5. Clint Eastwood - Pink Cadillac (1989)
Pink Cadillac was a particularly dark blemish on Clint Eastwood's stellar film career. This 1989 action-comedy attempts to give Eastwood an opportunity to display his comedic talents. There is little to show off here, as Eastwood seems lost in the role. Eastwood stars as a skilled bounty hunter, which gives him the opportunity to dress up in disguise as many different characters to catch his prey. Pink Cadillac seems to have no comedic guidance whatsoever from Eastwood in the leading role, and clocking in at over 2 hours, it is a dry and lifeless effort. Eastwood once again follows the creed that if a tough guy is willing to show a sensitive side it makes for built in laughs, right? What he makes up in his tough guy roles (Dirty Harry, The Good The Bad & The Ugly) can be redeemed from Eastwood, but hopefully he discovered that the comedy well is rather empty after the debacle that was Pink Cadillac.