Jack Lemmon's 10 Best Movies, Ranked

April 18, 2024, 3:05 p.m.

Movies

Jack Lemmon's 10 Best Movies, Ranked

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Summary Jack Lemmon's commitment to vulnerable everyman characters made him one of the greatest actors of his generation.

His performances in iconic movies like Glengarry Glen Ross showcased his range and skill as an actor.

Lemmon's comedic chemistry with Walter Matthau in films like Grumpy Old Men proved his enduring comedic talent.

As acclaimed in comedy as he was in drama, Jack Lemmon was truly one of the greatest actors of the 20th century who imbued every role he played with a powerful sense of humanity. As a two-time Academy Award winner, and the first actor to win both Best Actor and Best Supporting Actor, Lemmon made Hollywood history over the course his more than 50-year career. Strongly associated with playing vulnerable everyman characters, Lemmon showcased a determinated commitment to every role he played in more than 60 movies.

With a long-standing comedic partnership with Walter Mattheau, iconic collaobortions with director Billy Wilder, and acclaimed performances in intense drama films, Lemmon starred in some of the greatest movies ever made. From Some Like It Hot to Glengarry Glen Ross, Lemmon’s range and skill cemented his reputation as one of the finest performers of his generation. While the genre and styles of his movies varied over the years, the best Lemmon movies were always solidly entertaining films backed up with an extraordinary performance.

10 JFK (1991)

Jack Lemmon as Jack Martin

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buy Not available Not available Not available Director Oliver Stone Release Date December 20, 1991 Cast Sally Kirkland , Anthony Ramirez , Ray LePere , Steve Reed , Jodie Farber , Columbia Dubose Runtime 189 minutes

After an already extraordinary career of more than 40 years in show business, Jack Lemmon gave one of his most memorable late-career performances with a brief appearance as Jack Martin in Oliver Stone’s JFK. With a star-studded cast that also included Lemmon’s frequent co-star Walter Matthau, Lemmon as Martin, the man who helped kick off Jim Garrison’s investigation into the assassination of John F. Kennedy. With a truly impressive ensemble cast, Lemmon added to the extraordinary appeal of this paranoia-laced political thriller.

Despite the controversial nature of JFK, which fully embraced conspiracy theories about the truth behind the assassination of Kennedy, the movie was a tense and effective political thriller that Stone described as a “counter myth” (via Rolling Stone) to explain the death of the 35th United States president. While many of its claims should be taken with a pinch of salt, this did not take away from the impressive achievement that was JFK. The first of three movies Stone made about presidents, he later followed JFK with Nixon and W.

9 Missing (1982)

Jack Lemmon as Ed Horman

Full of political intrigue and a mysterious missing person, Missing starred Jack Lemmon as Ed Horman in a movie inspired by a true story set against the backdrop of the United States-backed Chilean coup of 1973. Lemmon played a father who arrived in Chile in search of his son, an American journalist, who disappeared during a military coup. As Ed desperately searched for his son the conspiracy surrounding him grew ever larger as it appeared everyone, including the Government, was keeping dark and untold secrets from him.

Lemmon expertly played a loving father who was in over his head trying to get answers as the stark realities of his son’s disappearance slowly crept to the surface. With a strong supporting cast that included Sissy Spacek, as Ed’s strong-willed daughter-in-law, Missing was a tense and effective drama that too aim directly at the American government and their deposition of democratically elected political figures. A smart and intelligent biographical thriller, Missing showcased that Lemmon was just as effective an actor in dramas as he was in comedy.

8 Save The Tiger (1973)

Jack Lemmon as Harry Stoner

Jack Lemmon received the Acamedy Award for Best Actor for his role as the disillusioned war veteran Harry Stone in Save the Tiger, a tense drama that explored moral conflict in contemporary America. Lemmon gave an extraordinary performance as a businessman who found extreme anxiety pervading every aspect of his life while he struggled to keep his company afloat and was consistently left disappointed by the moral failings of those around him. Forced to make difficult decisions, Save the Tiger highlighted the most depressing aspects of the American Dream and those it so often left behind.

While Save the Tiger was not as acclaimed as Lemmon’s most famous roles, it was a real acting highlight in his long and varied career that signaled him as one of the greatest actors of his generation. While Save the Tiger was a slow burn that had featured lengthy scenes and overlong dialogue, the commitment that Lemmon gave to the part proved that nobody could portray anxiety on screen like him. Save the Tiger was a forgotten gem from the New Hollywood era, when movies first started to take unflinching looks at society and did not like what they revealed.

