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The Best Screen Pairing of Each Decade

Tucker Guillot
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In many ways, actors are the face of the movie industry. To the average audience, producers, writers, and directors are often inconsequential to increasing a movie's appeal. However, if even the most average looking film has a major star like Tom Hanks or Margot Robbie, people will see it.

Of course, it takes more than solid acting to make a great film. However, the actors are the easiest to sell in a short trailer, rendering them crucial to a film's success.

As such, films must really nail their cast if they want a chance at the box office. Sadly, not every film does this, as this year's Snow White can attest to. But when a film does cast well, it can not only yield immediate success, but also leave an impact that'll stick with audiences for years.

As such, I thought it would be interesting to look at some of the greatest casting choices of cinema history. Instead of just focusing on one role though, I'm aiming to find the absolute best screen pairing from each decade starting with the 1920's.

The criteria for what makes a great screen pairing involves a few aspects, the first one being on screen chemistry. Whether the duo are romantic or not, they must act well together, almost becoming a force themselves.

Speaking of which, both actors in the pair must have inherit talent. Sure, these all come from some of the finest films of all time, but the higher the actors' pedigree, the more appeal they garner.

Some of these pairs might have been in multiple films together, although it's not required. What each pair must have in common though is that they share the screen often enough to establish a true relationship. It can be as lovers, friends, enemies, or some combination, but they must form a relationship that's absolutely enthralling.

Lastly, if I haven't seen a movie, I can't include it, even in the honorable mentions. That being said, here are the screen pairings that I found the most exciting, intense, and iconic of each decade.


1920's: Charlie Chaplin and Mack Swain in The Gold Rush (1925)

Honorable Mentions: Max Shreck and Greta Shroder (Nosferatu), Buster Keaton and Marion Mack (The General), George O'Brien and Janet Gaynor (Sunrise)

Across his career, Charlie Chaplin developed quite a few on screen romances worthy of merit. However, for the 20's, his best on screen pairing comes from The Gold Rush, where he portrayed the prospecting bromance with Mack Swain.

In this silent film, Chaplin plays a version of the Little Tramp who's looking for gold in the Alaskan wilderness. There he runs into Big Jim McKay (Swain), a larger than life prospector who has no problem forcing his will onto others.

Despite being friends for most of the film, the Tramp and McKay have quite the tumultuous relationship. They are initially allies, but once they become trapped in a cabin without food, they both start to break mentally. McKay imagines the Tramp as an immense chicken, while the Tramp in turn grows paranoid. This culminates in a wacky chase scene, that leads to the death of a bear, which solves the duo's hunger problem.

Yet, the duo also have moments that attest to their fine friendship. They eventually return to the cabin, but find themselves hanging off the side of a cliff the next morning. Both nearly fall to their deaths a few times, but using each other's strength, they're able to defeat gravity and find their gold moments later.

What makes Chaplin and Swain such a pleasure to revisit is that their entire relationship is presented through physical comedy. Without sound, the onus of presenting this relationship falls entirely on the duo. Chaplin unsurprisingly delivers with his signature wacky physical humor, but Swain truly holds his own against the Tramp's frenetic energy. Towering over the Tramp, Swain is his physical foil, fighting other men while the Tramp hides.

Each actor dominates the screen in their own way, and the union feels completely synergetic. For each odd expression Chaplin throws out, Swain throws back a madman's stare, showing the dichotic attitude both bring to prospecting. As such, we are treated to an iconic friendship, two men who don't really match each other in any way besides their desire to find gold.


1930's: Ginger Rogers and Fred Astaire in Swing Time, Top Hat, and seven more films

Honorable Mentions: William Powell and Carole Lombard (My Man Godfrey), Cary Grant and Katharine Hepburn (Bringing Up Baby), Clark Gable and Vivien Leigh (Gone with the Wind), Clark Gable and Claudette Colbert (It Happened One Night)

As cinema itself evolved in the 30's, so did the screen pairings. Now strapped with the advantage of sound, 30's films delivered some truly swoon worthy romances, many of which would be fine picks here. However, no actors took advantage of both the audial and visual components of film with nearly as much chemistry as Ginger Rogers and Fred Astaire.

During the 1930's, Rogers and Astaire starred in an astounding nine films together. Through these productions, the pair became synonymous with Hollywood showmanship, flirtatiously singing and dancing in just about every film. In fact, the pair are nearly synonymous with dancing, as their toe tapping rhythm kept bringing in audiences for the entire decade.

