Special Feature
From Frat Pack to Team Apatow: These Actors Keep Starring Together In Multiple Movies

Whether it is because of a long friendship, similar creative views, or just undeniably strong chemistry, some actors just can’t get enough of each other. From the historical “Rat Pack” who dominated Hollywood, to today’s new “Frat Pack”, these performers know what works and are experts at lighting up the screen with that irresistible chemistry. Check out our list of actors who have starred together in multiple movies.
1. Rob Schneider and Adam Sandler

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Before comedic actor Adam Sandler would become a household name, his friend Rob Schneider predicted his success. Sandler and Schneider met as aspiring comedians working in the improv comedy show world. The two later became cast members of the sketch comedy series Saturday Night Live, solidifying their professional, and personal, relationship.
Since working together on SNL, the two have appeared in more than 15 movies. While Sandler has focused on film, Schneider has returned to his stand-up roots, and has worked on a reality show for Netflix based on his life. Schneider feels thankful for the opportunities his friendship with Sandler has given him, saying, “He’s been nice enough to include me in his gigantic success story.”
2. Will Ferrell and John C. Reilly

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Actor John C. Reilly once joked that working alongside comedic actor Will Ferrell was “why we were put on this Earth”. The two have enjoyed a string of hits that have become comedy classics, with some of the most quotable dialogue in Hollywood.
While Reilly had a reputation for more serious films, his undeniable chemistry with Ferrell quickly showed that he was capable of flexing his comedy chops. Ferrell, a Saturday Night Live alum, met Reilly through actress Molly Shannon. The two starred in the race car parody film Talladega Nights: The Ballad of Ricky Bobby, the familial comedy Step Brothers, and as the iconic sleuthing duo Holmes & Watson.
3. Vince Vaughn and Owen Wilson

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In comedy, a familiar trope involves two seemingly different characters being forced to interact. For actors Vince Vaughn and Owen Wilson, there is truth in the adage “opposites attract”. The two actors have starred in multiple roles together, most notably their R-rated hit, Wedding Crashers.
Before Wedding Crashers, Vaughn had played mostly minor roles in Wilson’s films such as Starsky & Hutch, and Zoolander. Wedding Crashers proved that the two were an unstoppable comedic duo. Wilson has often stated that the two have “a different kind of energy”, which seems to create an inexplicable chemistry. Wilson has also commented on Vaughn’s collaborative energy, which made him feel comfortable exploring new ideas.
4. Margot Robbie and Will Smith

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When paparazzi images of Margot Robbie and Will Smith on the set of their crime dramedy Focus emerged, the pair’s chemistry had fans believing the two were having an off-camera affair. The film, which centered on a seasoned con artist and his equally cunning apprentice, showcased just how well the two worked on screen together.
While the two played a suave couple on camera, real-life interviews reveal a more down-to-earth relationship between the two actors, complete with ample teasing and joking around. In an interview with Hello magazine, Robbie mentioned that their effortless chemistry “wasn’t forced or planned, it just existed already which was handy”. The two later teamed up for the dark comic book film adaptation of Suicide Squad in which Robbie plays Harley Quinn, and Smith plays Deadshot.
5. Bradley Cooper and Jennifer Lawrence

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Bradley Cooper and Jennifer Lawrence are not only some of the most critically acclaimed actors in Hollywood; they’re also great friends off-screen. Their acting chemistry has resulted in the two actors receiving multiple awards and countless nominations. Cooper and Lawrence first appeared together in the drama Silver Linings Playbook, followed by the 1970s crime drama American Hustle, the romantic western Serena, and the drama Joy.
Lawrence has frequently praised Cooper; she remarked “the first time we ever did a scene together, you took my breath away.” To his credit, Cooper has also heaped on the praise, saying, “I feel very safe [with Lawrence]. I can turn my brain off as an actor.” Given the amount of awards between the two, it’s safe to say that audiences will be seeing more from this acting pair for years to come.
6. Brad Pitt and George Clooney

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While both actors may have been dubbed People magazine’s Sexiest Man Alive, Brad Pitt and George Clooney’s bond runs much deeper than magazine accolades — or the fact that they are both Academy Award winners for Best Supporting Actor. Pitt and Clooney have starred in six feature films together, and have appeared together in a variety of projects.
The acting duo’s most famous joint venture has been the Oceans crime comedy series. In the Las Vegas casino heist film, the two play suave thieves hoping to pull off the ultimate crime. Off camera, the two have enjoyed a friendship over the years which began after meeting on the set of Ocean’s Eleven in 2001. The two remain supportive of each other’s projects, with Pitt even landing a cameo role in Clooney’s film, Confessions of a Dangerous Mind.
7. Kristen Stewart and Jesse Eisenberg

