They quietly got engaged that December, but by the following June, it was revealed that the couple had ended their relationship. In early 2014, reports surfaced that Penn was dating a fellow Oscar winner, actress Charlize Theron. The couple divorced in 2010 in a non-amicable split. Seven years after his divorce from Madonna, Penn and House of Cards star Robin Wright wed in 1996. The book's publisher, Atria, followed with full-page ads in The New York Times and The Washington Post, in which snippets of critical quotes are countered with a teaser for positive reviews at the company website and a challenge to "read it and decide for yourself." Atria also issued a press release that questioned whether Penn was being given a fair chance to "expand his artistic profile" amid the "growing culture of divisiveness" in the country. That same year, he also starred in the critically acclaimed World War II drama The Thin Red Line, directed by Terrence Malick. In Hurlyburly (1998), Penn reprised a role he played on the Los Angeles stage in 1988.
Penn appeared in two other major films in 1997: the poorly received U-Turn, directed by Oliver Stone, and the hit action-thriller The Game, starring Michael Douglas.
Although Penn (who also served as executive producer) won the Best Actor Award at the Cannes Film Festival, She's So Lovely did not attract a wide audience. Penn next starred as a lovesick, jealous husband in Nick Cassavetes's She's So Lovely (1997), co-starring John Travolta and Penn's real-life second wife, Robin Wright. The film received positive reviews from critics, as well as a Golden Globe nomination for Anjelica Huston. 2015 The 87th Annual Academy Awards The Late Show with Stephen Colbert. Dogtown and Z-Boys Scene Smoking: Cigarettes, Cinema & the Myth of Cool: 2000 A Constant Forge. That same year, he wrote, produced and directed The Crossing Guard, a dark drama starring his boyhood idol, Jack Nicholson. (61 let) Santa Monica, California, USA Photo from. The film also did well with audiences, grossing more than $80 million worldwide. The film earned Penn Academy Award and Golden Globe nominations, as well as an Independent Spirit Award. With a penchant for gritty roles, Penns work began to earn critical acclaim in the 1990s. Penn made a concerted effort to distance himself from the teen genre altogether, selecting follow-up roles in such films as Bad Boys and The Falcon and the Snowman. In 1995, he starred as a death row inmate searching for salvation in the film Dead Man Walking, based on the true story by Helen Prejean. Sean Penn proven that his work in 1981s Fast Times at Ridgemont High was just the beginning of a brilliant career.