5. Clint Eastwood – Paint Your Wagon (1969)
For a time, Clint Eastwood was unarguably the edgiest character in Hollywood.
Having made his name as a gruff action star in Westerns and cop movies alike, Eastwood still maintains some semblance of his tough guy status despite his advancing years and decades having passed.
And, while many believe Paint Your Wagon to be nothing more than a joke from The Simpsons, it is undoubtedly a real movie, and it makes for truly bizarre viewing. Seeing everyone’s favorite hard-talking, hard-staring gunslinger singing his way across the Wild West is truly something to behold, and not in a good way.
It’s hard to believe a gruff character like Eastwood would ever consent to being in such a campy, whimsical piece of musical cinema, but Paint Your Wagon remains on Eastwood’s back catalog as a strange outlier among his more serious, gritty roles.