welcome presence as Uncle Willie (High Society would be his final film—he died that year). Cedric Gibbons’s art direction is quite literally breathtaking, with room after room unfurling, swoon-worthy color schemes, each space more exquisite than the last. There’s so much care given to every single detail and it’s a blessing and a curse. During heightened scenes, your eye keeps drifting around to check out the curtains and vases and wallpaper. 

The overriding problem is that High Society grapples in almost every moment with the insistent ghosts of the original. As much as you try to banish the image of Katharine Hepburn stalking through those rooms, eyes glimmering with haughty rebellion… she persists. The same goes for Grant and Stewart. The only actor in High Society who manages to make us forget the original performance is Celeste Holm, perfectly cast as the wise-cracking photographer from Spy magazine (played beautifully by Ruth Hussey in the original). Grace Kelly, in her final role before retiring from film to get married to a little-known fella named The Prince of Monaco, tries hard, but she’s miscast, and there’s only so much she can do. In the right material, she’s glorious, but she doesn’t have the willful streak of eccentricity so necessary to the role (written for Hepburn). There’s something touching in Kelly’s attempts, but she isn’t served by the almost total lack of close-ups. Kelly wore her actual engagement ring in the film, and it is so huge it could be seen from space.

Because this is 1956, some of the themes in the script pour almost inevitably into the conformism of the Eisenhower era, its squickiness about sex, its enshrining of virginity. All of these elements are present in the original, but somehow in 1940 they feel wilder, less controllable, not a validation of the generally accepted status quo. (The bit about Tracy’s personality being the cause of her father’s philandering is bad in both versions.) How would a true cultural oddball like Hepburn fare in the 1956 version of the story? She’d be thrown off the cliff walk! 

The Newport Jazz Festival had started just two years prior, and the lineup of artists is still awe-inspiring: Ella Fitzgerald, Oscar Peterson, Dizzy Gillespie, Billie Holiday, to name a few. The festival has existed in various permutations (and various locations) ever since. In 2004, the 50th anniversary of the festival, Ben Ratliff wrote in The New York Times: “The symbolic battle, all those years ago, was to make the world outside its own cabal take jazz seriously. This could more easily happen, it was decided, in a wealthy place that forced a certain kind of attention from social elites and the media. The jazz record producer and entrepreneur John Hammond, at a directors’ meeting for the festival in 1955, summed up the paradox. His mother was a Vanderbilt, and he didn’t share the family’s presentiments. ‘We have no particular love for Newport,’ he said. ‘Yet in one sense of the word we have brought democracy to Newport, which was the last place in the world where it could have been expected to be found in America.’”

High Society was made in 1956, when all of this was a very recent memory. Part of Newport’s resistance to having the festival there was racist in nature. They didn’t want an influx of African-Americans “invading” their enclave. It was a culture clash, and it was set up as a culture clash. A missed opportunity along these lines comes late in High Society. At the engagement party for Tracy and George, couples in tuxedos and gowns dance sedately. (Celeste Holm’s quip—“One of the prettiest sights in this pretty world is the sight of the privileged class enjoying its privileges”—has even more subversive bite here.) But when Dexter Haven and Louis Armstrong take the stage with “That’s Jazz,” they raise the roof.

Throughout the film, jazz is joked about or demeaned by other characters. The society snobs turn their noses up. Jazz is uncivilized (read: African-American). How could Dexter Haven, one of their own, reject his position in society to write jazz songs? And so “That’s Jazz” is his moment of triumph. Unfortunately, Walters keeps the camera solely on the performers, never cutting to the audience, thereby missing the chance to show the old-world crowd get swept away by the music. Bing Crosby so often played that kind of role, the hip dude strolling into a stuck-up world, showing people how to let loose. The 1950s keeps a stranglehold on him in High Society. And jazz is compartmentalized, isolated, deprived of its true cultural force. The “privileged class” won’t be having any of that, thank you very much.

Sheila O’Malley is a regular film critic for Rogerebert.com and other places including The Criterion Collection. Her blog is The Sheila Variations.