Jon Cryer – 55

You may remember Jon Cryer as Duckie in Pretty in Pink. He gained popularity for his earlier roles in films but it took quite a few years before he found true fame as a TV star. It all happened when he was cast in Two and a Half Men. With the success of that show, several other shows quickly followed as well as guest appearances. He’s married to Lisa Joyner, and they have an adopted daughter called Daisy. He’s looking great but has shared his difficulty with going bald.