If you've seen any of their films, you'll know the intensity they bring to their craft, as well as the romantic tone they easily set. Yet, what's often under appreciated about this duo is how well they keep up with each other. Yes, both actors are incredibly talented, but it's their capacity to remain synchronized with each other, whether they be dancing, arguing, or kissing, that makes them so engaging.

For instance, in their finest film, Swing Time, Astaire and Rogers play enemies turned lovers. They dance, of course, stealing every scene they're in, but they don't stop there. They also fight like lovebirds, berating each other in a physical rhythm only that feels like a dance in and of itself. No matter what the pair do, they feel intrinsically connected and the romance is all the better for it.

In a way, only Rogers can match the charm and skill that Astaire brings to the silver screen, making them a perfect fit. Rogers and Astaire are not legends because they made a lot of films together, but rather their legendary chemistry was worthy of so many films.


1940's: Humphrey Bogart and Ingrid Bergman in Casablanca (1942)

Honorable Mentions: Henry Fonda and Jane Darwell (The Grapes of Wrath), Fred MacMurray and Barbara Stanwyck (Double Indemnity), James Stewart and Henry Travers (It's A Wonderful Life)

Sometimes the obvious pick is the right one, especially when it comes to casting. As is often the case, the winner here is Casablanca, which gave audiences the all time great pairing of Humphrey Bogart and Ingrid Bergman.

The premise of Casablanca is pretty well known, but the actual relationship Bogart and Bergman must play into is more complex. In the film, Rick (Bogart) and Ilsa (Bergman) were once lovers and part of the resistance against fascist Germany. However, Ilsa deserted Rick, leaving him a jaded and apathetic man. They cross paths again, as Ilsa needs Rick to help her escape with her new husband, an important resistance leader. Their encounter brings up feelings of both grief and passion, but Rick sends Ilsa away before she can fall for him again.

Playing a great romance is hard, but that's not what Bogart and Bergman do here. Instead, they must play reflections of a relationship, one that was romantically vibrant, but has scarred both parties. What was once young love is now bitter residue, rife with regret that eats at Rick' moral obligations. It almost teeters back to true romance, but Rick's morality takes over at the very end.

Bogart and Bergman excel at every step of this rickety relationship. Even before Ilsa is introduced, the disdain is clear in Rick's expressions, showing that something from his past still haunts him. When that something shows up in person, Bogart leans into Rick's anger, voicing his outrage and dismay as he realizes this part of his life isn't over yet.

As for Bergman, she embodies a woman in constant turmoil, struggling between her love for Rick, her commitment to her husband, and her own moral leaning. Soon, the duo fall for each other again, allowing Bogart and Bergman to play into their chemistry, culminating in perhaps the greatest scene in cinema history.

However, that final goodbye only works because Bogart and Bergman shows us the pain that this relationship has struggled through, allowing us to hope just for a moment that they might make it out together.


1950's: Audrey Hepburn and Gregory Peck in Roman Holiday (1953)

Honorable Mentions: William Holden and Gloria Swanson (Sunset Boulevard), Bette Davis and Anne Baxter (All About Eve), James Stewart and Grace Kelly (Rear Window), Charlton Heston and Stephen Boyd (Ben-Hur)

Truthfully, the 1950's had no shortage of superstar pairings. Older stalwarts shared the screen with rising stars, and the results spoke for themselves. Nowhere is this better exemplified though than in Roman Holiday, which pairs Gregory Peck with a then unknown Audrey Hepburn.

On the surface, Roman Holiday offers a pretty standard romance. Peck plays Joe Bradley, a reporter in Rome in need of a big score. When he encounters fugitive Princess Ann, played by Hepburn, they end up spending the day together. However, they fall in love and romantic hijinks ensue.

With a straightforward love story, Hepburn and Peck play their halves of this couple spectacularly. Whether they're riding scooters, fighting on the riverside, or sharing looks of passionate longing, both actors foster an authentic relationship that's magical in its own right.

Yet, it's that cross section of fame between Peck and Hepburn that makes their relationship so captivating. Peck was already famous at the time, starring as a heartthrob in a variety of successful films. However, this film would be Hepburn's introduction to the world, placing a large onus on her end. She would knock it out of the park (hence her Oscar win), but it's still an impressive act of casting.

Still, by pairing an established, likable actor with a young, talented actress, Roman Holiday delivers a fresh, vibrant romance. Peck feels like a sturdy reliable man, one you wouldn't mind being lost in Rome with, while Hepburn fulfils the youthful face of someone who's truly living for the first time in their life.

This is best captured in the Vespa scene where Ann hijacks a scooter to run from the cops. As Joe's face looks terrified, Anne laughs and smiles her way through it, allowing the freedom to propel her through the Roman streets.

