Sometimes the formula for success is right in front of you: if it ain’t broke, don’t fix it. The same goes with Hollywood, where stars frequently find themselves starring alongside each other again and again. This is no surprise: in the Golden Age of Hollywood (late ‘20s to 1960s), actors were usually contractually obligated to a studio. That means they were often cast in multiple movies with the same set of actors.
Fast-forward 50 years or so, and things are a lot more lenient. Most actors are now free agents - freelance workers who are more independent and can jump around to different studios. Many directors also cast the same actors in their films because they like the actors’ work (see: Tim Burton and Johnny Depp; Martin Scorcese and Leonardo DiCaprio; Judd Apatow and James Franco).
Oftentimes, real-life love interests become on-screen love interests, because it’s convenient for the actors - and possibly more believable for viewers - and directors. Other times, the box office draw potential of seeing two heavyweight stars side-by-side in a film is simply too irresistible for studios to ignore. Here are 14 pairs of actors who have starred in numerous movies with each other.
14 Seth Rogen and Jonah Hill
Seth Rogen and Jonah Hill are part of the “Apatow Chapter” of the Frat Pack - a group of comedic actors who have collaborated with and rose to fame with director Judd Apatow. The name is an allusion to the original Rat Pack. They are arguably two of the most successful comedic actors since the mid-2000s.
They have played roles (major and minor) alongside each other in seven movies, including The 40-Year-Old Virgin, Superbad, Knocked Up, as voice actors in Horton Hears a Who!, Funny People, This Is the End, and 22 Jump Street. Rogen had a cameo role in the latter film. Other frequent collaborators - and members of Apatow’s Frat Pack - are Paul Rudd, James Franco, Jason Segel, and Martin Starr.
13 Johnny Depp and Helena Bonham Carter
It is no wonder why Johnny Depp and Helena Bonham Carter have worked on many movies together. Johnny Depp is director Tim Burton’s favorite actor to shoot (my words, not his), while Carter is his girlfriend. They mainly appear together on-screen as love interests, in Burton’s typical dark/comedic/dramatic films.
The duo has appeared in six films together, including Charlie and the Chocolate Factory, Corpse Bride, Sweeney Todd: The Demon Barber of Fleet Street, Alice in Wonderland, Dark Shadows, The Lone Ranger, and a seventh, Alice in Wonderland: Through the Looking Glass is slated for release in 2016.
12 John Wayne and Ward Bond
For three decades, John Wayne was an American icon, and one of the top box office draws. He was the prototypical masculine man: rugged, calm, tall, and gritty. He became a mainstream star after his career took off in John Ford’s Stagecoach, and would go on to star in 142 films. He was best known for his Westerns, having played a cowboy in 83 of his films.
Wayne had frequent collaborators - a team of actors who would star alongside him - because directors knew the recipe for success was to have the Duke star alongside familiar faces. He appeared with Bruce Cabot in 11 films, with Paul Fix in 18 films, and with his most frequent collaborator, Ward Bond, in 22 films and two TV shows.
11 Sylvester Stallone and Dolph Lundgren
Sylvester Stallone and Dolph Lundgren have a rapport dating back to 1985, when Lundgren played the iconic Soviet Union boxer Ivan Drago against Stallone in Rocky IV, which was the most financially successful film in the Rocky series. Since then, they've shared the screen four more times.
Dolph was in archived footage (but uncredited) in 1990's Rocky V. He's also played a role in each of The Expendables films as the character Gunner Jensen.
10 Bruce Willis and Samuel L. Jackson
Bruce Willis and Samuel L. Jackson both have amazing careers playing action and dramatic roles. They were '90s megastars, and even in the Hollywood of the 2010's, they're huge draws at the box office. So what makes a film draw a crowd more than one superstar on the billing? Well, two superstars, of course.
They were first in a film together in the 1993 indie/action flick, Loaded Weapon 1. Their most iconic role together came the next next year in 1994, even though they hardly (if at all) shared screen time together. This film was Quentin Tarantino's Pulp Fiction. Coming off that success, Sam Jackson and Willis starred in Die Hard with a Vengeance a year later. Their final role together was in 2000's Unbreakable.
9 Simon Pegg and Nick Frost
These two plunky, funny Brits have made a career alongside each other. Simon Pegg and Nick Frost shot to fame with their widely-acclaimed action-comedy, Shaun of the Dead. They went on to finish what was called their Three Flavours Cornetto trilogy, which included Shaun, Hot Fuzz, and At World's End.
Almost all of the films they've done, they've done together (10 films overall). The other seven are Spider-Plant Man, Grindhouse , Nick Frost and Simon Pegg's Star Wars, Paul, and they've voice acted together in The Adventures of Tintin, Ice Age: Continental Drift, and The Boxtrolls.
8 Woody Allen and Mia Farrow
Woody Allen is a famed romantic comedy/drama writer and director, and he’s also starred in nearly all of his own movies. He frequently casts many of the same actors in his films, such as Diane Keaton, who starred alongside Allen in six of his movies. But his most frequent on-screen love interest is Mia Farrow, whom he starred in nine films with, mostly during the '80s.
The films with Allen and Farrow are A Midsummer Night’s Sex Comedy, Zelig, Broadway Danny Rose, Hannah and Her Sisters, Radio Days, Alphabet of Murder, New York Stories, Shadows and Fog, and Husbands and Wives. From 1979 to 1992, Farrow and Allen were partners, which is why she starred in nearly all of his films during this period.
