While most won’t immediately think of comedies when they hear the name Clint Eastwood, this Hollywood legend’s resume boasts several acclaimed funny films. From all-time great Westerns with directors like Sergio Leone, Best Picture-winning films of his own, and enjoyable franchises such as Dirty Harry, it’s a testament to the sheer variety of Eastwood’s output that he’s also appeared in several comedies of varied descriptions. With roles including a singing cowboy and an orangutan-partnered crooked, Eastwood’s comedy career featured wacky adventures, heartwarming character studies, and some underwhelming box office flops.

Although some of Eastwood’s worst movies were comedies, there were also several career highs and creative successes among a few clunkers and commercial failures. While Eastwood’s tough-guy reputation from roles such as The Man with No Name had a gritty edge to them, even those serious parts included some witty one-liners and clever quips. As a defining figure of 20th-century cinema and beyond, it’s important to look back on Eastwood’s often underappreciated comedy career.

11

Pink Cadillac (1989)

Clint Eastwood as Tommy Nowak

While Eastwood’s collaborations with directors such as Don Siegel and Sergio Leone were some of Hollywood’s most acclaimed creative partnerships, the same cannot be said for his work with Buddy Van Horn. As the director of three films, all starring Eastwood, Van Horn’s resume was less than impressive as he started with the orangutan-led sequel Any Which Way You Can, then made the worst Dirty Harry movie, The ᴅᴇᴀᴅ Pool, before topping things off with Eastwood’s most egregious comedy, Pink Cadillac.

Sadly, Pink Cadillac ended the pair’s collaboration on a sour note, as this poor action comedy left a lot to be desired. Telling the story of a bounty hunter and a group of white supremists chasing a woman who ran off in her husband’s prized pink Cadillac, there are few reasons to watch this charmless film. However, one interesting addition was a pre-fame Jim Carrey, who can be spotted in a minor role as a lounge entertainer.

10

Francis in the Navy (1955)

Clint Eastwood as Jonesy

Clint Eastwood gained his first credited film role with a minor part of Jonesy in Francis in the Navy. This black-and-white comedy starred Donald O’Connor in a dual role and told the story of a young lieutenant and his dream of joining the Navy. This forgettable, lighthearted comedy feels incredibly tame by today’s standards, and the most significant thing about it was that it kick-started Eastwood’s career in the movies.

Francis in the Navy featured classic misunderstandings, some light romance, and even a talking horse by the name of Francis. It was some inoffensive, harmless fun that has little to offer modern movie audiences and was an endearing example of just how much comedy movies have evolved over the seven decades. While lovers of old comedies may find something enjoyable in Francis in the Navy, it’s not exactly a must-watch film when it comes to Eastwood’s filmography.

9

Any Which Way You Can (1980)

Clint Eastwood as Philo Beddoe

Those surprised to learn that Clint Eastwood starred in a movie opposite an orangutan will be absolutely shocked to find out he also made a sequel. Any Which Way You Can was the follow-up to Every Which Way But Loose, Eastwood’s first adventure with his orange, primate companion Clyde, who got even more screen time here than in the previous film. Through a series of misadventures involving run-ins with the mob, cops, and motorcycle gangs, this truly is one of the most bizarre releases in Eastwood’s entire filmography.

With a meager 20% rating on Rotten Tomatoes, Any Which Way You Can was Eastwood’s lowest-rated film on the website. However, despite an illogical plot and poor reviews from critics, like the first film, Any Which Way You Can was a box office hit that grossed $70 million against its $15 million budget (via Box Office Mojo.) While cinephiles may consider this a low point in Eastwood’s career, the numbers don’t lie.

8

The Rookie (1990)

Clint Eastwood as Sergeant Nick Pulovski

The Rookie was an overbudgeted and disappointing action comedy directed by and starring Clint Eastwood. As a buddy cop story that paired Eastwood with a young detective played by Charlie Sheen, despite having plenty of potential, it was sad to see the way this production wasted the power of its talented cast and crew. With little chemistry between Eastwood and Sheen, the pair fumble through an uninspired script as they try to take down a German crime lord in downtown Los Angeles through an investigation into an exotic car theft ring.

The success of Die Hard two years before meant that plenty of action movies tried to walk the fine line between quippy comedy and thrilling narratives, and The Rookie was a prime example of this style being imitated poorly. As a box office bomb, viewers did not turn out to see this by-the-numbers buddy cop story, and the movie was overshadowed by the continued success of Home Alone, which was released just a few weeks prior.

7

City Heat (1984)

Clint Eastwood as Lieutenant Speer

While you’d think that viewers would have turned out in droves to see Clint Eastwood and Burt Reynolds share the big screen together in a buddy-crime-comedy, the results were a lackluster release with zero cultural relevance. City Heat starred the pair as two law enforcers investigating a murder in 1933 Kansas City. Although City Heat had a few funny moments, it’s hard to argue with famed film critic Roger Ebert’s ᴀssertion that it was “a complete, shocking mess” as he pondered “How do travesties like this get made?”

As a poor addition to the legacies of both Eastwood and Reynolds, most film fans have quietly agreed to forget that disappointing comedy was ever made. Reynolds himself said he knew during the filming that the movie was going to fail and expressed regret that “Warner Bros. will never let Clint and I act together again” (via Los Angeles Times.) It’s unfortunate that Reynolds’ ᴀssertion came true because, given the right material, these two could have made a fantastic comedic duo.