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While Kristen Stewart may be famous for playing the love affection of a vampire in the Twilight series, it is her subtle chemistry with frequent costar Jesse Eisenberg that has left many fans excited at seeing the acting duo onscreen. The two first appeared together in the coming of age dramedy, Adventureland. Fans and critics enjoyed Eisenberg and Stewart’s realistic interpretation of teen love.
The duo then starred in American Ultra, an action comedy film in which Stewart and Eisenberg play an ordinary couple wrapped up in a government conspiracy. Stewart has often praised her good friend and costar, saying that that she immediately signed up for the role of Eisenberg’s love interest in Woody Allen’s Café Society upon hearing he would be involved.
8. Tina Fey and Amy Poehler

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Before they were making audiences laugh on Saturday Night Live, Tina Fey and Amy Poehler were aspiring comedians flexing their improvisational muscles at Chicago’s ImprovOlympic Theater class. In her memoir Yes, Please, Poehler said that her first interpretation of Fey was that she “was sharp, shy, and hilarious”.
The two later went on to star in, and write for, the comedy sketch series Saturday Night Live. The acting duo became famous for their roles in the cult comedy Mean Girls, the beginning of their film collaborations. The two next appeared in the comedies Baby Mama, Sisters, and Wine Country. Poehler continues to work with Fey, and believes that they have a special bond beyond show business, saying: “I think that Tina and I are chosen sisters.”
9. Ryan Gosling and Emma Stone

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For actors Emma Stone and Ryan Gosling, the zany comedy Crazy, Stupid, Love would be the beginning of an acting love story that would span across multiple movies. Following the romantic comedy, the two starred in Gangster Squad and the critically acclaimed La La Land.
Many critics believe that the duo’s undeniable chemistry is behind their award-winning performances. Stone has often referred to Gosling as a “wonderful friend”, and has even stated: “I can’t even imagine what my life would be without Ryan.” Gosling has also professed his appreciation, saying “There’s nobody like her.” While collecting an award at the BAFTA Awards, Stone emotionally told audiences that her costar “elevates everything he touches”.
10. James Franco and Seth Rogen

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Goofy actors James Franco and Seth Rogen have showcased their friendship by starring together in more than ten films. Throughout their multiple movies, the two have created their own brand of comedy, which many believe reinstated the popularity of R-rated comedies in Hollywood.
The two met on the set of the high school comedy show Freaks and Geeks, but their relationship really developed while filming Pineapple Express in 2007. From that moment, the two have appeared in wacky comedy flicks like The Interview, This is the End, and The Night Before, as well as more serious films such as The Disaster Artist. The two are good friends, and frequently collaborate with one another, even just as cameos in each other’s films.
11. Matt Damon and Ben Affleck

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One of the most celebrated acting pairs that have appeared in multiple movies are Matt Damon and Ben Affleck. Before winning their Oscar for Best Original Screenplay, the two were young actors who grew up in the same Boston-area neighborhood. In addition to roles as extras on the set of Field of Dreams, the two appeared in School Daze and School Ties.
Affleck and Damon have often mentioned how they supported one another before striking it big with their 1997 film Good Will Hunting. They continued to work in other films such as Chasing Amy, Dogma, The Third Wheel, the Jay and Silent Bob series, and the critically-panned film Jersey Girl. The two will return to their writing roots with the film adaptation of the historical novel, The Last Duel.
12. Ben Stiller and Owen Wilson

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One of the best known comedy duos in movies these days would have to be Ben Stiller and Owen Wilson. The two have a rich history of acting together in multiple films, and supporting one another’s projects. Their relationship began when Wilson starred in Stiller’s film, The Cable Guy. Stiller also sent Wilson a letter praising his film Bottle Rocket, which Wilson co-wrote.
Wilson and Stiller later went on to star in the dark drama Permanent Midnight, before the duo starred in one of their most famous roles as exes in Meet the Parents. Following their success in that comedy, the two joined forces for the commonly quoted comedic classic Zoolander. The two continued their onscreen relationship in the films The Royal Tenenbaums, Starsky & Hutch, Meet the Parents sequels, the Night at the Museum series, and a Zoolander sequel.
13. Timothée Chalamet and Saoirse Ronan

