Sean Penn

Sean Penn earned his first Oscar nomination for his performance in Dead Man Walking (1995), later winning for Best Actor in 2003 for Mystic River. He starred in She’s So Lovely (1997) — winning Best Actor Award at the Cannes Film Festival — Milk (2008), Fair Game (2010), The Gunman (2015) and Licorice Pizza (2021).

Penn made his directorial debut with 1992’s The Indian Runner, followed by 1995’s The Crossing Guard and 2001’s The Pledge. He directed one of the 11 segments of 11’09”01 September 11 (2002) before receiving two Oscar nominations for his 2007 survival film, Into the Wild.

Penn previously married Madonna in 1985, splitting in 1989. Penn welcomed children Dylan and Hopper in 1991 and 1993, respectively, with Robin Wright. The two married in 1996 and split in 2007, but their divorce petition was later dismissed. Penn filed for legal separation in 2009, with their divorce being finalized the following year. He was married to Leila George from 2020 to 2022. Before dating Fast & Furious star Nathalie Kelley, Penn was linked to Charlize Theron and Olga Korotyayeva.