Together again: 18 movies that reunited popular costars

While both Matt Damon and Ben Affleck had been acting for a while, they broke through together with “Good Will Hunting,” which they not only co-starred in, but won an Oscar for writing. Before he became a movie star, though, Kevin Smith had given Affleck some roles, and Damon joined Affleck in doing a solid by the director. The two co-starred as fallen angels in “Dogma.” Also, they played themselves and their “Good Will Hunting” characters in “Jay and Silent Bob Strike Back.”

The first time Tom Hanks and Meg Ryan paired up in a romantic comedy? That would be “Joe Versus the Volcano,” a fun, quirky movie that was not a big hit. Instead, it was “Sleepless in Seattle” that made them pop as a rom-com couple. Six years after that film, they would be reunited in the AOL-centric rom-com “You’ve Got Mail.” Now, both movies were directed by Nora Ephron, but Hanks and Ryan were not regulars in her films, so this counts as a proper reunion.

“Bogie and Bacall.” When you are a twosome that has your names joined together like that, you certainly belong on a list like this. Humphrey Bogart and Lauren Bacall were married from 1945 until Bogart’s death in 1957 (he was a bit older than Bacall and also not the most health-conscious), and they also starred together in four movies. The two actually met while filming 1944’s noir classic “To Have and Have Not,” which was Bacall’s debut movie. Once they were a couple, though, they could be promoted as a duo in “The Big Sleep,” another noir classic.

“Pulp Fiction” was a cultural phenomenon, so much so that John Travolta and Samuel L. Jackson became joined together thanks to their turns as two fast-talking hitmen. It’s a bit surprising that it took until 2003 for Travolta and Jackson to be reunited. It didn’t work, though. “Basic” is a mess of a movie, and it didn’t even make back its budget. The failure of “Basic” played a role in it being the last film, to date, by director John McTiernan. The other reason is that um, he went to prison for lying to the FBI and perjury in a wiretapping scandal.

Spencer Tracy and Katharine Hepburn are two of the most acclaimed actors of all time. They had an open affair that lasted over two decades (Tracy dipped out on his wife for good but the two never divorced). While Hepburn and Tracy made nine movies together, only a few of them really pop and feel like “Hepburn and Tracy together again!” movies. One of those is certainly “Adam’s Rib,” which feels like the quintessential “Hepburn and Tracy” film. The two play married lawyers who end up on opposite sides of a trial.

“Out to Sea” is probably the foremost movie built on a reunion of Jack Lemmon and Walter Matthau because, c’mon, why else would anybody see “Out to Sea?” However, it is not the first significant reuniting of these costars, and certainly not the best. “The Fortune Cookie” saw the duo together for the first time, a movie for which Matthau won an Oscar. When Neil Simon’s play “The Odd Couple” was adapted for the big screen, Lemmon and Matthau were selected to play Felix and Oscar, respectively. The movie poster literally says, “Jack Lemmon and Walter Matthau are The Odd Couple…say no more.”

Man, they really churned out movies back in the day. Fred Astaire and Ginger Rogers starred in 11 movies for RKO, and they made all of them between 1933 and 1939. A decade after their last movie for RKO, MGM had an idea. Astaire and Rogers were reunited after 10 years apart for “The Barkleys of Broadway.” Obviously, the full selling point of that one was the chance to see the dancing duo together again.

“Tommy Boy” made both Chris Farley and David Spade movie stars. Both of them were making their debuts as movie stars, and they won the MTV Movie Award for Best On-Screen Duo. Hollywood didn’t wait to try and strike gold again. The very next year, “Black Sheep” was released and reunited Farley and Spade. It was not as good, and not as successful, and the two never got to make a movie together again (in part due to Farley’s untimely death, one imagines).

Paul Newman and Robert Redford took their movie stardom to a new level with “Butch Cassidy and the Sundance Kid.” It was a huge hit and a critical darling. A few years later, Newman and Redford played criminal partners again in “The Sting.” This time, they were even more successful. Not only was it the second-highest-grossing movie of the year, but “The Sting” won Best Picture. And yet, the two actors never really had a major pairing again.

