Humphrey Bogart
When you put two of Hollywood's toughest tough guys in the same room, sparks are bound to fly. Robinson and Humphrey Bogart made five films together, but their final collaboration, 'Key Largo' (1948), is the main event. Robinson had previously always
received top billing over Bogart, but by 1948, the tables had turned. In the film, Robinson plays the vicious gangster Johnny Rocco, holding a hotel full of people, including Bogart's cynical war veteran Frank McCloud, hostage during a hurricane. The tension between the two is palpable; Rocco is a monster of pure ego, and McCloud is the reluctant hero who finally stands up to him. Their face-off is a masterclass in screen acting.
Barbara Stanwyck
While they only shared a few minutes of screen time in the film noir classic 'Double Indemnity' (1944), their impact is undeniable. Robinson plays Barton Keyes, a brilliant and dogged insurance investigator who is the conscience of the film. Stanwyck is the venomous Phyllis Dietrichson, who plots murder with Fred MacMurray. Keyes is the only one smart enough to see through the scheme. Though they don't have many direct scenes, Keyes is constantly in pursuit of the truth about Phyllis, making their indirect dynamic the film's central conflict. They finally shared more substantial scenes in the 1955 Western 'The Violent Men', where Robinson plays a disabled cattle baron and Stanwyck is his scheming, cheating wife.
James Cagney
Amazingly, the two definitive gangsters of Warner Bros. in the 1930s only appeared in one film together: 'Smart Money' (1931). Filmed just as Robinson's 'Little Caesar' made him a star and before Cagney's 'The Public Enemy' was released, the movie is primarily a Robinson vehicle. He plays Nick 'The Barber' Venizelos, a small-town gambler who rises to become a big-city kingpin. Cagney plays his loyal right-hand man, Jack. While it's Robinson's show, watching these two dynamos share the screen, their crackling energy and rapid-fire dialogue bouncing off each other, is a treat for any classic film fan.
Joan Bennett
Robinson found one of his most frequent and effective screen partners in Joan Bennett. They teamed up for two of director Fritz Lang’s darkest film noirs: 'The Woman in the Window' (1944) and 'Scarlet Street' (1945). In both films, Robinson plays a lonely, middle-aged man who falls into a web of crime and obsession spun by Bennett's femme fatale. In 'The Woman in the Window', he's a professor whose infatuation leads to accidental murder; in 'Scarlet Street', he's a henpecked cashier and amateur painter destroyed by his love for her. Their chemistry is electric and tragic, a perfect pairing for Lang's fatalistic worldview.
Claire Trevor
In 'Key Largo', Claire Trevor delivered an Academy Award-winning performance as Gaye Dawn, the alcoholic, faded singer and girlfriend of Robinson's gangster Johnny Rocco. Her character provides the film with its most heartbreaking scene. Desperate for a drink, she is cruelly forced by Rocco to sing for his captive audience. Her raw, painful, a cappella rendition of 'Moanin' Low' is an all-time classic movie moment, reportedly filmed by director John Huston without rehearsal to capture a genuine, unpolished performance. The dynamic between Robinson's casual cruelty and Trevor's shattered dignity is utterly devastating and unforgettable.
George Raft
The on-screen tension between Robinson and George Raft in the 1941 drama 'Manpower' was fueled by real-life animosity. Raft resented being third-billed behind Robinson and co-star Marlene Dietrich and reportedly felt Robinson was miscast. This friction translated perfectly to the screen. They play rival high-voltage linemen and friends who compete for the affection of Dietrich's character. The film is a rough-and-tumble melodrama, and the genuine conflict between the two actors gives their characters' competition an extra layer of authenticity. Despite the off-screen drama, which reportedly halted production at times, the result is a compelling working-class love triangle.
Mary Astor
Long before she became the iconic femme fatale of 'The Maltese Falcon', Mary Astor co-starred with Robinson in the 1933 pre-Code comedy 'The Little Giant'. The film was one of Robinson's first efforts to parody his tough-guy image. He plays 'Bugs' Ahearn, a bootlegger who, with the end of Prohibition, decides to retire and break into high society. He falls for a down-on-her-luck socialite played by Astor, who represents the class and culture he desperately wants. Astor's refined grace is the perfect comic foil for Robinson's brash, uncultured but good-hearted ex-gangster, making for a charming and funny pairing.