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For many audiences, Timothée Chalamet and Saoirse Ronan are quickly emerging as one of the most powerful acting duos of this generation. The two award-winning actors first joined forces on the set of the film Lady Bird. Director Greta Gerwig knew that the two possessed great chemistry, and cast both actors in her screen adaptation of the classic novel Little Women.
Following the critical success of their films, the two actors have nothing but praise for one another. In an interview with Entertainment Weekly, Ronan stated that Chalamet “keeps me on my toes”. Director Greta Gerwig has compared their chemistry to a “bonfire” and says “when you put them together it’s like combustion”. The two will appear together again in the film, The French Dispatch.
14. Drew Barrymore and Adam Sandler

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Actress Drew Barrymore frequently compares her first meeting with comedic actor Adam Sandler to a bad date. Despite their initial differences, the two found that they possessed a similar sense of humor, which would lead to them making multiple movies together.
The two first appeared onscreen in the ’80s-themed romantic comedy, The Wedding Singer. Years later, they starred as an onscreen couple in the comedies 50 First Dates and Blended. Barrymore even dedicated a chapter to him in her memoir, Wildflower. While presenting Sandler with an award, she gushed, “You deserve the best, you give the best and you are the best.” The two have often hinted that they will be working together again on another film for Netflix.
15. Johnny Depp and Helena Bonham Carter

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Johnny Depp and Helena Bonham Carter are known for their often eclectic and unique roles. Depp and Carter first appeared in the macabre animated film Corpse Bride, and later in the screen adaptation of Charlie and the Chocolate Factory. Both films were directed by Carter’s ex, Tim Burton.
The trio continued to collaborate on other films, including the dark musical Sweeney Todd: The Demon Barber of Fleet Street, adaptations of the novel Alice in Wonderland, the Gothic vampire film Dark Shadows, and Depp’s Western The Lone Ranger. As longtime friends, Depp continues to maintain a relationship with the separated couple. While Carter’s relationship with Burton may have ended, she assures fans that Depp will continue to work with the eccentric director saying, “Nothing will separate them.”
16. Shailene Woodley and Ansel Elgort

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For most actors, the thought of going from siblings to playing lovers can be a difficult process. Yet for actors Ansel Elgort and Shailene Woodley, their chemistry helped prepare them for a drastically different role. The two first appeared in the movie Divergent, a film adaptation of the sci-fi young adult series of the same name.
In the film, Elgort plays Woodley’s brother, a relationship seen across the series’ multiple movies. Elgort and Woodley, who developed a close friendship on the Divergent set, went on to star as lovers in the teen drama The Fault in Our Stars. Woodley told Time magazine: “Ansel and I have an affinity for each other just as far as recognizing and admiring the spirits in one another.” The two are often photographed together, and have publicly praised one another.
17. Stanley Tucci and Meryl Streep

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For many fans of the movie Julie & Julia, one of the most memorable parts of the film is the relationship between Julia Child (played by Meryl Streep) and her husband Paul Child, played by actor Stanley Tucci. Tucci and Streep’s chemistry was highly praised, and is the result of a real-life friendship with the actor.
Tucci revealed that while preparing for the role, he and Streep would often practice cooking together. The two actually worked together before in the acclaimed fashion flick The Devil Wears Prada, in which Streep plays the intimidating editor of a women’s magazine, and Tucci plays an art director. Streep has praised Tucci by saying: “I’ve been in love with him from a far anyway with the totality of the man from Big Night to his directing work, in every way.”
18. Scarlett Johansson and Chris Evan

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Before Scarlett Johansson and Chris Evans were zipping up their superhero costumes for their roles in Marvel’s Avengers films, the two crossed paths on the set of the teen comedy The Perfect Score. Following that role, the two played a couple in the comedy The Nanny Diaries.
The pair, who became close friends, have appeared in multiple movies in the Marvel Cinematic Universe. As main characters Black Widow and Captain America, the two have starred in more than half a dozen Marvel films. Johansson told the L.A. Times, “We work well together, I think, and admire one another as actors.” Fans of the comic book series agree: Black Widow’s relationship with Captain America remains a fan favorite.
19. Al Pacino and Robert De Niro

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For most film critics, no list of ‘great film actors’ would be complete without the mention of legendary actors Al Pacino and Robert De Niro. The acclaimed actors have created their own legacies individually, but when combined, many believe, true cinematic magic can be achieved.
The two first appeared in Coppola’s mafia classic, The Godfather II, but did not share scenes together. This was corrected when they appeared in the crime film Heist. Their memorable scenes in the adrenaline-pumping movie led to their reunion in Righteous Kill. Their most-talked about on-screen appearance, however, was in Scorsese’s 2019 film The Irishman. The film, about the criminal underworld, was heavily lauded by movie critics.
20. Tom Hanks and Meg Ryan