7 Ben Stiller and Owen Wilson
Ben Stiller and Owen Wilson are part of the “original” Frat Pack - one generation removed from Apatow’s Chapter - which included some of the highest-comedies since the late 1990s. Other frequent collaborators and members of the Pack are Luke Wilson, Will Ferrell, Vince Vaughn, Jack Black, and Steve Carrell.
In all, Stiller and Wilson have appeared alongside each other in 11 films: The Cable Guy, Permanent Midnight, Meet the Parents, The Royal Tenenbaums, Zoolander, Starsky & Hutch, Meet the Fockers, Night at the Museum, Night at the Museum: Battle of the Smithsonian, Little Fockers, Night at the Museum: Secret of the Tomb. They are going to also star in 2016’s anticipated sequel, Zoolander 2.
6 Matt Damon and Ben Affleck
Matt Damon and Ben Affleck are good friends and prior schoolmates, and they’re even 10th cousins, once removed. Since their breakthrough role and Academy Award win for writing 1997's Good Will Hunting, they’ve both become two of Hollywood’s most bankable stars. Though they haven’t starred alongside each other in a film in around 10 years (they both went their separate directions), they still write alongside each other and produce movies together.
They have starred in nine films with each other, including Field of Dreams, School Ties, Glory Daze, Chasing Amy, their breakthrough Good Will Hunting, Dogma, Jay and Silent Bob Strike Back, The Third Wheel, Jersey Girl, and, as producers, have collaborated on Stolen Summer, The Battle of Shaker Heights, and Feast. They are frequent collaborators with writer and director Kevin Smith.
5 Humphrey Bogart and Bette Davis
Though it’s impossible to include every collaborative star during the Golden Age of Hollywood on a 10-part list, we decided to place two of the most important co-workers - and frequent collaborators - on it: Humphrey Bogart and Bette Davis. Bogey was the legendary Rat Pack leader who practically created the hard-boiled detective stereotype, while Bette Davis was his frequent on-screen lover and occasional femme fatale.
Bogart appeared with numerous leading ladies, but none more so than Bette Davis, whom he starred alongside in seven films during the '30s and early '40s. Those films are The Bad Sister, Three on a Match, The Petrified Forest, Marked Woman, Kid Galahad, Dark Victory, and Thank Your Lucky Stars.
4 Charlie Chaplin and Edna Purviance
As far as prolific collaborations goes, there is perhaps no greater duo than Charlie Chaplin and Edna Purviance. They starred as love interests in 33 films together (many of them shorts) in just an eight-year period, from 1915 to 1923. During this time, Charlie Chaplin was the most famous silent film actor (and actor in general) in the world. Since his films were so successful, he could basically choose any leading lady he wanted, and force the studios to have her star alongside him.
So, naturally, Chaplin chose the woman with whom he was romantically involved with to star alongside him. Her first film (after being scouted by one of Chaplin’s associates at a San Francisco cafe) was in A Night Out. She also starred in the 1921 classic, The Kid. Her last film with Chaplin, A Woman of Paris, was her first lead role.
3 Bradley Cooper and Jennifer Lawrence
Bradley Cooper and Jennifer Lawrence are all the rage in Hollywood these days. They're two of the fastest rising stars (J-Law is only 25) in the business, and they are frequent collaborators. All of their films end up being huge draws - and not just because of their names - but because of their superb acting skills.
They've starred in four films in each of the subsequent last four years, beginning with 2012's eight-time Academy Award nominated film, Silver Linings Playbook. Lawrence won the Best Actress Oscar for her performance, and Cooper was nominated as well. Since then, they've starred together in American Hustle, Serena, and Joy.
2 Robert de Niro and Al Pacino
Robert De Niro and Al Pacino are two of the most famous actors of the past 50 years. The two New York natives shot to fame by showcasing immigrant life in America, and gangster life. Then they went their separate ways. Though they’ve only starred in three films with each other, they are considered two of the greatest actors of all time, and together they are captivating.
Their first stint came in The Godfather: Part II, in which they never actually appeared together on-screen at the same time (different time periods). De Niro won the Academy Award for Best Supporting Actor for the film. Their next collaboration came with Michael Mann’s Heat, which was critically acclaimed for their joint performances. They also starred in the 2008 film, Righteous Kill.
De Niro has had frequent collaborations with other actors as well. He’s played in five films with Joe Pesci, including another Academy Award winner for De Niro, Raging Bull, and the highly acclaimed gangster films Once Upon a Time in America, Goodfellas, A Bronx Tale, and Casino.
1 Paul Newman and Robert Redford
Although they’ve starred alongside each other less than anyone else on this list (twice, if you’re counting), Paul Newman and Robert Redford practically helped coin the term “buddy film.” It would be impossible to include a list of actors who have starred in multiple movies with each other without including these two legends.
The two films they starred in were Butch Cassidy and the Sundance Kid, one of the most celebrated Western films of the era, and The Sting, one of the most celebrated con films of all time. Both were directed by George Roy Hill. The Sting was nominated for 10 Oscars and won seven, including Best Picture, Best Director, and Best Original Screenplay. Redford has stated that he had planned on starring in a third film with the late Newman, A Walk in the Woods, which was released in 2015.