Roger Ebert was no stranger to Clint Eastwood’s work. As one of the most respected film critics of all time, he frequently praised Eastwood’s films, calling The Good, the Bad, and the Ugly a masterpiece and awarding four-star reviews to Unforgiven, Mystic River, and even the divisive Flags of Our Fathers. But when Eastwood stumbled, Ebert wasn’t one to hold back—and in 1989, he absolutely tore into Pink Cadillac, branding it “idiotic.”
By the late ’80s, Eastwood had built a reputation for mixing rugged action with lighthearted humor. Sometimes it worked (Thunderbolt and Lightfoot, Every Which Way But Loose), and sometimes it flopped (Firefox, City Heat). Hoping for another hit, Eastwood teamed up with The Dead Pool director Buddy Van Horn for Pink Cadillac, a quirky action-comedy that should have been a harmless crowd-pleaser. Instead, it left Ebert—and much of the audience—scratching their heads.
The film follows Tommy Nowak (Eastwood), a bounty hunter with a knack for disguises, tasked with tracking down Lou Ann (Bernadette Peters), a woman on the run after stealing from her criminal boyfriend. The twist? Her boyfriend is a member of a violent white supremacist gang out for revenge.
Ebert’s biggest gripe was the movie’s tonal confusion. On one hand, you have Eastwood goofing around in disguises and trading witty banter with Peters. On the other, you have a sinister subplot about a racist militia. It was, as Ebert put it, a bizarre combination: “This silliness might work in a movie like Every Which Way But Loose, but Pink Cadillac has a disturbing subplot about a secret army of white racists—and so the comedy seems out of place.”
If the tonal clash wasn’t enough, Ebert also slammed the film’s nonsensical plot. Characters made frustratingly dumb decisions, seemingly just to keep the story moving. One scene, in particular, drove him up the wall: when Nowak captures one of the white supremacists, he promises to dump him a mile down the road for safety. Instead, he drops him 25 yards away, putting himself and Lou Ann right back in danger. “How can we take a thriller scene seriously when the characters don’t?” Ebert fumed.
Beyond the script’s flaws, Ebert was simply uncomfortable with how the film treated its villains. He argued that white supremacists weren’t just another batch of disposable bad guys for an action-comedy. “There are many serious, nuanced films about the racism that has always been at the dark heart of America,” he wrote. “Using a group of white supremacists as the throwaway villains in a light little action-comedy seems inappropriate.”
Unsurprisingly, Pink Cadillac bombed at the box office and was largely dismissed by critics. Even Eastwood himself later admitted that not all of his films hit the mark. “I go back and look at films I’ve made, and I could easily ask, ‘Why the heck did I make this?’” he once reflected. But true to form, he didn’t dwell on failures.
Eastwood would bounce back in the ’90s with some of the best films of his career—Unforgiven, In the Line of Fire, and The Bridges of Madison County—proving that even after a misstep, a true legend knows how to get back on track.
