20 films that reunited beloved cinematic duos

Technically, “You’ve Got Mail” is the third movie pairing Tom Hanks and Meg Ryan. However, “Joe Versus the Volcano” was more of a cult film. “You’ve Got Mail” was viewed by many as a romcom re-pairing after 1993’s “Sleepless in Seattle.” That’s in part because both films were directed by Nora Ephron, so this felt almost like a spiritual sequel.

Who are one of the most iconic pairs of old Hollywood? Fred Astaire and Ginger Rogers, of course. The dancing duo (though Rogers was also a talented comedic and dramatic actor) made nine films together in the 1930s. They really used to churn out movies back in the Hollywood studio system. Then, a decade later, Rogers and Astaire reunited. “The Barkleys of Broadway” was actually kind of an accident. Judy Garland had to be replaced, so Rogers stepped in to act alongside Astaire one last time.

You likely remember “FernGully” (if you remember it at all) for Robin Williams’ riffing comedic turn. However, he was not the only comedian in the environmentally-inclined animated feature. There were also the tertiary characters Stump and Root, who were voiced by Cheech Marin and Tommy Chong. That one was for the adults in the audience, of course.

Animation can take a while, so perhaps what was a reunion in “Toy Story 4” wasn’t really intended to be a reunion. However, “Key & Peele,” the popular sketch comedy show, ended in 2015. Then, they voiced the characters Ducky and Bunny in “Toy Story 4.” Keegan-Michael Key is an actor and Jordan Peele mostly directs now, so we may never see the two in the same project again.

The ‘90s were big for “Hey, want to see Jack Lemmon and Walter Matthau together again?” movies. The original “Odd Couple” (on the big screen, at least) were both in “JFK,” but that doesn’t really count. “Grumpy Old Men” was fully built on reuniting Lemmon and Matthau as a comedic duo. In the ‘90s they also made “Grumpier Old Men” and “The Odd Couple II.”

Since the moment they won a screenwriting Oscar, Matt Damon and Ben Affleck have been synonymous with one another. It didn’t take long for a director to capitalize on the sensation that was “Good Will Hunting.” Affleck had worked alongside Kevin Smith previously, but for “Dogma,” Smith got Affleck and Damon to appear together. That was not the last time the two have reunited. 2026’s Netflix thriller “The Rip” is the most recent version of that.

Katharine Hepburn and Spencer Tracy are two of the most acclaimed actors in history. They also had a decades-long professional and personal relationship (Tracy never divorced his wife, leading to one of the most public affairs in history). After 1957’s “Desk Set,” it would be a decade until they reunited as a married couple in the race-focused drama “Guess Who’s Coming to Dinner.” Tracy’s declining health played a role in that, and indeed the actor died shortly after finishing the filming of “Guess Who’s Coming to Dinner.” Hepburn would wait until 1983, when Tracy’s wife died, before ever publicly acknowledging the romantic relationship.

“The Lake House” is a silly romantic drama about two people who fall for one another thanks to a magical mailbox that allows them to communicate through time, as they are staying at the titular lake house two years apart. The only juice the movie had is in the casting. Keanu Reeves and Sandra Bullock had popped together in “Speed,” and then Keanu (wisely) skipped the sequel. That meant “The Lake House” marked the first time Reeves and Bullock worked together since “Speed.”

Paul Newman and Robert Redford are thought of as an iconic movie duo. And yet, that is owed to exactly two movies. The first is “Butch Cassidy and the Sundance Kid,” a crowd-pleasing hit based on the movie-star charisma of Redford and Newman. A few years later, the two played criminals of a different sort, con men, in “The Sting.” The ‘70s were a strikingly different movie landscape, and to that end “The Sting” was a massive hit that also won Best Picture.

Speaking of massive hits that also won Best Picture, Leonardo DiCaprio and Kate Winslet will forever be tied together due to “Titanic.” As acclaimed actors, the two went off on their separate careers. Eventually, though, they would be repaired in “Revolutionary Road,” a bummer of a domestic drama. The whole thing screamed “Oscar bait,” but “Revolutionary Road” came and went like a blip on a radar screen, even with the re-pairing of Leo and Kate.

