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.
