Jack Lemmon stands as one of Hollywood’s most versatile actors, seamlessly shifting between comedy and drama with remarkable ease. His expressive face, impeccable timing, and emotional depth allowed him to create characters that still resonate with audiences today. From neurotic businessmen to recovering alcoholics, Lemmon’s performances showcase a rare talent that earned him two Academy Awards and a permanent place in film history.
1. It Should Happen to You (1954)
Fresh-faced and earnest, Lemmon made his film debut opposite Judy Holliday in this charming comedy. Playing Pete Sheppard, a documentary filmmaker who falls for a fame-obsessed woman, he immediately showcased his trademark nervous energy and likable everyman quality.
The chemistry between Lemmon and Holliday sparkles with authenticity. His performance balances frustration and affection perfectly, establishing the foundation for his future romantic comedies. Director George Cukor recognized Lemmon’s potential early, allowing his natural comedic timing to shine through. This breakthrough role announced the arrival of a major talent who would dominate Hollywood for decades.
2. Mister Roberts (1955)
Naval comedy brought Lemmon his first Oscar as Ensign Pulver, a lazy but lovable officer aboard a cargo ship during World War II. His character’s transformation from shirker to responsible leader showcases Lemmon’s ability to evolve a character believably.
The role required perfect comic timing, especially in scenes involving Pulver’s elaborate pranks against the tyrannical captain. Lemmon’s performance stands out even alongside heavyweights Henry Fonda and James Cagney. Critics particularly praised how he balanced broad comedy with subtle emotional notes. This early career triumph established Lemmon as a performer who could steal scenes while serving the story.
3. Some Like It Hot (1959)
Comedic genius radiates from Lemmon’s performance as Jerry/Daphne, a musician forced to disguise himself as a woman to escape gangsters. His physical comedy reaches masterful heights as he navigates high heels, makeup, and unwanted romantic advances. The famous tango scene with Joe E. Brown demonstrates Lemmon’s fearless commitment to a role.
Director Billy Wilder later claimed Lemmon was the only actor who could have pulled off the character’s complex emotional journey. Beyond the laughs, Lemmon infuses Jerry with surprising depth. The gradual identity confusion as Daphne embraces her female persona creates one of cinema’s most nuanced comic performances in what many consider the greatest comedy ever made.
4. The Apartment (1960)
Corporate climber C.C. Baxter lends his apartment to company executives for their extramarital affairs in this Billy Wilder masterpiece. Lemmon portrays Baxter’s moral awakening with remarkable subtlety, creating a character caught between ambition and decency. The performance earned Lemmon his first Best Actor Oscar nomination.
His ability to convey loneliness while straining spaghetti through a tennis racket demonstrates his gift for making ordinary moments extraordinary. Lemmon’s chemistry with Shirley MacLaine feels genuinely tender amid the film’s cynical world. His transformation from eager-to-please company man to someone who stands up for love and dignity remains one of cinema’s most satisfying character arcs.
5. The Notorious Landlady (1962)
American diplomat William Gridley doesn’t believe his beautiful landlady (Kim Novak) murdered her husband in this underrated comedy-mystery. Lemmon brings his characteristic nervous energy to the role, creating a character whose attraction to danger feels both foolish and endearing.
The film showcases Lemmon’s physical comedy skills, particularly in scenes where he attempts to investigate the supposed crime. His reactions—from startled jumps to suspicious glances—generate consistent laughs. Director Richard Quine gives Lemmon room to display his range, from romantic moments to screwball comedy sequences. Though not among his most celebrated films, Lemmon’s performance demonstrates how he could elevate standard material through sheer charisma and commitment.
6. Days of Wine and Roses (1962)
Alcoholism’s devastating impact takes center stage in this harrowing drama where Lemmon plays Joe Clay, a PR man whose drinking destroys his life. His portrayal of addiction feels painfully authentic, from euphoric binges to desperate withdrawals.
The famous greenhouse destruction scene remains one of cinema’s most powerful depictions of addiction’s grip. Lemmon’s performance—sweating, shaking, and pleading—shows his willingness to abandon vanity for truth. Director Blake Edwards, known primarily for comedies, trusted Lemmon to carry this dark material. The performance marked a turning point in Lemmon’s career, proving he could handle serious dramatic roles with the same excellence he brought to comedy, earning him another Oscar nomination.
7. Irma la Douce (1963)
Reuniting with Billy Wilder, Lemmon portrays Nestor Patou, an honest policeman who falls for Parisian prostitute Irma (Shirley MacLaine). His character creates an alter ego—”Lord X”—to become her exclusive client, leading to increasingly complicated scenarios. Lemmon delivers both physical comedy (struggling with Lord X’s disguise) and emotional depth (genuine love for Irma).