“The Wedding Singer” is one of the better Adam Sandler comedies, a period-piece romcom that paired Sandler with Drew Barrymore. Sandler and Barrymore would reunite a few years after that in “50 First Dates,” a romantic comedy that is, frankly, completely insane. There was a gap after that, but once Sandler's and Barrymore’s movie careers were waning to a degree, they joined forces in another Sandler vehicle, the romcom “Blended.”

The movie “Heat” is now considered a ‘90s classic, but at the time it was hyped because for the first time Robert De Niro and Al Pacino were going to share the screen together (bear in mind they are in different timelines in “The Godfather Part II.” They were both massive figures in film in 1995 when “Heat” arrived. By 2008, well, De Niro and Pacino were both collecting paychecks and losing cache. “Righteous Kill” tried to capture some of that “Heat” buzz by pairing De Niro and Pacino again, but the movie was so bad that the only people who have any connection to it these days are the members of Quaid Army.

Ben Stiller and Owen Wilson were both in “Meet the Parents,” but they weren’t really a comedic pairing in that film. That wouldn’t happen until “Zoolander,” a movie that weathered a rough release date (September 28, 2001) to become a cult classic. Riding that wave, Stiller and Wilson were paired again in the silly, spoofy take on the cop show “Starsky and Hutch,” a movie that is better than it has any right to be.

Tom Cruise and Nicole Kidman were one of the defining celebrity couples of the 1990s. Early on in the decade they made a couple films together — “Days of Thunder” and “Far and Away” — the latter of which heavily drafted off Cruise and Kidman as a couple. Then, the two signed on to make a movie about a fraying marriage directed by Stanley Kubrick. They would be divorced within a couple years of finishing “Eyes Wide Shut.” Good movie, though.

How do you get people to watch a romantic comedy in the 2020s, a timeframe wherein the genre, and comedy in general, struggles at the box office? You can try pairing up two movie stars who have found success before. George Clooney and Julia Roberts, of course, were in the “Ocean’s” movies together in the 2000s, a decade in which both were still big stars. By 2022 they, and the romcom, had faded, but Clooney and Roberts gave “Ticket to Paradise” a bit of juice.

Speaking of Roberts, she put a capper on her run as the queen of the ‘90s romcom with “Runaway Bride.” That tenure began, of course, with “Pretty Woman” in 1990. That movie co-starred Richard Gere. Gere returned to co-star with Roberts again in “Runaway Bride.” While the film is mediocre, “Runaway Bride” was a hit, in large part due to people wanting to see this duo together again.

Now, we go back to Clooney. Also, to the “Ocean’s” movie. “Wolfs” basically exists to have Clooney and Brad Pitt working together again. Having the two working together and bickering definitely evoked their dynamic in the “Ocean’s” trilogy. Plus, by 2024 Pitt was one of the last movie stars standing. And yet, “Wolfs” ended up an Apple TV exclusive and flew completely under the radar.

For a while, Will Ferrell was one of the biggest comedy stars, and movie stars, in the world. “Talladega Nights” was one of a few 2000s comedies in which Ferrell played a brash idiot, and was also one of a few sports comedies he made. In that movie, Ferrell and John C. Reilly showed chemistry playing idiots together. That led to “Step Brothers,” one of the biggest comedy hits of the new millennium. Once Ferrell’s star began to wane, though, he paired up with Reilly again for a comedic take on Sherlock Holmes. Alas, “Holmes & Watson” is a truly atrocious movie. It’s absolutely awful, and it also ended the comedy pairing of Ferrell and Reilly — and essentially put the final nail in the coffin of Ferrell’s run as a comedy star.

Going back to “Saturday Night Live” and particularly SNL's “Weekend Update,” Tina Fey and Amy Poehler have been paired together. While both had secondary roles in “Mean Girls,” their TV chemistry was first tapped into for a film in “Baby Mama.” Several years later, they did it again in “Sisters.” Now, neither movie is good, which is a good time to remember Fey is a limited actor and Poehler only really works in the sketch comedy and sitcom realm.

We’ll end with another classic “SNL” pairing. John Belushi and Dan Aykroyd were two members of the original “SNL” cast. They also starred together in the first “SNL” movie, the 1980 hit “The Blues Brothers.” The next year, Aykroyd and Belushi were paired again in the dark suburban comedy “Neighbors.” Unfortunately, and unexpectedly, “Neighbors” proved the end of the run for the duo. A couple months after the movie hit theaters, Belushi died of a drug overdose. “Neighbors” would be his last film.