Emilio Estevez the History Boy
Thirty-one years later Estevez returned to the 84-year-old grand hotel for a publicity photo shoot for his film Rated X. Despite his early Hollywood success, the former Brat Packer was struggling after a failed marriage, disappointing movies and money woes. While standing in that lobby, however, he felt inspired. "My whole childhood came back," says Estevez, 44, of revisiting the Ambassador, since demolished to build a high school on the site. "I remembered where I was when Bobby was shot [and] being there later with my father. It was like somebody unlocked the padlock to my memories."
Estevez channeled that flashback into Bobby, the new film he wrote and directed about the Ambassador on the day of Kennedy's death. The project also gave him the chance to reunite with fellow Brat Pack alum Demi Moore. Engaged in the '80s, the two play a feuding husband and wife. "She and I have seen each other socially over the years," says Estevez, who wrote the role of an alcoholic lounge singer specifically for Moore. "But to work with her, man, was old home week." Moore, 44, agrees. "There was something very natural" about fighting on camera with her ex, she says. "Intense as the scenes were, we were laughing all day." Estevez also found a part as a hippie for Moore's husband, Ashton Kutcher. "Emilio and I were on the phone and he said, 'Do you think Ashton might do this?'" recalls Moore. "I said, 'Let me pass him the phone.'"
Estevez worked on the script for five years, packing his movie with A-listers (see sidebar). "This was a passion for him," says cast member Elijah Wood, who plays a teenager trying to avoid Vietnam combat by marrying a girl he doesn't love, played by Lindsay Lohan. But it's been a long trip back to the big time. The eldest son of Martin and Janet Sheen, Estevez rose to fame in such movies as The Breakfast Club and St. Elmo's Fire. After having two children (son Taylor, 22, and daughter Paloma, 20) with model Carrey Salley, he began dating Moore and later wed Paula Abdul in 1992. They divorced two years later. By then, his career had stalled. "Mighty Ducks one—I probably should have stopped there," he says. "I started to answer to a different god. I had a very expensive now-ex-wife and got caught up with bigger is better—I went broke chasing that."
To clear his debts Estevez sold his home, autographed photos and cashed in his pension. With Bobby he hopes those days are behind him. His personal life is also on the rebound. In September he became engaged to journalist Sonja Magdevski, 34. They plan to wed "hopefully soon," he says.
He's already got plenty to celebrate—not the least of which is giving voice to his memories. "I've had a lot to say for a long time and no one to say it to," says Estevez. "I've never been more broke in my life, but I've never been more fulfilled."