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Meg Ryan and Tom Hanks became household names as the stars of some of the most well-known and beloved romantic comedies of the 1990s. What many people do not know is that their on-screen relationship began with a lesser-known romantic comedy called Joe Versus the Volcano. While the movie received mixed reviews, the acting duo’s chemistry did not.
Hanks and Ryan continued to develop their acting chemistry on the sets of multiple movies like Sleepless in Seattle and You’ve Got Mail. The acting pair, who are close friends in real life, have often praised each other. Hanks admires his frequent costar, saying in a 1998 interview, “I always feel as if I have to be on my toes around Meg.” Hanks is so supportive of Ryan that the two reunited on screen for Ryan’s 2015 directorial debut, Ithaca.
21. Woody Harrelson and Matthew McConaughey

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Woody Harrelson and Matthew McConaughey have enjoyed one of the longest lasting friendships in Hollywood. The two met on the reality show satiric film Edtv, followed by their surf themed comedy Surfer, Dude. While the two have enjoyed success in more lighthearted films, both actors have increasingly explored darker themes in multiple movies.
Harrelson and McConaughey received critical praise for their roles in the HBO crime drama True Detective. While the two actors are close friends in real life, their characters are vastly different homicide detectives forced to interact as they attempt to solve a case. In preparing for the role, McConaughey said that he had to force himself to see Harrelson as “not being on each other’s frequency” in order to accurately portray the often combative characters.
22. Maya Rudolph and Kristen Wiig

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Maya Rudolph and Kristen Wiig are considered some of the funniest comedic actors in Hollywood. These Saturday Night Live veterans have gone on to make audiences laugh with multiple movies and projects. One of the acting duo’s greatest hits was their 2011 breakout hit, Bridesmaids.
Rudolph, who plays the bride-to-be, is actually one of Wiig’s close friends. Filmmakers wanted to cast Rudolph because the chemistry between the women added to the script. The two later starred in a film exploring friendship in the comedy Friends with Kids. Rudolph and Wiig’s appearance at the 2020 Oscars became one of the most talked-about moments in pop culture, cementing their reputation as one of Hollywood’s most talented duos.
23. Zoë Kravitz and Shailene Woodley

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From dystopian alien landscapes to suburban California, Shailene Woodley and Zoë Kravitz’s acting chemistry has garnered the attention of many film critics. Kravitz first appeared alongside Woodley in the science fiction film Divergent. The two reunited in the series’ sequels Insurgent and Allegiant.
The two were later cast as women brought together in a small town in Northern California in the show Big Little Lies. Kravitz was ecstatic that her former costar would be joining the cast of the drama, saying, “We are obvious soulmates and the universe agrees, because we keep on getting put together, which is fantastic.” The critically acclaimed show, which focuses on the friendships between a group of women, helped bring Woodley and Kravitz even closer together.
24. Leonardo DiCaprio and Kate Winslet

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One of the most iconic images in modern cinema is the image of Kate Winslet and Leonardo DiCaprio embracing on the hull of the doomed ocean liner, the Titanic. The film, Titanic, not only helped launch the careers of Winslet and DiCaprio, but it was the beginning of a life-long friendship between the two actors.
Winslet admitted that she was initially intimidated by her co-star’s good looks, and worried that a romantic situation between the two would affect their performance. Luckily, that wasn’t the case, and the two remain close friends decades after the blockbuster hit. They reunited on-screen for the 1950s drama Revolutionary Road. In an interview, the two admitted they were excited to be acting alongside one another again, with DiCaprio saying, “It’s a great to work with one of your best friends.”
25. Kate Hudson and Matthew McConaughey

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One of the most popular romantic comedies in recent decades was the 2003 hit How to Lose a Guy in 10 Days. The film, which starred Kate Hudson and Matthew McConaughey, became a fan-favorite due to the obvious chemistry between the two leads.
While Hudson and McConaughey may act romantically on screen, their real-life relationship is far more platonic. Hudson has joked about her former co-star’s refusal to wear deodorant, while he has joked she can’t keep track of time. Audiences and critics, however, have praised their palpable chemistry so much that the pair reunited in the buried treasure themed comedy, Fool’s Gold. McConaughey recently reflected on his work with Hudson, saying: “Kate and I had great chemistry.” Clearly, fans agree.
Sources: People, Toronto Sun, USA Today
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