7 Grumpy Old Men (1993)

Jack Lemmon as John Gustafson Jr

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buy Not available Not available Not available Director Donald Petrie Release Date December 25, 1993 Cast Jack Lemmon , Walter Matthau , Ann-Margret , Kevin Pollak , Daryl Hannah , Ossie Davis

Jack Lemmon proved he had not lost his comedic touch with the release of Grumpy Old Men, a romantic comedy that paired him once again with his most frequent co-star Walter Matthau. Grumpy Old Men was a light-hearted film about two neighbors with a long-standing rivalry that only intensified when a new female neighbor moved in across the street. Although Lemmon and Matthau had funnier collaborations in the past, it was a real treat to see these two legends sharing the screen once again.

Grumpy Old Men proved that Lemmon and Matthau had not lost any of their innate comedic chemistry as they expertly played off one another with hilarious consequences. With Lemmon in his late 60s, Grumpy Old Men was an age-appropriate role that leaned into the acclaimed legacy of its two stars and featured a strong supporting performance from Ann-Margaret. A less acclaimed sequel called Grumpier Old Men was released two years later, although this proved the joke really only worked once.

6 Mister Roberts (1955)

Jack Lemmon as Ensign Frank Thurlowe Pulver

Mister Roberts brought Jack Lemmon his first Oscar for Best Supporting Actor as his incredible comedic powers were on full display through the role of the laundry and morale officer Ensign Frank Thurlowe Pulver. The star-studded cast also featured Henry Fonda, James Cagney, and William Powell as Navy officers in the waning days of World War II who were frustrated by the petty denials of their captain. With plenty of laugh-out-loud moments and at-sea antics, Mister Roberts was a classic comedy that exploited its incredible comedic talent.

Despite the troubled production history of Mister Roberts, as the original director, John Ford, was replaced by Mervyn LeRoy due to behind-the-scenes conflicts with Fonda and Cagney (via Far Out), the movie was a hit with audiences and critics. Lemmon’s character was so popular he even led the sequel Ensign Pulver in 1964, although Lemmon did not return and was replaced by Robert Walker in the title role. An underappreciated comedy, those with a love for Lemmon’s unmatched comedic skill should check out Mister Roberts.

5 The Odd Couple (1968)

Jack Lemmon as Felix Ungar

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buy Not available Not available Not available Director Gene Saks Release Date May 16, 1968 Cast Jack Lemmon , Walter Matthau , John Fiedler , Herb Edelman , David Sheiner , Larry Haines Runtime 105 minutes

The greatest pairing of Jack Lemmon and Walter Matthau was The Odd Couple, a funny, moving, and at times deeply sad comedy about friendship and all the hardships that came with it. Lemmon played Felix Ungar, a down-on-his-luck divorcee who contemplated ending it all after his wife left him, and Matthau was Oscar Madison, the messy friend who invited him to move in with him while he got back on his feet. What started as a caring helping hand soon turned to conflict as the pair discovered just how different they were from one another.

Lemmon gave a powerful and hilarious performance as Felix that simultaneously conveyed all his particular eccentricities while also hinting at the deep sadness hidden underneath his character. The Odd Couple could have been a complete farce but it maintained a sense of vulnerability that was sprinkled throughout its quick-witted dialogue and sharp comebacks. As one of the best comedies of the 1960s, the same can definitely not be said about its lackluster sequel The Odd Couple II from 1998.

4 Days Of Wine And Roses (1962)

Jack Lemmon as Joe Clay

While at first Days of Wine and Roses looked like it had all the makings of a classic romance picture, the story soon devolves into a tragic tale of alcoholism, dependency, and the painful way that addiction brought down everybody around it. Jack Lemmon delivered an extraordinary performance as Joe Clay who, after finding the love of his life, systematically brought her down to share his passion for drinking with him. A grim depiction of the way that alcohol disuse puts people on a path toward destruction, Days of Wine and Roses was a heart-breakingly sad movie by director Blake Edwards.

Full of shame-inducing scenes Lemmon gave one of his best performances as Clay that was equally matched in passion and vulnerability by Lee Remick as his love-interest and later wife Kirsten Arnesen-Clay. At the time of its release, Days of Wine and Roses was Lemmon’s most dramatic role as it outline the difficulties of romantic love superseding an unhealthy love for alcohol. Days of Wine and Roses became even more tragically sad as when Clay tried to clean-up his act, he was forced to witness his wife falling further into the pit of addiction that he had thrown her into.