6

Paint Your Wagon (1969)

Clint Eastwood as Sylvester Newel/”Pardner”

As Clint Eastwood’s first and only foray into the world of movie musicals, it’s not difficult to understand why the actor notoriously hated Paint Your Wagon. Despite starring opposite the Hollywood legend Lee Marvin, this story about two prospector partners in a gold mining town who share the same wife never quite reached the heights needed to become a success. Released just as the musical had gone out of fashion, at 154 minutes in length, this was an exhausting and overlong musical comedy that was particularly funny.

With a slow-moving narrative that never quite gets off the ground, perhaps the best thing to come out of Paint Your Wagon was that it was later hilariously parodied in an episode of The Simpsons. Eastwood was truly a Western movie legend, but when the tough-guy persona of The Man with No Name was traded for a film about singing cowboys, he was less than intimidating. While Paint Your Wagon was not a terrible movie, it feels totally outdated today.

5

Every Which Way but Loose (1978)

Clint Eastwood as Philo Beddoe

Clint Eastwood shocked film fans worldwide in 1978 when he starred in an offbeat comedy that you’d be forgiven for thinking you imagined in some strange fever dream. But no, Every Which Way But Loose, the movie starring Eastwood opposite an orangutan named Clyde, was in fact a real movie. Not only this, but it was a hit at the box office, and viewers turned out in droves to watch once gruff and intimidating The Man with No Name provide a few laughs in an uncharacteristically light adventure.

As the release that remains Eastwood’s biggest film to this day, Every Which Way but Loose was a PG farce that the entire family could enjoy. There was something endearing about a man and his monkey traversing the American West in search of his lost love, all while being pursued by police and a motorcycle gang out for revenge. Every Which Way but Loose may not have been the most thought-provoking film in Eastwood’s back catalog, but if you can turn your brain off for a bit, it works perfectly as a mindless, lighthearted entertainment.

4

Kelly’s Heroes (1970)

Clint Eastwood as Kelly

Clint Eastwood was the leader of a crew of American GIs trying to rob a French bank of their Nazi gold in Kelly’s Heroes. As an enjoyable World War II heist film, this genre-bending story was also a pointed satire on the nature of modern military efforts and cleverly blended aspects of heist capers with a true battlefield war movie. While some of the humor may feel dated today, looking back on Kelly’s Heroes, it’s clear this was a well-executed, lighthearted adventure that showcased Eastwood’s often undervalued comedic skills.

Featuring Eastwood alongside notable names like Don Rickles and Donald Sutherland, Kelly’s Heroes took inspiration from real-life train robberies and was even featured as one of Channel 4’s 100 Greatest War Films of All Time. With plenty of energy and a well-constructed narrative, those who doubt Eastwood’s comedy credentials need to check out Kelly’s Heroes.

3

Honkytonk Man (1982)

Clint Eastwood as Red Stovall

Honkytonk Man was one of Clint Eastwood’s most low-key and quietly affecting movies, as it balanced upbeat comedy with poignant sentimentality. With a screenplay by Clancy Carlile, who adapted his own novel, Honkytonk Man starred Eastwood as a traveling tuberculosis-suffering western singer, Red Stovall, who has been given the chance to make it big at the Grand Ole Opry in Nashville, Tennessee. Accompanied by his teenage nephew Whit Wagoneer, the pair go on a series of misadventures as they make their way to Red’s big audition.

As one of the more personal efforts in Eastwood’s body of work, Honkytonk Man was equal parts funny and endearing as Red and Whit bonded through shared experiences. A true hidden gem of the 1980s, Honkyton Man wasn’t a hit at the box office and represented Eastwood’s lowest-grossing film for over a decade. Despite this, everything about Honkytonk Man worked, and those who have seen it will recognize it as an accomplished, feel-good comedy.

2

Bronco Billy (1980)

Clint Eastwood as Billy “Bronco Billy” McCoy

Clint Eastwood played a modern-day cowboy trying to keep his struggling traditional Wild West show alive in Bronco Billy. With a mix of action, comedy, and drama, it’s clear that this was one of Eastwood’s most personal films as a star and a director, as he surely connected deeply with Bronco’s struggles, having also spent a career in the realm of the Wild West. While there were plenty of laughs in Bronco Billy, there were also serious undertones as he struggled to pay his crew and keep the show going.

With a sense of warmth, humor, and nostalgia, Bronco Billy harkened back to an earlier era as it celebrated American innocence and was unashamedly sentimental. While the film wasn’t a major box office success, it showed off Eastwood’s comedic talents and proved that he was a much funnier actor in more grounded material with an emotional core, rather than in the wacky antics of his worst comedies.

1

Thunderbolt and Lightfoot (1974)

Clint Eastwood as John “Thunderbolt” Doherty

Before taking Hollywood by storm with his Best Picture-winning Vietnam War movie The Deer Hunter, Michael Cimino honed his skills with Clint Eastwood in the fantastic crime comedy Thunderbolt and Lightfoot. While Eastwood’s track record for funny films isn’t the greatest, this story about a disguised preacher being unintentionally rescued from ᴀssᴀssination by a car thief showcased his comedy skills at their peak. Starring Eastwood opposite Jeff Bridges, these two made for a compelling pair, and Bridges even received an Academy Award nomination for his performance.

As a story of heists, shootouts, and robberies, Thunderbolt and Lightfoot was as action-packed as it was hilarious. Watching as Eastwood’s seemingly goody-goody character unwittingly ᴀssisted in a series of robberies, it was later revealed that he was actually a notorious bank robber being hunted by his former gang. With strong direction, great performance, and a hilarious script, Clint Eastwood gave his greatest comedy performance in Thunderbolt and Lightfoot.

Sources: Rotten Tomatoes, Box Office Mojo, Roger Ebert, Los Angeles Times, 100 Greatest War Films of All Time