It's a whirlwind romance for the ages, one both parties know must end. But the beauty doesn't come from true love. Instead, the beauty is derived from a vivacious encounter we could never expect nor dream of, which is presented strikingly here by Hepburn and Peck.


1960's: Paul Newman and Robert Redford in Butch Cassidy and the Sundance Kid (1969)

Honorable Mentions: Warren Beatty and Faye Dunaway (Bonnie and Clyde), Dustin Hoffman and Jon Voight (Midnight Cowboy), Cary Grant and Audrey Hepburn (Charade), Julie Andrews and Christopher Plummer (The Sound of Music)

Butch Cassidy and the Sundance Kid is another one of those movies I've talked about a lot, mostly because it was the first Western film I truly adored. The film offers a lot, such as its stellar cinematography, but it never would've achieved cinematic notoriety without its main duo Butch Cassidy and the Sundance Kid played by Paul Newman and Robert Redford.

Although the pair portray notorious outlaws, the heart of the story resides in their friendship. For every scene of a train robbery or shootout, there's one where they're riding bikes in the sun enjoying their lives. No matter what they pair do, they do it as one and they do it well.

Still, this friendship is best felt in the comedic barbs Cassidy and Sundance shoot back and forth at each other. Delivered with impeccable timing, nearly every scene features a joke between the two, attesting to the duo's comfort and understanding. Even when they seem doomed, the pair continues to crack jokes, showing how in sync their jesting mentalities are.

That's not to say that the pair never fights, as there are a few intense moments between the two. However, it's their lighthearted understanding of each other that makes them so remarkable. By the end of the film, it's clear that Newman and Redford are perfect for these roles, as their timing and chemistry make it seem like they're hardly acting at all.

In fact, the pair seem to live up to the legends they portray a few times over. While a number of actors could've played badass cowboys, Newman and Redford played humans. Cassidy and Sundance tell jokes, hang out, and make mistakes. Sure, they kill people too, but the men beneath the hats are all the more relatable thanks to the pathos each actors brings.

With two affable leads, the film is able to tell its compelling story about the fleeting world of the West. Although these heroes are quite different, their connection is unmissable, and their friendship seems eternal in an era that's already doomed.


1970's: Woody Allen and Diane Keaton in Annie Hall (1977)

Honorable Mentions: Al Pacino and Marlon Brando (The Godfather), Jack Nicholson and Faye Dunaway (Chinatown), Dustin Hoffman and Robert Redford (All the President's Men), Robert De Niro and Christopher Walken (The Deer Hunter)

Many consider the 70's to be the decade of the auteur, but it also boasted some of the finest actors of all time. De Niro and Pacino got their careers rolling, while the likes of Nicholson, Brando, and Hoffman further cemented their resumes. However, it's tough to find an on screen pair with more chemistry than Woody Allen and Diane Keaton in Annie Hall.

One of the most depressingly humorous romance films, Annie Hall tells the story of neurotic Alvy (Allen) and his up and down relationship with the titular Annie Hall (Keaton). We get to see the highs and lows of a complex romance, one constantly teetering between Hollywood euphoria and complete implosion. It ends closer to the latter, as both Alvy and Annie end up moving on to someone else.

For most of the film, Alvy remains at the center, as we explore his troubled history with love starting in elementary school. However, it's his relationship with Annie that lets Alvy work through his crisis, as it reminds him of the torture he puts himself through in pursuit of love.

When we first meet Annie, she seems like a dream girl, someone worth spiraling into crisis for. She's funny, but a little awkward, driving erratically and using her own saying. She's both spontaneous and stylish, which is why Alvy immediately becomes attracted to her. It's a fantastic meeting, one that allows Allen and Keaton to romanticize that first encounter to the point that it's a critical moment in Alvy's life.

Later though, we get to see more of the couple's intimate moments. They sleep together, smoke together, and, eventually, fight together. These scenes stand out in such a funny movie, especially with the dread that each disagreement entails. Allen and Keaton prove they can bicker with the best of them, as Alvy's pretentious banter clashes against Annie's pent-up frustration. Most of all though, these scenes show that both parties are imperfect, which feels far more realistic than what Hollywood traditionally offers.

As the movie ends, we get a true sense of what romance entails. Allen and Keaton sell both the dreamier moments, such as their lobster fight, and the bitter lows they eventually sink to. Allen argues that romance, while painful, is worth seeking, and the film as a whole attests to that sentiment completely.


