Given the vast array of imaginative things that Hollywood is capable of crafting, it seems strange that moviemakers still struggle with some of the basics. Traditional makeup techniques that age actors stands as one of the biggest culprits and has often ruined entire films thanks to sloppy, weird, or unbelievable results. As many movies have proven, donning wrinkles and age spots doesn’t automatically equal a successful makeover. In the digital age, it’s easier for filmmakers to get a little help so that grandpa and grandma look more like live, actual people than a Halloween prop — but that’s what makes those who transform actors into senior stars old school-style so impressive. It’s an art form.

Leonardo DiCaprio underwent a dramatic transformation for the upcoming J. Edgar Hoover, and we definitely feel like it’s not one of his best-looking moments. The FBI’s first director didn’t win any beauty contests in his day, but DiCaprio appears to be drowning in his prosthetics, and the whole thing just seems awkward. This got us thinking about other cruddy elderly makeovers. Click past the break to see who made the leap to long in the tooth, in order from most convincing to least. Leave us your list in the comments. … Read More