The following article was published in the Feb. 27, 2015 issue of Entertainment Weekly.

Kirk Douglas — the beloved screen legend who turned 98 in December — never tires for great conversation, especially when the subject is moviemaking and how to survive it. (One tip: Drag your hotshot director to therapy.) We invited the actor, still blessed with the playful masculinity and moral fiber of the Old Hollywood icon that he is, to reminisce about four of his greatest roles.

Spartacus (1960)

Credit: Everett Collection

Douglas’ most indelible role — as a Roman slave leading an epic rebellion — is also the one that best allowed him to flex his muscle within Hollywood. “Spartacus represents all people who work for freedom,” he says, noting that as a producer he’d hired blacklisted writer Dalton Trumbo to pen the film under a pseudonym. “Then I decided — the hell with it! I’m going to put his name on it. That’s the thing I’m most proud of. It caused me a lot of trouble, but it was worth it.” Douglas admits there was a limit to the freedom even he could exhibit on set, though. “There wasn’t much to my outfit,” he laughs, referring to his wardrobe-malfunction-prone tunic. “I had to be careful. But I’m always careful.”

The Bad and the Beautiful (1952)

Credit: Everett Collection

Douglas earned one of his three Best Actor nominations (he got an honorary Oscar in 1996) for this acid-bath melodrama about Hollywood. “Usually it’s difficult to make a movie about making movies, and to make it believable,” he says. But the characters here, especially Douglas‘ supermacho studio boss, are so venal that when one dies, extras are hired to attend his funeral. “I think the film is a very realistic story about Hollywood,” he jokes.

Paths of Glory (1957)

Credit: Everett Collection

In this extraordinary antiwar movie, Douglas stars as a colonel in the First World War who refuses to command his soldiers into a bloodbath. It’s as fresh, relevant, and technically dazzling — check out those tracking shots in the trenches — today as it was six decades ago. Douglas credits the film’s then-28-year-old director, whom he handpicked, for that: “The picture made Stanley Kubrick. He was such a talent, but very difficult and troubled. Sometimes he confided in me, so I had an idea: Why don’t we go see a psychiatrist together? And we went. The psychiatrist was very impressed with Kubrick’s mind and ended up pitching a film idea to him.” More than 40 years later, that idea became Eyes Wide Shut, the director’s final project.

Ace in the Hole (1951)

Credit: Everett Collection

“It’s a very good film, but the critics gave it unkind reviews,” he says of Billy Wilder’s ink-black exposé of the media, which cast the actor as a journalist. “But I think it was because it was about an unscrupulous newspaperman and that hit too close to home.” In preparation, Douglas hung out in a New York City police station. “It was a rainy, cold day and someone was lying down in the courtyard. I asked, ‘What’s that?’ They told me, ‘Oh, that’s a dead guy. We’re trying to figure out who he is.’ I don’t know if they ever found out. Maybe he’s still there.”

—Reporting by Natasha Stoynoff