Written By: Ben Cosgrove

 

“Forget the movie, let’s pull the job!”

That, legend has it, is what Frank Sinatra joked upon hearing the plot for Ocean’s 11, the 1960 Vegas heist flick that went on to become the Rat Pack’s signature big-screen adventure.

It’s no wonder Sinatra and his kindred crew of high-living, hard-drinking, skirt-chasing buddies, Dean Martin and Sammy Davis Jr., especially, were gassed to make such a movie: just like their characters, they loved a good caper. From the late ’50s until they began to splinter apart in the mid-’60s, they were showbiz’s unrivaled kings of swing, quick-with-a-quip cats who could swagger into any joint from the Sands to Sardi’s and make it the most.

[Buy the LIFE book, The Rat Pack: The Original Bad Boys.]

LIFE magazine’s photographers trailed the Pack through those smoky, magical years, coming away with priceless material for some of the best celebrity photo-essays the magazine ever ran. But of the thousands of shots taken, many were never published until now. Here, in celebration of sharkskin sits, Scotch on the rocks, smoke-filled rooms and fedoras tilted just so, LIFE presents a slew of rare photos of the Rat Pack, together and apart, during their boozy heyday.

Frank Sinatra and Dean Martin take a cigarette break during the recording of Sleep Warm in 1958.

Frank Sinatra and Dean Martin took a cigarette break during the recording of Sleep Warm in 1958.

Allan Grant Time & Life Pictures/Getty Images

Dean Martin smokes a cigarette beside his dressing room door backstage before his performance in Las Vegas in 1958. He adjusts his cufflinks.

Dean Martin smoked a cigarette beside his dressing room door backstage before his performance in Las Vegas in 1958.

Allan Grant Time & Life Pictures/Getty Images

Frank Sinatra and Dean Martinshare a light moment in the recording studio in 1958.

Frank Sinatra and Dean Martin shared a light moment in the recording studio, 1958.

Allan Grant/Life Pictures/Getty Images

Portrait of Frank Sinatra in cigarette and high ball glass at the Sands Hotel and Casino in 1964. He is wearing a bow tie and tuxedo shirt and sitting on a sofa.

Frank Sinatra at the Sands Hotel and Casino, where he sang with the Count Basie Band in 1964. Out of that landmark collaboration came the great live album Sinatra at the Sands.

Allan Grant/Life Pictures/Getty Images

Frank Sinatra and Joe E. Lewis walk through the kitchen to get to the stage at the Eden Roc Resort in Miami in 1958.

Frank Sinatra and Joe E. Lewis walked through the kitchen to get to the stage at the Eden Roc Resort in Miami in 1958.

John Dominis/Life Pictures/Getty Images

Sammy Davis Jr. eats spaghetti in his backstage dressing room in Golden Boy. Photographer Leonard McCombe is relected in the mirror.

Sammy Davis Jr. ate spaghetti in his backstage dressing room while watching The Huntley-Brinkley Report news show in 1964. “My only contact with reality,” he told LIFE. “Whatever I’m doing, I stop to watch these guys.” Reflected in the mirror: LIFE photographer Leonard McCombe.

Leonard McCombe/Life Pictures/Getty Images

Sammy Davis Jr. visits Frank Sinatra and Dean Martin at MGM Studios, where the duo were making Some Came Running in 1958.

Sammy Davis Jr. visited Frank Sinatra and Dean Martin at MGM Studios, where the duo were making Some Came Running in 1958. The movie co-starred Rat Pack “mascot” Shirley MacLaine, who years later would affectionately describe her old friends as “primitive children who would put crackers in each other’s beds and dump spaghetti on new tuxedos.”

Allan Grant/Life Pictures/Getty Images

Dean Martin entertains on a narrow stage with couples dancing around him in 1958.

Dean Martin entertained on a narrow stage with couples dancing around him in 1958.

Allan Grant/Life Pictures/Getty Images

Frank Sinatra offers a light in Sammy Davis Jr.'s Golden Boy dressing room in 1964.

Frank Sinatra offered a light in Sammy Davis Jr.’s Golden Boy dressing room in 1964. “It was six a.m. before the party got to Frank’s suite. But the evening was not over because Frank hadn’t said it was over. ‘Everybody have a little more gasoline,’ he ordered. Everybody did.” From “The Private World and Thoughts of Frank Sinatra,” LIFE’s classic photo-essay on the superstar, published in April 23, 1965

John Dominis/ Life Pictures/Getty Images

Sammy Davis Jr. in Golden Boy

Sammy Davis Jr. onstage during rehearsals for the Broadway musical Golden Boy, 1964.

Leonard McCombe/ Life Pictures/Getty Images

Sammy Davis Jr. plays with trumpet. The letters S and D hang on the wall behind him.

Though he often joked about his race, Sammy Davis Jr. (here fiddling with a trumpet in 1964) was a serious, high-profile civil rights activist, and his refusal to play segregated venues helped lead to the integration of Miami nightclubs and Vegas casinos.

Leonard McCombe/Life Pictures/Getty Images

Sammy Davis Jr. clowns backstage during Golden Boy's run in 1964. He bowtie is untied and his eyes are closed.

Sammy Davis Jr. clowned backstage during Golden Boy’s run in 1964. Davis once said, “As soon as I go out the front door of my house in the morning, I’m on, Daddy, I’m on! But when I’m with the group I can relax. We trust each other. We admire each other’s talent.”

Leonard McCombe/Life Pictures/Getty Images

Sammy Davis Jr. rests on his side with a pillow on the floor of a New York City hotel room. A hotel staff member stands in the background with a room service cart.

Sammy Davis Jr. rested on his side with a pillow on the floor of a New York City hotel room during the tour to preview Golden Boy in 1964.

Leonard McCombe/Life Pictures/Getty Images

ammy Davis Jr. counts money backstage during Golden Boy' s Broadway run in 1964. He is shirtless and wearing a do-rag.

Sammy Davis Jr. counted money backstage in Golden Boy, 1964. At the time he was being paid more than any Broadway star in history.

Leonard McCombe/Life Pictures/Getty Images

Dean Martin gets a massage at The Sands in Las Vegas in 1958.

Dean Martin had a massage at The Sands in Las Vegas, 1958. Said Martin once, “I can’t stand an actor or actress who tells me acting is hard work. It’s easy work. Anyone who says it isn’t never had to stand on his feet all day dealing blackjack.”

Allan Grant/Life Pictures/Getty Images

Frank Sinatra shaves in a steam room in Miami. He is wearing a towel around his waste and on his head. His face is covered with shaving cream.

Frank Sinatra shaved in a steam room in Miami.

John Dominis/Life Pictures/Getty Images

Frank Sinatra and Dean Martin drive a golf cart at Warner Bros. Studio in 1965 while making Marriage on the Rocks.

Frank Sinatra and Dean Martin tooled around the Warner Bros. lot while making 1965’s Marriage on the Rocks for the studio.

John Dominis/Life Pictures/Getty Images

Dean Martin and Frank Sinatra crack up during the Sleep Warm sessions in 1958.

Dean Martin and Frank Sinatra cracked up during the Sleep Warm sessions in 1958.

Allan Grant/Life Pictures/Getty Images

Dean Martin, Sammy Davis Jr., and Frank Sinatra pretend to be drunk on stage for a charity event in 1960.

Dean Martin, Sammy Davis Jr., and Frank Sinatra pretended to be drunk on stage for a charity event in 1960. After Martin fell, Sinatra put on a baseball cap and cried, “Safe!”

Allan Grant/Life Pictures/Getty Images

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