The Three Movies Clint Eastwood Considered The Biggest Risks Of His Career (Only One Was A Hit)

There are three movies that Clint Eastwood considers to be his biggest career risks, but only one paid off at the box office. Despite the stardom Eastwood achieved as the “Man with No Name” in Sergio Leone’s Dollars trilogy, it still took a few years for him to break through in America. The movie that truly cemented him was Dirty Harry, a controversial 1971 thriller that nonetheless was a gigantic success, and led to one of the few Clint Eastwood movie franchises.

Eastwood’s screen persona quickly became that of the stoic man of action who said little – but always had a dry quip ready when required. From the 1970s through to the 1990s, most of his biggest hits came in the thriller or action genres, from The Gauntlet right on down to In the Line of Fire. That’s not to say he didn’t take any chances as a performer though, and in between the diet of thrillers or Clint Eastwood Westerns, he rolled the dice on several projects.

Eastwood Considers The Beguiled, Honkytonk Man & Broncho Billy As His Biggest Risks

Clint also felt Unforgiven wouldn’t be commercial

During a 1996 conversation with Charlie Rose, Eastwood was asked which of his films he considered the biggest swings. In short succession, Clint cited The Beguiled, Honkytonk Man and Bronco Billy as his biggest gambles, largely because they “were away from character.” Indeed, none of the three Eastwood cited as risks are action movies or crime thrillers, with The Beguiled being a creepy, gothic thriller while both Bronco Billy and Honkytonk Man are moving character studies.

Bronco Billy is the sweetest of the bunch, with Eastwood’s title character leading a traveling Wild West show filled with misfits and dreamers. The film itself is a metaphor for the life of an actor, and it can’t be a mistake that the story feels like a commentary on the waning popularity of Westerns. Honkytonk Man is a musical drama set during the Great Depression, where Eastwood’s dying singer takes his nephew on a road trip while he tries to reach an important audition.

Honkytonk Man has a real warmth about it, especially as Clint Eastwood’s nephew is played by his son, Kyle.

The film features arguably the biggest loser role Eastwood has played and might be the furthest from his tough guy screen image it’s possible to get. It’s also one of the star’s darker dramas and features a rare instance of one of his characters dying. Still, Honkytonk Man has a warmth about it too, especially as Eastwood’s nephew is played by his son, Kyle. The Beguiled ranks among Clint’s most bizarre, experimental efforts, being a mix of horror, erotic drama and Southern Gothic.

It also finds Clint’s character being emasculated constantly by the women around him – another subversion of his manly screen image at that time. In the same Charlie Rose conversion, Eastwood admits he didn’t think Unforgiven would be a success either. The film pokes holes in the myth of the Old West, underling the ugly and lonely nature of taking another person’s life – even if they “deserve it.” On paper, Unforgiven’s demystification of the Western didn’t spell box office gold, but it was a critical and commercial darling upon release.

The Beguiled
was later remade by director Sofia Coppola in 2017, with Colin Farrell stepping into the Clint Eastwood role.

Only One Of These Eastwood Risks Was A Hit

Audiences didn’t exactly line up for Honkytonk Man in 1982

It’s interesting to track Eastwood’s career choices, where he seemed to balance commercial movies with more personal choices. He must have known something like Honkytonk Man wasn’t going to be a big earner, but that same year, Clint also directed effects-heavy blockbuster Firefox. This “One for them, one for me” work ethic served him well, but out of the three projects Eastwood considered his big risks, only Bronco Billy was a success, earning over $24 million at the domestic box office (via Box Office Mojo).

The Beguiled grossed only a measly $1.1 million, while Honkytonk Man just about doubted its $2 million production budget. It should be noted that the trio all received warm reviews, but it was Bronco Billy’s sense of whimsy and nostalgia that made it a comfortable success in 1980. It speaks to how big a star Eastwood was that he could get greenlights for projects that were almost destined not to perform well, though his reputation for turning in movies on time and for modest budgets probably helped alleviate those risks.

Bronco Billy Is Clint Eastwood’s Favorite Movie Of His Own

Eastwood loves the earnest message behind Bronco Billy

Bronco Billy feels largely forgotten now and rarely comes up in retrospective discussions of Eastwood’s back catalog. This is a pity because it functions both as a quirky drama about a dreamer and a reflection of its star’s own screen image. He has cited it many times as one of his personal favorites, and Clint labeled Bronco Billy’s underlying theme as one of “… a dreamer who made dreams come true“ (via TelevisionVanguard). In the movie, Billy tries to stay true to the cowboy ethos – but finds that easier said than done in a cynical modern world.

He and his gang want to live in a fantasy world, even when changing tastes and waning popularity threaten that way of life. Bronco Billy subverts Western formula at every turn too; Billy is left utterly humiliated when a tough sheriff forces him to beg for his friend’s release from jail, and the crew’s attempt to rob a train goes comically awry. It’s one of Eastwood’s sweetest efforts though, and it’s easy to see why he holds such fondness for it.

Clint Eastwood Has Taken Many Risks As An Actor & Director

Eastwood has rolled the dice constantly throughout his career

He might hold up The Beguiled, Bronco Billy and Honkytonk Man as prime examples, but looking at Eastwood’s filmography, it’s peppered with gambles. White Hunter Black Heart is a 1990 drama where Eastwood’s maverick director (inspired by the late, great John Huston) is obsessed with hunting an elephant while filming in Africa. It’s an intimate character study inside an expensive period drama, and while it grossed only $2 million on a budget of $24 million, White Hunter Black Heart is another of his most underrated works.

Every Which Way but Loose is Clint’s biggest movie – when adjusted for inflation – but he recalls everyone trying to talk him out of making it.

The Bridges of Madison County is an unabashed romantic weepie from 1995 – and one hardly aimed at Clint’s core fanbase. Regardless, the gambit paid off in great reviews and a healthy $182 million gross. Every Which Way but Loose is Clint’s biggest movie – when adjusted for inflation – but he recalls everyone trying to talk him out of making it. A comedy pairing him with a funny orangutan again didn’t feel like an obvious success story, but it beat bad reviews to become one of 1978’s highest earners.

Eastwood has taken many other risks, from the dark psychosexual thriller Tightrope to Midnight in the Garden of Good and Evil to supernatural drama Hereafter. At the height of his stardom, Clint Eastwood was completely willing to play with his screen image and stardom, which resulted in some of his most unique output.

Source: Charlie Rose, Box Office Mojo, TelevisionVanguard/YouTube, Rotten Tomatoes, The Numbers

• 

  Honkytonk Man follows a young boy during the Great Depression as he leaves his Oklahoma farm to accompany his country musician uncle, who auditions for the Grand Ole Opry. Released in 1982, the film explores their journey and the challenges they face along the way.

• 

  Bronco Billy is a 1980 Western comedy directed by and starring Clint Eastwood. The film follows Billy, a man who aspires to be a modern-day cowboy and leads a traveling Wild West show. Despite facing numerous difficulties and the eccentricities of his troupe, Billy strives to keep the spirit of the Old West alive. Sondra Locke co-stars as a troubled socialite who joins the show under unexpected circumstances.

• This film is set during the Civil War, focusing on a wounded Union soldier who takes refuge in a secluded girls’ boarding school in the South. His presence triggers a whirlwind of jealousy and betrayal as he manipulates the tensions among the sheltered women, leading to unexpected and dramatic consequences.