Actor Michael Caine in Los Angeles.

The Retro Cool of Michael Caine

LIFE photographer Bill Ray looks back on his 1966 shoot with the up-and-comer.

It's 1966 and a young Englishman born Maurice Micklewhite is on the cusp of something big. Of course, nowadays audiences know him as Sir Michael Caine, the two-time Oscar-winner and star of films like "Hannah and her Sisters," "Batman Begins," and "Kingsman: The Secret Service." But back then, the 32-year-old was just coming into his own in Hollywood, thanks to turns in the spy flick "The Ipcress File" and the dramedy "Alfie" (for which he would earn an Oscar nomination). It was at this tipping point that celebrated LIFE photographer Bill Ray caught up with Caine, assigned to shadow the actor for a feature in the magazine (title: "Success of a Sometime Spy"). "Everybody was talking about Michael Caine suddenly," Ray recalls of his subject, whom he followed for a couple of weeks around Los Angeles as he filmed the movie "Gambit." "Today you'd say he's really cool. [He had] a real sense of humor. He thought it was pretty funny that Maurice Micklewhite, a cockney whose mother was a charwoman, was a genuine movie star. It was a hoot, you know." And what Ray captured is truly a moment in time — a portrait of a hot man-about-town letting his newfound success just sink in.

Here, in honor of Caine's 85th birthday (March 14), Ray relives the highlights of that long-ago shoot.

A Major Motion Picture Bill Ray A Major Motion Picture Ray spent many hours on set with Caine as he filmed the heist thriller "Gambit." In the movie, Caine plays a cat burglar who enlists the help of a showgirl (played by Shirley MacLaine) to pull off a risky caper. Though hardly a blockbuster, "Gambit" would go on to earn three Oscar nominations and a remake in 2012. At the time, it was clear Caine relished his time on set. "He'd rather be shooting a movie than anything else," Ray says. "A lot of actors don't like hanging around the set. Watching a movie [being] made is really like watching grass grow, but he was in his trailer and he had his recordings and he'd listen to the Four Tops or this or that." Carpool Bill Ray/The LIFE Premium Collection/Getty Images Carpool With his star rising, Caine was able to negotiate a few perks into his "Gambit" deal. Recalls Ray: "It was lunchtime and the commissary was a block or two blocks [away] — it was really close. [Michael] said, 'Bill, let’s go to lunch.' And I said, 'Great! We gonna walk?' He said, 'No, we don't walk. This Cadillac limousine is in my contract.'" [Laughs] "So we get in this limousine, the driver would take us about two blocks and we would get out." Circle of Friends Bill Ray/Getty Images Circle of Friends When not filming, the actor made the rounds in Hollywood, rubbing shoulders with the movers and shakers of his generation. Here he's seen with Sonny Bono and Cher — themselves breakouts thanks to the success of their hit "I Got You Babe" the previous year. Yet Ray doesn't recall photographing the singing duo alongside Caine. "Isn’t this something!" Ray said when shown the photograph. "Goddamn it. Sonny and Cher. Yeah. Wow. Some place like Jason's or one of those restaurants." Swinging Single Bill Ray/The LIFE Picture Collection/Getty Images Swinging Single Divorced from his first wife Patricia Haines in 1962, Caine was an eligible bachelor in 1966, meaning he spent a fair amount of time with pretty women — including Natalie Wood (seen here). Ray was well acquainted with Wood, having shot her own LIFE feature back in 1963. As to their relationship status, well, Ray didn't pry: "I don’t know what they were really doing." A Not-So-Modest Proposal Bill Ray/The LIFE Premium Collection/Getty Images A Not-So-Modest Proposal While Caine was a willing subject, there was one request he wouldn't entertain: taking off his shirt. Recalls Ray of Caine's reaction to a proposed shirtless tennis shot: "He said, 'I spent the last couple of years in a studio. I haven't been in the sun." Taking It All in Stride Bill Ray/The LIFE Premium Collection/Getty Images Taking It All in Stride Despite his growing fame, Caine was level-headed about his success, says Ray. "He just didn’t sweat anything." And why should he? After all, as Caine himself told the magazine, all he really wanted was out of his job at the neighborhood butter factory in London. "I set out to become the best possible actor I could," Caine said. "Never to be better than anybody and certainly not to become a movie star." And yet, movie stardom found him.