His ability to play essentially two characters—the straightlaced Nestor and aristocratic Lord X—showcases his remarkable versatility. The performance earned praise for avoiding slapstick stereotypes while maintaining comic energy. Lemmon manages to make Nestor’s absurd plan seem almost reasonable through his earnest portrayal, creating sympathy for a character whose actions might otherwise seem creepy.
8. How to Murder Your Wife (1965)
Slapstick meets marital mayhem in this delightfully absurd comedy where Lemmon portrays Stanley Ford, a comic strip artist who drunkenly marries a beautiful Italian woman (Virna Lisi) and then plots her fictional murder in his comic strip. The genius of Lemmon’s performance lies in his physical comedy and facial expressions that communicate volumes without words. Stanley’s mounting frustration and panic become increasingly hilarious as his fictional murder plot gets mistaken for a real conspiracy. Lemmon balances the character’s exasperation with an underlying charm that keeps the audience rooting for him despite his outlandish schemes.
Fun fact: Lemmon actually learned to speak some Italian for the role, adding authenticity to his interactions with Lisi’s character!
9. The Great Race (1965)
Villainous Professor Fate brought out Lemmon’s rarely-seen over-the-top comedic side in this slapstick adventure. Sporting a handlebar mustache and perpetual scowl, he created an unforgettable antagonist determined to win an auto race from New York to Paris. Lemmon throws himself into physical comedy with reckless abandon.
Covered in cake during the film’s epic pie fight or trapped in an ice cave, his commitment to the character’s cartoonish villainy never wavers. The dual role as Prince Hapnik showcases Lemmon’s range within a single film. Though critics were mixed on the movie itself, Lemmon’s performance received universal praise for bringing Wile E. Coyote-like determination to a live-action character, creating a worthy adversary for Tony Curtis’s perfect hero.
10. The Fortune Cookie (1966)
Ambulance-chasing lawyer “Whiplash Willie” Gingrich represents the darker side of Lemmon’s acting range. His portrayal of a man willing to orchestrate an insurance fraud scheme involving his brother-in-law (Walter Matthau) balances sleaze with unexpected charm. Lemmon perfectly captures the moral conflict of someone who knows better but can’t help himself. His facial expressions as his conscience battles his greed provide a masterclass in subtle acting.
This first pairing with Matthau launched one of Hollywood’s greatest partnerships. Though Matthau won the Oscar for his supporting role, Lemmon’s performance as the reluctant fraud participant provides the emotional core that makes the story work, showing his ability to create sympathy for deeply flawed characters.
11. The Odd Couple (1968)
Neurotic neat-freak Felix Ungar became one of Lemmon’s signature roles in this perfect comedy about mismatched roommates. His portrayal of a recently separated man obsessed with cleanliness, cooking, and clearing his sinuses created an iconic character instantly recognized in popular culture.
Lemmon finds humanity in what could have been a one-dimensional character. His physical mannerisms—from his posture to his precise movements—tell us everything about Felix without a word of dialogue. The chemistry with Walter Matthau’s Oscar Madison elevated both performances. Lemmon makes Felix’s transformation from suicidal wreck to confident man genuinely moving while never sacrificing the laughs. This performance cemented Lemmon as an actor who could make fussy, difficult characters endearing.
12. The Out-of-Towners (1970)
Middle-American George Kellerman faces a nightmare trip to New York City in this Neil Simon comedy. Lemmon portrays a man whose optimism gradually crumbles as everything goes wrong—missed connections, stolen luggage, muggings, and a city-wide strike. The performance showcases Lemmon’s gift for controlled escalation. His character’s frustration builds naturally from mild annoyance to full-blown panic without ever feeling forced or repetitive. Lemmon makes George’s increasing hysteria both funny and relatable.
His chemistry with Sandy Dennis as his equally suffering wife grounds the increasingly absurd situations in emotional reality. The performance demonstrates Lemmon’s ability to maintain audience sympathy while his character becomes increasingly unhinged.
13. The Front Page (1974)
Newspaper editor Walter Burns will do anything to keep his star reporter from quitting in this remake of the classic comedy. Lemmon brings manic energy to Hildy Johnson, a role traditionally played as the straight man to Burns’ schemer. His verbal sparring with Walter Matthau creates some of cinema’s fastest, wittiest dialogue exchanges. Director Billy Wilder allowed the pair to develop their natural rhythm, resulting in performances that feel spontaneous despite the precisely timed comedy.
Lemmon manages to make Hildy both cynical and idealistic—a hardened newsman who still believes in journalistic integrity. Though not as celebrated as their other collaborations, the film demonstrates Lemmon’s ability to adapt classic material while maintaining his distinctive personality.
14. Save the Tiger (1973)
Garment manufacturer Harry Stoner’s moral crisis earned Lemmon his second Oscar, this time for Best Actor. His portrayal of a once-idealistic businessman contemplating arson fraud captures the disillusionment of post-Vietnam America with haunting precision. Lemmon delivers some of cinema’s most powerful monologues as Harry reminisces about his World War II experiences and simpler times.
