You know that feeling when you stumble onto a movie on a rainy Sunday and suddenly realize every single person on screen is a legend? That is the exact vibe of the cast of Chances Are. Released in 1989, this movie sits in that weird, wonderful pocket of the late eighties where high-concept reincarnation comedies were actually allowed to be heartfelt instead of just being one long joke. It’s got Cybill Shepherd, a very young Robert Downey Jr., Mary Stuart Masterson, and Ryan O'Neal. It’s basically a masterclass in chemistry that probably shouldn't have worked on paper.
The plot is kind of wild. Louie Jeffries dies, gets reincarnated as Alex Finch, and then—twenty years later—accidentally falls in love with his own daughter from his past life while trying to woo his former wife. Yeah. It sounds messy. But honestly, the actors make it feel sweet. It’s a testament to the era.
Robert Downey Jr. and the Energy of Alex Finch
Before he was Iron Man, Robert Downey Jr. was the king of the fast-talking, slightly frantic, charmingly disheveled leading man. In this film, he plays Alex Finch. Alex is a recent Yale graduate who starts getting these weird flashes of a life he never lived. Downey brings this frantic, nervous energy to the role that makes the supernatural element believable. You can see him twitching with the realization that he’s actually a middle-aged district attorney trapped in the body of a twenty-something kid.
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Watching him interact with Cybill Shepherd is where the movie really finds its legs. He has to balance being a "kid" with the soul of her dead husband. It’s a tightrope walk. If he plays it too old, it’s creepy. If he plays it too young, the romance doesn't feel real. He nails it. It’s the kind of performance that reminded people why he was considered the best actor of his generation long before the MCU existed.
Cybill Shepherd: The Heart of the Matter
Cybill Shepherd plays Corinne Jeffries, the widow who never really moved on. Honestly, Shepherd was at the peak of her Moonlighting fame around this time, and she brings that same sophisticated but slightly frazzled energy here. She’s the anchor. While everyone else is running around dealing with reincarnation vibes, she’s playing the grounded reality of grief.
The way she looks at Downey Jr. when she starts to realize something is "off" is incredible. It’s subtle work. Most people forget how good Shepherd was at playing the straight-faced romantic lead who could also handle a screwball comedy script. She had to sell the idea that she could be attracted to a guy young enough to be her son because she sees her late husband's soul in his eyes. Without her, the movie falls apart into a bad sitcom.
Ryan O'Neal and the "Best Friend" Trope
Then you’ve got Ryan O'Neal as Philip Train. Philip is the best friend who has been secretly in love with Corinne for two decades. O'Neal plays it with a sort of weary, handsome patience. It’s a bit of a thankless role—the guy who’s always there but never gets the girl—but O'Neal makes you actually root for him.
Philip is the one who has to witness the chaos. He’s the audience surrogate. When Alex Finch starts acting like Louie, Philip is the first one to get suspicious, and O'Neal plays that jealousy and confusion with a lot of nuance. It’s a far cry from his Love Story days, showing a more mature, slightly cynical side of his acting range.
Mary Stuart Masterson: The Complicated Daughter
We have to talk about Mary Stuart Masterson. She plays Miranda, Corinne’s daughter. This is where the movie gets "kinda" uncomfortable if you think about it too hard. Miranda falls for Alex, not knowing he’s basically her dad’s soul. Masterson was the "it" girl for these types of roles in the late eighties—think Some Kind of Wonderful.
She brings a genuine, modern-for-the-time spark to Miranda. She isn't just a love interest; she’s a smart, capable woman who is incredibly confused by this guy who seems to know everything about her family history. Her chemistry with Downey is electric, which makes the eventual reveal that they can't be together both hilarious and a little bit heartbreaking.
The Supporting Players and Director Emile Ardolino
Beyond the main four, the cast of Chances Are is rounded out by some great character actors. Henderson Forsythe is great as the "heavenly" registrar who messes up Alex’s reincarnation process. It’s a small role, but it sets the whole plot in motion.
Director Emile Ardolino deserves a lot of credit here. He’s the guy who directed Dirty Dancing, so he knew how to handle romance and rhythm. He treats the reincarnation not as a sci-fi trope, but as a catalyst for a family drama. He leans into the aesthetics of Washington D.C.—the rowing on the Potomac, the stately homes, the sense of history. It makes the "ghost" story feel more permanent.
Why the Chemistry Still Hits
Most modern rom-coms feel like they were assembled by an algorithm. They lack the "lived-in" feeling of this 1989 cast. When you watch Downey and O'Neal argue, it feels like two men who have a history, even though one of them is technically in a new body.
There's a specific scene where Alex (as Louie) starts reciting facts about their past life that only the inner circle would know. The way the cameras linger on the faces of the cast—the shock, the dawning realization—is a masterclass in ensemble acting. They aren't overacting. They are letting the weirdness of the situation sink in naturally.
Legacy of the Performances
Looking back, this film was a pivotal moment for several of its stars.
- Robert Downey Jr. proved he could carry a mainstream romantic lead role without losing his edgy indie cred.
- Cybill Shepherd solidified her status as a film actress outside of her television success.
- Mary Stuart Masterson continued her run as the definitive "cool girl" of the decade.
It’s also worth noting the soundtrack, featuring the hit "After All" by Cher and Peter Cetera. That song is inextricably linked to the performances. It captures that bittersweet feeling of a second chance that isn't quite what you expected.
Revisiting the Film Today
If you’re going to rewatch Chances Are, pay attention to the small stuff. Watch the way Ryan O'Neal handles the physical comedy of being frustrated by a younger man. Look at how Cybill Shepherd uses her eyes to show the conflict between her memory of her husband and the reality of the kid standing in front of her.
The movie manages to avoid being dated because the emotions are honest. Reincarnation is just the wrapper. The actual gift is a story about how we never really let go of the people we love, and how they sometimes show up in our lives in ways we don't recognize at first.
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Actionable Insights for Fans and Movie Buffs
To truly appreciate the cast of Chances Are, consider these steps:
- Compare and Contrast: Watch Robert Downey Jr. in this and then immediately watch him in Chaplin (1992). You can see the seeds of his physical comedy and mimicry being planted in the Alex Finch character.
- The Ardolino Connection: If you like the pacing of this film, check out Sister Act or Dirty Dancing. Emile Ardolino had a very specific way of making high-concept stories feel grounded and joyful.
- The Soundtrack Deep Dive: Listen to the lyrics of "After All" after watching the ending. The song actually spoils the movie’s emotional resolution, but it works because the performances sell the sentimentality so well.
- Look for the Nuance: Pay attention to the "Louie" habits Downey incorporates—like the way he holds a pen or his posture—which he subtly shifts as the movie progresses. It's a more technical performance than it gets credit for.