In 1958, Clint Eastwood threatened to stop acting after a screening of his movie Ambush at Cimarron Pass. “It was so bad I just kept sinking lower and lower in my seat,” he recalls. “I said to my wife, ‘I’m going to quit, I’m really going to quit.’”

Luckily for the world’s movie lovers, he hung in there. A short time later, CBS hired him to play Rowdy Yates on the western series Rawhide. Clint didn’t love his noble character, but the part brought him financial security, a chance to fine-tune his acting and the opportunity to observe the art of directing. “I’ve never had a plan, in my career as an actor or a director,” admits the four-time Oscar winner. “Things would just pop up and I’d get a feeling about them.”

Clint’s instincts proved largely to be right (although he did turn down Martin Sheen’s role in 1979’s Apocalypse Now). The star, 93, is currently working on the courtroom thriller Juror #2. “They say this is probably his last film, but I wouldn’t hold my breath,” says a friend. “He’s older, he tires a little quicker than he used to, but he can still keep up with the rest of the cast and crew. Filming doesn’t stress him out, it actually relaxes him.”

Likewise, Clint’s private life has rarely been happier. The twice-divorced father of eight adult children has been happily coupled with Christina Sandera since 2014. “He’s not looking for another marriage, and Christina understands that,” says the friend. “They like to have nice dinners, take walks, watch films, documentaries, stream certain shows — that’s pretty much it.”

Following the cancellation of Rawhide, Clint accepted the starring role in A Fistful of Dollars, a western filmed in Spain by then little-known director Sergio Leone. “I decided it was time to be an antihero,” says Clint, who helped hone the character of the mysterious Man With No Name, whom he’d play in three films. Although initially dismissed by critics, these “spaghetti westerns” would make Clint an international movie star.

For the remainder of the 1960s, Clint continued to branch out and take chances. There were more westerns, war epics and even his career’s only musical, 1969’s Paint Your Wagon, costarring fellow tough guy Lee Marvin. The open-minded actor also accepted the guest role of the villainous Two-Face on TV’s Batman, but the campy superhero series was canceled before Clint filmed his first scene.

Clint Eastwood answers phone while wearing a suit
Hulton Archive/Getty Images

The 1970s brought fresh opportunities. Clint directed his first feature with 1971’s thriller Play Misty for Me — for which he was paid scale. “To be honest, I would have been willing to pay them!” says Clint, who also starred in the film. It became a modest hit and a wonderful learning experience. “I felt that directing made me much more sympathetic to what directors have to do. I was easier to work with as an actor after I’d directed a few times,” he says.

The same year, Clint played Harry Callahan for the first time in Dirty Harry. A critical and commercial success, the 1971 film would spawn four sequels. “I felt the character was a man of purpose,” says Clint. “Once he decided on something, there were no side movements away from it, no extraneous movements. He was a very determined soul.”

In Clint’s post-Harry career, he took more chances, like starring in the romantic Bridges of Madison County with Meryl Streep. He is among only a handful of living directors who directed two Best Picture winners (1992’s Unforgiven and 2004’s Million Dollar Baby). Clint also scooped up Best Director Academy Awards for both. The second award, when Clint was 74, made him the oldest person to win a Best Director Oscar.

His private life, which includes spending time with his children and five grandchildren, is also a source of happiness and pride. “He has definitely chilled out. He likes to have fun and see the kids,” his daughter Alison, an actress and director, tells Closer. “When we were growing up, he was doing back-to-back movies. It’s been great that he has been able to spend a lot of time at home and more time with the kids, grandkids and the girlfriend. That’s one of the perks of getting old.”

Clint isn’t a particularly introspective man, but he can’t deny that it’s been an amazing ride. He believes that the key to his success has been a willingness to take chances. “Go for it, otherwise you miss great opportunities to enjoy yourself and have fun,” he says. “Sometimes you have to swing hard and miss the ball. But you have to swing hard.”