The It's Always Fair Weather Movie Cast: Why This Cynical Masterpiece Nearly Broke Its Stars

The It's Always Fair Weather Movie Cast: Why This Cynical Masterpiece Nearly Broke Its Stars

Ten years after the war, three buddies meet at a bar. They realize they hate each other. That’s the premise. Honestly, it’s a bit of a bummer for a 1950s Technicolor musical, right? But that’s exactly why the it's always fair weather movie cast is so fascinating to look back on today. This wasn't your typical "Singin' in the Rain" fluff. It was sharp. It was bitter. It was basically the "Seinfeld" of MGM musicals before anyone knew what that meant.

Gene Kelly was at the center of it all, playing Ted Riley. By 1955, the Golden Age of Hollywood musicals was starting to feel the squeeze from television. You can see that tension on screen. Kelly isn't just dancing; he’s performing with a chip on his shoulder. It’s brilliant. Alongside him, you’ve got Dan Dailey as Doug Hallerton and Michael Kidd as Angie Valentine. If you’re looking for a group of men who can radiate "we’ve made terrible life choices," this is the trio.

The Trio That Redefined the Screen Musical

Gene Kelly was already a god at MGM. He’d done An American in Paris. He’d changed the world with Singin' in the Rain. But by the time the it's always fair weather movie cast came together, things were getting complicated. Kelly wanted to push boundaries. He didn't want a love story; he wanted a story about the passage of time and the rot of disappointment.

Dan Dailey was a massive get for the film. He was on loan from 20th Century Fox, and he brought this frantic, booze-soaked energy to the role of Doug, the guy who sold out to become a high-strung advertising executive. Dailey’s "Situation-Wise" number is a masterpiece of controlled chaos. It’s a literal nervous breakdown set to music. You don't see that often in the classics.

Then there’s Michael Kidd. Most people know him as the genius choreographer behind Seven Brides for Seven Brothers. This was actually his big acting debut. He plays the "normal" one who stayed in their hometown to run a burger joint. Kidd wasn't a singer, and he’ll tell you he wasn't really an actor, but his athleticism keeps up with Kelly and Dailey in ways few others could. Watching the three of them dance with garbage can lids on their feet—a sequence called "The Binge"—is a reminder of the raw physical labor these guys put into their craft.

Cyd Charisse and the Battle Against the Small Screen

You can't talk about this film without mentioning Cyd Charisse. She plays Jackie Leighton, a high-powered, hyper-intelligent TV executive. Charisse was arguably the greatest dancer in Hollywood history, but here, she has to be the smartest person in the room too.

💡 You might also like: Not the Nine O'Clock News: Why the Satirical Giant Still Matters

Her big number, "Baby You Knock Me Out," takes place in a boxing gym. It’s weird. It’s sweaty. It’s incredibly cool. She’s surrounded by punch-drunk boxers while she rattles off statistics and delivers flawless jazz choreography. Charisse often mentioned in later interviews that working with Kelly was demanding. He was a perfectionist. He didn't just want you to be good; he wanted you to be an extension of his vision.

The film also serves as a massive satire of 1950s television. Dolores Gray plays Madeline Bradville, the host of a sappy, "This Is Your Life" style show. She is hilarious. She’s the personification of everything the it's always fair weather movie cast was trying to critique: the phoniness of modern media. Her song "Thanks a Lot, but No Thanks" involves her blowing up various suitors with explosives. It’s dark stuff for 1955.

Behind the Scenes Drama: A Cast at Odds

The vibe on set wasn't always "fair weather."

Gene Kelly and Stanley Donen had co-directed On the Town and Singin' in the Rain. They were a powerhouse duo. But by this film, their relationship had completely soured. Donen didn't even want to do the movie. He felt like he was being forced into it by Kelly.

  • The CinemaScope Struggle: This was Kelly’s first time working with the wide CinemaScope lens. He hated it. He felt the wide frame was "terrible for dancing" because it left too much dead space on the sides.
  • The Solos: Because the directors weren't getting along, the movie feels fragmented. Each of the three leads has a major solo that explains their character’s misery.
  • The Cut Content: Michael Kidd actually had a solo number that was cut from the final film, which reportedly didn't help the backstage mood.

Basically, the friction you see between the characters? It wasn't all acting. Donen later said he only did the film out of a sense of obligation, and he and Kelly didn't work together again for decades. That tension is palpable. It gives the movie a jagged edge that separates it from the sugary musicals of the 1940s.

📖 Related: New Movies in Theatre: What Most People Get Wrong About This Month's Picks

Why the Performers Matter More Than the Plot

The plot is simple: three GIs swear to meet at "Max the Butcher’s" bar exactly ten years after V-J Day. When they do, they realize they have absolutely nothing in common.

One is a cynical gambler (Kelly), one is a miserable corporate hack (Dailey), and one is a simple family man (Kidd). The brilliance of the it's always fair weather movie cast is how they handle the "inner monologue" sequences. Using a technique that was pretty revolutionary for the time, the film uses voiceovers so we can hear what the characters are thinking while they smile at each other across the table. They’re all thinking the same thing: Who are these losers?

It’s relatable. Who hasn't gone to a high school reunion and felt that immediate disconnect?

The Musical Numbers You Need to Re-watch

If you’re revisiting this, don't just look at the hits. Look at the weird stuff.

  1. "I Like Myself": Gene Kelly dancing on roller skates. This is the peak of his career. He did it because he wanted to prove he could still do something "impossible." No stunt doubles. Just Kelly, skates, and a busy New York City street.
  2. "The Binge": The garbage can lid dance. It’s loud, rhythmic, and physically exhausting.
  3. "Situation-Wise": Dan Dailey’s takedown of corporate culture. It’s frantic and genuinely funny.

The Legacy of a "Failed" Classic

When the movie came out, it didn't do great. People wanted the happy Gene Kelly. They didn't want the guy who was mad at the world. But over time, the it's always fair weather movie cast has been vindicated by critics and film historians. It’s now seen as the "final" great MGM musical.

👉 See also: A Simple Favor Blake Lively: Why Emily Nelson Is Still the Ultimate Screen Mystery

It was the end of an era. Shortly after this, the big studio system began to crumble. Audiences were staying home to watch TV, the very thing this movie mocked.

Looking at the cast now, you’re seeing the last stand of the triple-threat performer. These weren't just actors; they were athletes and musicians. They spent weeks rehearsing a single four-minute sequence. Michael Kidd brought a choreographer's precision to his acting, Dan Dailey brought a vaudevillian's timing, and Gene Kelly brought the sheer force of his will.


How to Appreciate This Movie Today

To truly get the most out of the it's always fair weather movie cast, you have to look past the bright colors.

  • Watch the eyes. In the opening bar scene, watch how Kelly, Dailey, and Kidd look at each other. The disappointment is real.
  • Notice the choreography of the crowds. Stanley Donen and Gene Kelly were masters at using the entire frame, even if they hated the wide screen.
  • Contrast it with Singin' in the Rain. If that movie is about the joy of creation, this one is about the reality of aging.

If you're a fan of the genre, your next step is to find the "Making Of" documentaries usually included on the Blu-ray releases. They detail the exact moments where Kelly and Donen’s friendship ended. It’s a fascinating look at how great art can come from genuine conflict. Also, keep an eye out for the deleted scenes—specifically Michael Kidd’s lost footage—which provide even more context for his character's arc.

This isn't a movie that leaves you humming a happy tune. It’s a movie that makes you think about your own old friends and the person you used to be. That’s why it’s a masterpiece.