mainly because he was taking on an uncharacteristically comedic role. The man who started the decade by playing hardboiled cop Harry Callahan in Don Siegel's seminal action thriller, "Dirty Harry" was wrapping it up by playing truck driver Philo Beddoe, a guy who lives in a small San Fernando home with his orangutan buddy Clyde. The film sees Philo embark on a cross-country adventure in search of a woman he believes is his soulmate. On his trip he's accompanied by Clyde and his brother/manager Orville (Geoffrey Lewis), with the trio managing to get into all sorts of trouble as they track down Sondra Locke's Lynn Halsey-Taylor.

It doesn't exactly sound like the kind of thing Eastwood would go for, does it? In fairness, Philo wasn't a role entirely devoid of the tough guy persona Eastwood was known for. The man made money on the side by bare-knuckle boxing, and over the course of the movie takes on everyone from biker gangs to LAPD cops (and wins). But there's no doubt this film was an outlier amid the Eastwood oeuvre and critics were merciless in their appraisal. That said, the movie made quite a surprising amount of money and the veteran actor certainly had a good time with his animal co-star.