1980's: Dustin Hoffman and Tom Cruise in Rain Man (1988)

Honorable Mentions: Harrison Ford and Carrie Fisher (The Empire Strikes Back), Michael J. Fox and Christopher Lloyd (Back to the Future), Billy Crystal and Meg Ryan (When Harry Met Sally), Wil Wheaton and River Phoenix (Stand By Me)

By the time the 1980's rolled around, Dustin Hoffman was already Hollywood royalty. He had starred in several classics, won an Oscar, and even acted in some iconic duos worthy of this list. Still, his crowning achievement might be his work in 1988's Rain Man, where he portrays Tom Cruise's mentally disabled brother.

The first actual pair of brothers on this list, Charlie (Cruise) and Raymond (Hoffman) couldn't be any more different. Charlie is a self centered workaholic, always pursuing his best interest, which in this case is his father's inheritance. But Charlie's not a flat character, as he's wrestling with inner anguish and frustration left over from his fractured relationship with his father. The revelation of a secret brother is only the cherry on top, leaving Charlie unbalanced and overtly angry.

In contrast, Raymond is a man at peace. Of course, he has his intricacies and quirks, such as needing to watch his shows at the same time every day. However, as long as he keeps to his schedule, Raymond is content.

Also, Raymond exhibits an incredible gift for counting numbers almost to a superhuman extent. While Charlie struggles to maintain his business or exhibit any real skills, Raymond is talented beyond understanding.

With such different brothers, both actors give quite different performances that are great in their own right. Hoffman plays Raymond with accurate respect, capturing the intricacies and mannerisms someone different. Cruise also gives a tremendous performance, often lashing out and failing to understand Raymond's needs. The emotions he unearths here are gripping, making it one of Cruise's best acting displays.

Most of all though, the evolution of Charlie and Raymond from strangers to brothers will move most viewers with ease. Despite the predictable plot, the duo's brotherhood is gradually built up so that their final goodbye prompts genuine heartache. Cruise plays a good asshole and Hoffman plays a great handicapped man, which leads to many cringeworthy clashes early on. However, by the film's end, there's no doubt that they see each other as brothers.


1990's: John Travolta and Samuel L. Jackson in Pulp Fiction (1994)

Honorable Mentions: Morgan Freeman and Tim Robbins (The Shawshank Redemption), Brad Pitt and Edward Norton (Fight Club), Leonardo DiCaprio and Kate Winslet (Titanic), Robert De Niro and Joe Pesci (Goodfellas and Casino)

In retrospect, Tarantino has always had a knack for great casting. He's cast well known actors in imaginative roles, such as Kurt Russell as a killer stuntman or Mike Myers as an army general. He's also discovered a plethora of talents such as Christoph Waltz and Margaret Qualley. However, his finest casting choice might just be bringing John Travolta and Samuel L. Jackson together in Pulp Fiction.

In Tarantino's second film, Travolta and Jackson play two hitmen who cross in and out of LA's world of crime. Although they're not the focus of the film, they act as its main driving force, and many of the film's storylines circle their exploits.

As the movie's nonlinear narrative progresses, we get a sense that they share a unique bond. They're not brothers, but the violence they carry out has welded them together in a way that true brotherhood never could. As such, they move in sync with each other and prove that they're at the top of their game.

However, Jules (Jackson) encounters a crisis of faith and realizes he must leave the business. After a miraculous survival, Jules becomes enamored with fate and believes he has some higher calling than killing.

The same cannot be said for Vincent (Travolta), who has no problem with this line of work. He enjoys the sins of his life, killing when he needs to and abusing a variety of drugs. As such, the pair hit a crossroads and must split. We never get to see Jules' fate, but Vincent's life of debauchery leads him to a brutal fate that officially ends their brotherhood.

Still, the pair wouldn't have been compelling without Tarantino's all time great casting. Jackson had been in films before, but his talents had never been channeled like they are here. As for Travolta, his career had pretty much tanked, with everyone assuming he was done acting.

Yet, Jackson's fresh vitality brought the best out of Travolta, allowing each to find the role of a lifetime. With their great dialogue exchanges and balance of intensity, Jules and Vincent provide quite the entertaining duo. Whether they're eating, driving, or killing people, they do so in unison and exquisite style.


2000's: Leonardo DiCaprio and Kate Winslet in Revolutionary Road (2008)

Honorable Mentions: Christian Bale and Heath Ledger (The Dark Knight), Russel Crowe and Joaquin Phoenix (Gladiator), Mike Myers and Eddie Murphy (Shrek franchise), Ian McKellen and Patrick Stewart (X-Men franchise)

As expected, nearly every screen pair on this list comes from a surefire classic. It only makes sense, after all, that the best on screen duos come from the best films.