“Swingers” is a true cult hit, and a massive indie success. Doug Liman’s directorial career effectively began, and Jon Favreau successfully wrote himself a starring role that helped him bolster his acting career. Of course, the breakout star was the actor who played Favreau’s Mike’s smooth-talking friend Trent, one Vince Vaughn. Several years later, with the cult of “Swingers” established, the two reunited for “Made.” Maybe the “Swingers” fandom wasn’t sizable enough, though, as “Made” wasn’t a huge hit. It is significant, though, because Favreau made his directorial debut, paving the way for movies like “Elf” and “Iron Man.”

“Romancing the Stone” is both an adventure film and a romantic comedy. That’s tough to pull off, but the chemistry of Michael Douglas and Kathleen Turner helped make it work. The success of the movie was important to film history, as it essentially saved Robert Zemeckis’ directing career and allowed him to finally make his dream project, a little film called “Back to the Future.” There was a sequel, “The Jewel of the Nile,” but that obviously doesn’t count. You know who else was in these two movies, though? Danny DeVito, and for his black comedy “The War of the Roses,” a film about a vicious marital battle, he cast Douglas and Turner as the couple.

“Pretty Woman” was a huge hit, it has a bananas premise that would likely never be tried today, and it likely only worked thanks to the work of Richard Gere and a young, up-and-coming actress named Julia Robert. Years later, Garry Marshall needed an actress who could make a woman who becomes famous (somehow) for constantly leaving men at the altar likable. He went with Roberts, and he brought Gere back to play the reporter tasked with writing a story about her.

“Bridesmaids” was an ensemble cast, but Melissa McCarthy really popped, even getting an Oscar nomination for an outright comedy. Kristen Wiig was also in the huge hit as the ostensible lead. The two would take semi-lead roles in another comedy that is a bit of an ensemble piece. That would be the “Ghostbusters” movie that became needlessly part of the hot-take churn on the internet. All that for a perfectly fine, kinda funny reboot of a classic comedy.

“Silver Streak” was not designed as a pairing of Richard Pryor and Gene Wilder, but it was successful enough it gave Hollywood the idea. To be honest, the premises of the three following Pryor-and-Wilder movies are so slim it is quite clear that they were thrown together to serve as vehicles for this pairing. The first of those is “Stir Crazy.” They play two innocent men who are thrown in prison. The two actors do their best to sell a half-baked script.

Technically, Ben Stiller and Owen Wilson are in “Meet the Parents” together, but that movie is about Stiller and Robert De Niro. It’s cult favorite “Zoolander” that first deployed them as a comedic duo. “Starsky and Hutch” is basically sold on “Stiller and Wilson in a spoof of that old TV show.” Honestly? It’s Todd Phillips’ best movie. That’s damning with faint praise, but it’s the case.

“Talladega Nights” is a Will Ferrell movie. John C. Reilly is in it, and the two have some fun chemistry, but it’s not really built on them as a duo. There was enough there for Adam McKay to cast them in “Step Brothers,” a good movie that gets a little too much love in general. Now, Ferrell and Reilly were a duo, they were notable costars. Interestingly, it took quite some time for the two to be cast together again. This time, it was in a riff on Sherlock Holmes and John Watson. Alas, “Holmes & Watson” is an atrocious movie. Not even reuniting Ferrell and Reilly could salvage it.

Before they were married (for the first time in two, speaking of being reunited), Richard Burton played Mark Antony to Elizabeth Taylor’s titular Cleopatra in one of the most infamous productions in Hollywood history. A couple years later, now married, Burton and Taylor were in a much smaller story, and a production that ran much smoother. Based on a play, “Who’s Afraid of Virginia Woolf?” has four characters total and essentially one location. Not every play is adapted to screen well, but this one was. “Who’s Afraid of Virginia Woolf?” got 13 Oscar nominations. Famously, all four cast members were nominated, with Taylor and Sandy Dennis winning.

Yes, the “Ocean’s” movies are ensemble movies, but there is a clear pairing atop that ensemble, and that’s George Clooney and Brad Pitt. They are both in peak movie star mode in those movies. Now, the two are reunited in a movie where they are the clear leads in what is clearly pitched as a Clooney-and-Pitt film. “Wolfs” sees the two as fixers who begrudgingly have to work together.