Grace Kelly’s engagement ring in High Society 1956 wasn't a prop. It was her real life. Prince Rainier III had just proposed, and she wore that massive 10.47-carat Cartier emerald-cut diamond right on screen. It’s kinda wild when you think about it. This movie wasn't just a musical remake of The Philadelphia Story; it was a literal swan song for the soon-to-be Princess of Monaco.
People usually show up for the star power. You’ve got Bing Crosby, Frank Sinatra, and Grace Kelly. That’s a heavy-hitting trio. But honestly, the movie works because it doesn't take itself too seriously. It’s a Technicolor blur of jazz, champagne, and Newport Rhode Island yachts. It’s breezy.
The Musical DNA of High Society 1956
Most folks don't realize that High Society 1956 exists because of Cole Porter. He wrote the whole score specifically for this film. That’s a big deal. Usually, movie musicals of that era were just recycled Broadway hits. This was bespoke.
"True Love" became a massive hit. It’s the scene where Bing and Grace are on the boat. It’s soft. It’s sentimental. Crosby’s voice is like warm butter, and Kelly actually sings her own parts, which was a bit of a gamble back then. Most actresses were dubbed. She wasn’t a powerhouse vocalist, but her thin, delicate tone fits the character of Tracy Lord perfectly.
Then there’s "Well, Did You Evah!"
This song is basically the reason to watch the movie. It wasn't even supposed to be in there. Cole Porter pulled it from one of his older shows (DuBarry Was a Lady) because the producers realized they had Frank Sinatra and Bing Crosby in the same movie but didn't have a duet for them. Imagine that. You hire the two biggest crooners on the planet and forget to give them a song together. They recorded it in one day. The chemistry is obvious. They’re ad-libbing, poking fun at each other, and leaning into that "old guard vs. new guard" rivalry that defined their real-world careers.
Why the Newport Setting Changed Everything
The original play and the 1940 Katharine Hepburn movie were set in Main Line Philadelphia. Switching it to Newport for High Society 1956 was a masterstroke of production design.
Newport in the fifties was the peak of American "old money" aesthetics. The film used the actual Clarendon Court estate for some of the exteriors. It looks expensive because it was. The movie captured a specific moment in time—the transition from the stiff-upper-lip elegance of the 40s to the more relaxed, jazz-influenced cool of the 50s.
Louis Armstrong is there.
That’s the secret sauce. Satchmo plays himself, basically acting as a Greek chorus. His presence bridges the gap between the stuffy elite and the vibrant, changing world outside the mansion walls. When he kicks off the film with "High Society Calypso," he’s setting the stage. He tells the audience right away: Look, these people are rich and messy, but we’re gonna have a good time watching them.
Comparing the Lords: Hepburn vs. Kelly
You can't talk about High Society 1956 without the elephant in the room. Is it better than The Philadelphia Story?
Strictly speaking? No.
The 1940 version is a masterpiece of fast-talking screwball comedy. But they aren't trying to do the same thing. Katharine Hepburn played Tracy Lord like a bronze statue that needed to be cracked. Grace Kelly plays her like a woman who is tired of being a statue.
Kelly’s performance is actually a bit more vulnerable. She’s "the ice queen," sure, but you see the cracks earlier. When she gets drunk on champagne and starts dancing with Frank Sinatra’s character, Mike Connor, she’s genuinely funny. It’s a shame she retired right after this. She had a comedic timing that people often overlooked because she was so breathtakingly beautiful.
Frank Sinatra was also at a weird point in his career. He had just won his Oscar for From Here to Eternity and was the king of the world again. In High Society 1956, he plays the cynical reporter with a chip on his shoulder. He’s supposed to hate the rich, but he falls for Tracy anyway. His rendition of "You're Sensational" is Sinatra at his peak—smooth, effortless, and a little bit dangerous.
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The Fashion and the "Kelly Look"
Edith Head did the costumes. If you know anything about classic Hollywood, that name is everything.
The dresses in this movie defined the mid-fifties silhouette. The white swimming pool robe? Iconic. The floral organza gown she wears at the party? It’s been copied by designers for decades. Head knew how to dress Kelly to emphasize her "patrician" look while making her feel accessible.
It wasn't just about the clothes, though. It was about the lifestyle. The film sold a dream of endless summer nights, jazz festivals, and high-end heartbreak. It’s escapism in its purest form. Even the "poor" characters, like Sinatra and Celeste Holm, are dressed better than 90% of people today.
Behind the Scenes Chaos
It wasn't all smooth sailing.
The production was rushed to make sure it hit theaters before Grace Kelly’s wedding in April 1956. MGM wanted to capitalize on the "Wedding of the Century." They succeeded. The movie was one of the highest-grossing films of the year.
There was also the friction of egos. You had Crosby, who had been the top dog at the box office for twenty years, and Sinatra, who was the new "Chairman of the Board." Reports from the set suggest they were professional, but there was a definite sense of competition. Crosby was known for being a "one-take" guy. Sinatra liked to feel things out. Somehow, the director Charles Walters managed to balance those two massive personalities without the set exploding.
Acknowledging the Flaws
We have to be real: the plot is thin.
If you strip away the music, it’s a story about a woman who can’t decide which of three wealthy or successful men she wants to marry while her philandering father tries to give her life advice. It’s a bit dated. The "socialite" problems of 1956 feel light-years away from the reality of 2026.
Some critics at the time felt it was too glossy. They missed the biting wit of the original screenplay. And yeah, the pace slows down a bit in the second act when the musical numbers take over. But honestly? Who cares? You don’t watch High Society 1956 for a gritty social commentary. You watch it to see Louis Armstrong play the trumpet while Frank Sinatra pours a drink.
Practical Ways to Experience the Film Today
If you're going to watch it, don't just stream it on a phone. This is a movie that demands a big screen and good speakers. The Technicolor restoration on the Blu-ray is stunning. The blues of the Newport harbor and the reds of the party decor pop in a way that modern digital films rarely do.
- Check the Soundtrack: The original soundtrack album is a gem. Listen to the stereo mix of "Well, Did You Evah!" to hear the spatial separation between Sinatra and Crosby’s microphones.
- Watch for the Jewelry: Keep an eye on that Cartier ring. Knowing it’s her real engagement ring adds a layer of "meta" reality to her scenes with Crosby.
- Double Feature it: Watch The Philadelphia Story on a Friday night and High Society 1956 on a Saturday. It’s the best way to see how Hollywood’s "Golden Age" shifted its tone over sixteen years.
The movie ends with a wedding, but not the one you necessarily expect if you haven't seen the original. It’s a tidy wrap-up. It leaves you feeling like you’ve just spent a weekend at a party where you weren't cool enough to be invited, but someone let you slip in through the back door anyway.
To get the most out of your viewing, pay attention to the lyrics in "Mind If I Make Love To You." It’s one of the most underrated Sinatra ballads. It captures that exact moment of falling for someone you know you shouldn't. It's subtle, it's elegant, and it's exactly what this movie does best.
Check your local listings for any classic cinema screenings this summer. Seeing this in a theater with an audience is a completely different vibe than watching it solo. The laughs hit harder, and the music feels bigger. It’s a piece of history that still knows how to put on a show.