Clint Eastwood And Jim Carrey Crossed Paths In This Forgotten '80s Comedy

Clint Eastwood's reputation as a legendary big screen tough guy persists even while he's managed to become one of the most respected directors in Hollywood. When we think of the man who directed "Million Dollar Baby" and "Unforgiven" we also can't help but think of the Man with No Name and "Dirty" Harry Callahan. But the actor played many more diverse characters than he gets credit for and took on several roles that casual fans of the man might not expect.

In 1978, for example, Eastwood made the then-controversial decision to star in "Every Which Way but Loose" opposite a trained orangutan named Manis. The action-comedy saw him and his co-star travel across the United States in search of a woman Eastwood's character has convinced himself is his soulmate — and wouldn't you know it, the movie was a hit, spawning the 1980 sequel "Any Which Way You Can," which saw Eastwood and his ape buddy team up once again. The sequel wasn't quite as successful and took a drubbing from critics. But its star had already proven he could handle comedy with "Every Which Way but Loose," which represented a big change of pace for an actor who'd started the decade playing rugged rogue cop Harry Callahan in "Dirty Harry." Regardless of how the sequel performed, then, audiences had already responded favorably to Eastwood playing against type, and he thereafter dabbled in more lighthearted fare.

Unfortunately, not every comedy Eastwood fronted after that hinge moment in his career performed as well. Take 1989's "Pink Cadillac," in which the veteran star portrayed a bounty hunter with a proclivity for elaborate disguises. The action-comedy saw Eastwood re-team with "Any Which Way You Can" director Buddy Van Horn and, once again, the results weren't great. Critics did not take kindly to the movie, though it did at least give us an undeniably funny scene in which the gruff Eastwood encounters a young Jim Carrey doing what the comedian does best.

Jim Carrey and Clint Eastwood actually crossed paths for the first time in 1988's "The Dead Pool," one of the worst of the five "Dirty Harry" movies. In this final film in the franchise (unless you count the spiritual sequel "Gran Torino"), Carrey can be seen playing a heavy metal frontman whose most memorable scene involves lip-synching to "Welcome to the Jungle" in a music video homage to "The Exorcist" directed by Liam Neeson. (You might be starting to understand why the film was received so poorly.) Carrey doesn't last long in the movie and doesn't have any scenes with Eastwood, but he'd get another chance to work with the veteran star a year after "The Dead Pool" debuted.

In "Pink Cadillac" Eastwood's Tommy Nowak tracks down Bernadette Peters' Lou Ann McGuinn, who has skipped bail and absconded in the titular vehicle along with some money belonging to a group of white supremacists. He finds her in a casino and sits down at a table while a comedian performs on-stage in the background. That comedian is Carrey, who can even be heard delivering an early rendition of his now classic Ace Ventura line "Alrighty Then" in the film.

As Nowak and McGuinn chat, the camera cuts to Carrey doing his schtick, which, in this instance, is an Elvis tribute performed with his arms tucked inside his shirt. Eastwood scowling at Carrey prancing around on-stage is inarguably funny and seems to represent exactly how the actor would feel if he encountered Carrey's antics in real life. It very much has the same energy as Tommy Lee Jones' famous rebuke of Carrey during the filming of "Batman Forever," in which he told the then-young star that he could not "sanction" his "buffoonery." In this brief scene in "Pink Cadillac," that's pretty much what I imagine Eastwood is thinking. Sadly, the rest of the movie isn't as funny.

"Pink Cadillac" was the third collaboration between Clint Eastwood and director Buddy Van Horn, who, aside from directing "Any Which Way You Can," was also responsible for "The Dead Pool." That's not exactly the finest contribution to Eastwood's celebrated oeuvre (though Carrey's music video performance in the latter is one of the greatest "Dirty Harry" movie moments), but at least with his 1989 action-comedy the filmmaker had finally succeeded in bringing Eastwood and Jim Carrey together in a single scene. Otherwise, "Pink Cadillac" was mostly dismissed by critics, though some found it charming enough.

The movie fared only slightly better than the 20% score for "Any Which Way You Can" on Rotten Tomatoes, with a 24% critic score based on 21 reviews. Roger Ebert found the movie dull and its tone uneven, writing, "There's little that's new in the material, and nobody seems to have asked whether the emotional charge of blatant racism belongs in a lightweight story like this — even if the racists are the villains." Similarly, Caryn James of the New York Times described the film as "the laziest sort of action-comedy," with "lumbering chase scenes, a dull-witted script, and the charmless pairing of Mr. Eastwood and Bernadette Peters." If anything, it would have been better to team Eastwood with Carrey and let the two clash throughout — especially since one of Carrey's best early impressions was of a "Dirty Harry"-era Eastwood.

Still, some were quite taken by "Pink Cadillac" with Jonathan Rosenbaum of the Chicago Reader seemingly having seen an entirely different movie. He wrote in his review, "As a deeply personal work about free-floating existential identities, this 1989 film has the kind of grit and feeling that few action-comedies can muster, with Eastwood and Peters interesting and unpredictable throughout."