His performance shifts between outer confidence and inner despair, often within the same scene. Director John G. Avildsen praised Lemmon’s willingness to appear unsympathetic. The performance resonated with audiences experiencing similar ethical compromises during difficult economic times. Lemmon makes Harry’s corruption understandable without excusing it, creating one of film’s most complex portraits of the American Dream gone sour.
15. Tribute (1980)
Broadway adaptation Tribute showcases Lemmon as Scottie Templeton, a terminally ill former Broadway agent attempting to reconnect with his estranged son. His performance balances the character’s showbiz flamboyance with genuine emotional vulnerability. Lemmon’s portrayal of a man facing mortality while hiding behind jokes earned him another Oscar nomination.
The scene where Scottie finally breaks down demonstrates Lemmon’s ability to transition from comedy to raw emotion seamlessly. Critics noted how Lemmon avoided sentimentality despite the material’s potential for manipulation. His Scottie feels like a real person rather than a collection of deathbed clichés. The performance resonates particularly when viewed alongside Lemmon’s earlier work, showing how he matured as an actor while maintaining his essential humanity.
16. Missing (1982)
Political thriller Missing features Lemmon as Ed Horman, a conservative American father searching for his missing son in Chile after Pinochet’s coup. His transformation from government-trusting patriot to disillusioned truth-seeker creates the film’s emotional backbone. Lemmon’s restrained performance avoids melodrama despite the harrowing subject matter. His scenes investigating his son’s disappearance while butting heads with embassy officials showcase subtle character development through small gestures and expressions.
Director Costa-Gavras praised Lemmon’s courage in taking such a politically charged role. The performance earned Lemmon another Oscar nomination and demonstrated his willingness to use his star power for meaningful stories. His portrayal of parental determination transcends political viewpoints, making the film’s message accessible to all audiences.
17. The China Syndrome (1979)
Nuclear power plant supervisor Jack Godell discovers dangerous corner-cutting at his facility in this prescient thriller. Lemmon portrays a man torn between company loyalty and public safety with increasing intensity as the story progresses. The performance builds masterfully from professional confidence to paranoid terror. Godell’s technical explanations become more frantic as he realizes the potential for catastrophe, culminating in the character’s breakdown on live television.
Released just 12 days before the Three Mile Island accident, the film gained eerie relevance. Lemmon’s authentic portrayal of a whistleblower facing corporate intimidation earned him yet another Oscar nomination. His ability to make complex technical concepts emotionally compelling helps the film maintain its power decades later.
18. Glengarry Glen Ross (1992)
Aging real estate salesman Shelley Levene desperately clings to his fading career in this adaptation of David Mamet’s Pulitzer Prize-winning play. Lemmon’s portrayal of “The Machine” turned pathetic has-been ranks among cinema’s most heartbreaking character studies. His opening scene—begging his manager for better leads—showcases vulnerability rarely seen in male characters. Lemmon makes Shelley’s desperation palpable without asking for sympathy, creating discomfort through authenticity rather than manipulation.
The performance stands out even in an all-star cast including Al Pacino and Alec Baldwin. Lemmon’s portrayal of professional obsolescence resonated with audiences facing similar economic insecurity. His final scene, where Shelley confesses to a crime, demonstrates how completely Lemmon could inhabit a character’s psychological collapse.
19. Grumpy Old Men (1993)
Neighborhood rivals John Gustafson and Max Goldman (Walter Matthau) battle over fishing spots and a new woman in town in this late-career comedy hit. Lemmon brings surprising depth to what could have been a one-note character, creating a widower whose grumpiness masks loneliness. The performance showcases Lemmon’s physical comedy skills even in his 70s. His ice-fishing scenes and pranks against Matthau demonstrate timing honed over decades.
Reuniting with Matthau revitalized both actors’ careers. Their genuine friendship infuses the fictional rivalry with authentic history. Lemmon balances the film’s broader comedy moments with touching scenes involving his character’s relationship with his daughter. The performance proves Lemmon’s appeal remained undiminished by age.
20. My Fellow Americans (1996)
Former presidents from opposing parties find themselves on the run together in this political comedy. Lemmon plays Democratic ex-President Russell Kramer opposite Republican James Garner, creating chemistry that elevates the sometimes-silly plot. The role allowed Lemmon to poke fun at political pretensions while maintaining his trademark humanity.
His character’s gradual friendship with his former rival feels genuine despite the film’s outlandish scenarios. One of Lemmon’s final leading roles showcases his enduring screen presence and comic timing. Though not critically acclaimed, the film demonstrates how Lemmon could find truth in commercial material. His portrayal of a politician rediscovering his principles provides a fitting capstone to a career built on characters struggling with their moral compass.
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