However, few would call Revolutionary Road a classic. While incessantly searing and sickeningly dramatic, the film never quite found its cultural footing. Still, it boasts an already iconic screen pairing, Leonardo DiCaprio and Kate Winslet, this time as a struggling married couple in the mid 50's.

Obviously, DiCaprio and Winslet are best known for Titanic, which showed their endless chemistry and capacity for romance. However, their characters, Frank and April Wheeler, encounter a different disaster here, a marriage that just won't work.

In the beginning, April and Frank fall for each other's spontaneity and vivacity. With a young naivety, they're ready to see the world together and lead adventurous lives. Years later though, that spark is gone. April grows tired of being a housewife, especially as her Frank becomes unfaithful. She yearns to leave suburbia, but Frank resists, as he's settled into ordinary life. They almost make it out, but April becomes pregnant and the pair call it off, eventually leading to her death.

Due to the pair's talent, every scene becomes an emotional overload. Frank and April duel with passion, arguing viciously until they've both been dismantled. From DiCaprio's aloof complacency to Winslet's desperate fight for help, both actors fulfill the toxicity needed for such an awful couple.

Of course though, what's most jarring about Revolutionary Road is how much it plays against Titanic. After seeing DiCaprio and Winslet play such a legendary romance, watching them relentlessly quarrel and suffocate each other becomes a jarring experience.

In fact, the characters of Frank and April feel like poor versions of Jack and Rose. Frank initially claims to be spontaneous, but lacks the courage to actually go on an adventure like Jack. Frank's also completely unfaithful, which pales to Jack's undying fidelity. Meanwhile April can never muster up the courage to leave Frank like Rose does with Cal. As such, Frank and April are poor shadows of Jack and Rose, never completing their arcs or living up to the grand expectation of romance.

With more flawed characters, Revolutionary Road sinks its teeth into the bitter taste of romance in a perhaps more realistic way. People waited nearly a decade to see DiCaprio and Winslet reunite and received one of the most dramatic pieces of melancholia of all time.


2010's: Ryan Gosling and Emma Stone in Crazy, Stupid, Love, La La Land, and Gangster Squad

Honorable Mentions: Robert Downey Jr. and Chris Evans (MCU), Jesse Eisenberg and Andrew Garfield (The Social Network), Natalie Portman and Mila Kunis (Black Swan), J.K. Simmons and Miles Teller (Whiplash)

Despite being a bit of a mixed bag, the 2010's didn't disappoint with its onscreen pairings. Most of these actors are still young, but they found their grooves as superhero teammates, complex lovers, and rivals at the height of their artistic craft. Still, no actors really clicked together as much and as often as Ryan Gosling and Emma Stone.

Gosling and Stone's pedigree needs little introduction, as their work is well known among cinephiles and fans alike. They starred in the cutting rom com Crazy, Stupid, Love before reuniting for Gangster Squad and then cementing their legacy with perennial favorite La La Land. With such palpable chemistry, Gosling and Stone often play lovers, portraying swoon worthy romances with humor and passion. Even more, the duo are friends in real life, often playfully crossing paths at big Hollywood events, such as last year's Oscars.

As such, Gosling and Stone have been one of the decade's inarguable highlights. Even as they develop their own stupendous careers, which include box office hits and Oscar wins, both will always be known for their collaborative success.

Each of their films reflects their innate chemistry, but it's La La Land that remains their finest work. In the film, the duo dance and sing their way from enemies to lovers to complete strangers. With carefully composed choreography and witty, romantic banter, the pair live up to the classic Hollywood stars they emulate. Most of all though, they fulfill an idealized romance, one that could only happen in Hollywood. Of course, that cinematic pureness is fleeting and the film ends with them on separate paths.

In the film's final moment, Mia (Stone) departs Sebastian's (Gosling) club and turns to give him one last look of longing. With their eyes clearly in focus, their souls lock together, almost insisting that they belong together. But reality steps back in, and Mia departs, accepting each of their fates.

It's a moment that recontextualizes the entire film, and it's perfectly played by its duo. While it may only seem like longing, Stone and Gosling stare as if every force in the world is compelling them to run to each other. After watching them fall in love in the colorful world of Los Angeles, it seems like they might reunite one last time, even though we know they can't. With a nearly blue Mia and Sebastian, the moment lands brutally, insisting that love is no fairy tale in spite of the cinematic joys it brings.

Yet, Mia and Sebastian remain a fantastic couple, thanks largely to Gosling and Stone's genuine chemistry. With three films already under their belt, Gosling and Stone have cemented their status as Hollywood legends who are, hopefully, not done collaborating yet.