Sean Penn & Dylan Penn

Sean Penn is a multi-talented Hollywood personality. He started his career in the 1970s, but it was not until the early 2000s that Penn clinched prestigious awards. Sean won two Academy Awards for Mystic River and the biopic Milk. When he was 30, Penn began venturing in directing. He started his film directorial debut in 1991 for The Indian Runner. The success got followed by more films like The Crossing Guard, and The Pledge showed in the late ‘90s to early 2000s. He also takes the credit for the biographical drama Into the Wild in 2007, which gained nominations for Academy Awards.

Penn has two children Dylan and Hopper Penn, with Robin Wright. By age 30, Dylan is also making a name for herself—as an actress and a model. She has made modeling projects with Gap Inc. and is under Wilhelmina Models. Dylan also appeared in Nick Jonas’ music video for Chains.