Dylan Penn & Sean Penn

The first husband of Madonna, and a prolific actor, Sean Penn, has contributed a lot to the entertainment industry. Having started his career in the ’70s, Penn is widely famous for his roles on Mystic River and Milk, for which he won Academy Awards.

Between 1996 and 2010, Penn was married to the fellow actress Robin Wright, with whom he shares two children. One of them is Dylan Penn, a daughter who is now a model and actress. Dylan posed for GQ, W, and Elle magazines and is one foxy 29-year-old. Of course, she has both her parents to thank for her successful career.