3 Glengarry Glen Ross (1992)

Jack Lemmon as Sheldon Levene

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buy Not available Not available Not available In a high-pressure real estate office, desperation drives a group of salesmen to extreme measures to secure their jobs. As they navigate deceit, betrayal, and cutthroat competition, each character's moral compass is tested. With tensions escalating and stakes at an all-time high, the salesmen grapple with the consequences of their actions. Amidst a backdrop of intrigue and manipulation, the story unfolds over two intense days, culminating in surprising revelations and poignant moments of reflection. Director James Foley Release Date October 2, 1992 Cast Al Pacino , Jack Lemmon , Alec Baldwin , Ed Harris , Alan Arkin , Kevin Spacey , Jonathan Pryce Runtime 100 Minutes

The crowning achievement of the latter part of Jack Lemmon’s career came with his extraoridinary performance as Sheldon Levene in Glengarry Glen Ross. Although Glengarry Glen Ross was best remembered for Alec Baldwin’s powerful “always be closing” scene, the film was so much more than this as Lemmon brought nuance and vulnerability to this adaptation of Pultizer Prize-winning play by David Mamet. Dubbed ‘Shelley the Machine’, Lemmon played a once-successful real estate salesman whose job was in danger if he could not prove his worth by becoming one of the top deal closers of the month.

Set over the course of two days, Sheldon had a sick daughter in hospital and the pervading sense of anxiety for his soon to be crumbling existence was felt throughout Glengarry Glen Ross. Lemmon’s performance was truly a standout aspect of Glengarry Glen Ross, which was even more impressive considering the cast consisted of the likes of Al Pacino, Alan Arkin, and Ed Harris. While Glengarry Glen Ross bombed at the box office, it received universal critical acclaim and has since gained a reputation as a cult classic.

2 Some Like It Hot (1959)

Jack Lemmon as Jerry / Jerraldine

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buy Not available Not available Not available Some Like It Hot is a comedy crime film starring Marilyn Monroe, Tony Curtis, and Jack Lemmon. Directed by Billy Wilder, Some Like it Hot is set in Prohibition-era Chicago and centers on two musicians named Joe and Jerry who go on the run and disguise themselves as women after witnessing a mob hit. Director Billy Wilder Release Date March 15, 1959 Cast Marilyn Monroe , Tony Curtis , Jack Lemmon , George Raft , Pat O'Brien , Joe E. Brown Runtime 121 Minutes

The greatest of all Jack Lemmon’s out-and-out comedies has to be Some Like It Hot, the farcical gender-bending crime comedy that he co-starred in with Tony Curtis and Marilyn Monroe. As funny today as when it was first release, Lemmon’s pure commitment to his role as on full display as himself and Curtis played two men who disguised themselves as musicians to escape mafia gangsters. With an outrageous plot, Some Like It Hot could have fallen flat on its feet his not for convincing trio that was Lemmon, Curtis, and Monroe, who all delivered career-defining performances.

Produced without the approval of the Motion Picture Production Code, Some Like It Hot pushed the boundaries of what could be depicted onscreen was a prime example of the destamantling of social taboos within media during the 1960s. Some Like It Hot was clever, racy, and at times deeply insightful, and acted as the first of four collaborations between Lemmon and director Billy Wilder. An almost perfect comedy, Some Like It Hot was as trailblazing as it was hilarious.

1 The Apartment (1960)

Jack Lemmon as C.C. "Bud" Baxter

As the Best Picture winner of 1960, The Apartment was director Billy Wilder and its star Jack Lemmon firing on all cylanders and delivering what would the best work in both of their acclaimed careers. A Christmas comedy-drama, The Apartment featured Lemmon as a timid office employee at an insurance company in New York City who ended up lending out his sought-after city apartment to his superiors to meet with their mistresses. As Bud Baxter, Lemmon was devastated to learn that the elevator operator that he longed after was having an affair with his boss in his own home.

While The Apartment was full of hilarious moments, it was also deeply tragic as Baxter was walked on by his superiors and the elevator operator, played by Shirley MacLaine, was strung along to the point that she tried to end her life. At it’s core, The Apartment was the story of a man who learned how to stop letting people push him around and stand up for himself. As the greatest performance in Lemmon’s entire filmography, the fact that he did not win his Best Picture nomination was one of the biggest travestries in Oscar history.

Sources: Rolling Stone, Far Out