Written By: Liz Ronk

In the early- to mid-1960s, Dean Martin emerged as one of the most popular entertainers on the planet. He starred in major films, knocked the Beatles off the top of the charts with what would become his trademark tune, “Everybody Loves Somebody,” defined a new genre of cool with Frank Sinatra and the rest of the Rat Pack, and captained his own long-running TV variety show. He did all of it with the air of a man who had just woken from a nap and was still charmingly groggy.

In 1958 when the pictures in this gallery were made, Dino—while famous as one-half of the Martin & Lewis comedy duo—had not yet crossed over into superstardom. But he was certainly enough of a draw that LIFE magazine devoted a photo-filled seven-page feature to the man they dubbed “Make-a-Million Martin.”

[To] his skillfully used musical and comedy talents, he adds an ebullience that pervades everything he does. . . . Uninhibited, spry of mind and muscle, he maintains a state of relaxation that “makes Perry Como look like a nervous wreck.”

Keeping carefree appears to be the common denominator of the many Martins — showman, businessman, prankster, family man, self-styled hell-raiser and Hollywood social lion. In each role he works hard at making hard work look easy.

Here LIFE pays tribute to one of show business’ enduring, and most laid-back, superstars.

Dean Martin swung a golf club in order to stay loose on the set of the film Some Came Running, 1958.

Dean Martin swung a golf club in order to stay loose on the set of the film Some Came Running, 1958.

Allan Grant The LIFE Picture Collection/Getty Images

Dean Martin and Frank Sinatra, 1958.

Dean Martin and Frank Sinatra, 1958.

Allan Grant The LIFE Picture Collection/Getty Images

Dean Martin and Frank Sinatra, 1958.

Dean Martin and Frank Sinatra, 1958.

Allan Grant The LIFE Picture Collection/Getty Images

Sammy Davis Jr. visits Dean Martin and Frank Sinatra on the set of Some Came Running, 1958.

Sammy Davis Jr. visited Dean Martin and Frank Sinatra on the set of Some Came Running, 1958.

Allan Grant The LIFE Picture Collection/Getty Images

Dean Martin and Frank Sinatra, 1958.

Dean Martin and Frank Sinatra, 1958.

Allan Grant The LIFE Picture Collection/Getty Images

Dean Martin, Sammy Davis Jr.

Dean Martin and Sammy Davis Jr., 1958

Allan Grant The LIFE Picture Collection/Getty Images

Dean Martin with Shirley MacLaine, 1958.

Dean Martin with Shirley MacLaine, 1958.

Allan Grant The LIFE Picture Collection/Getty Images

Dean Martin listening to music at home, 1958.

Dean Martin listened to music at home, 1958.

Allan Grant The LIFE Picture Collection/Getty Images

Dean Martin in the steam room, 1958.

Dean Martin in the steam room, 1958.

Allan Grant The LIFE Picture Collection/Getty Images

Tuning up for work, after steam bath, Dean dines on beef and beer before Sands act. With him are songsmith Sammy Cahn (seated) and helper Mack Gray.

After a steam bath, Dean dined on beef and beer before his Sands act. With him are songsmith Sammy Cahn (seated) and helper Mack Gray.

Allan Grant The LIFE Picture Collection/Getty Images

Dean Martin, 1958.

Dean Martin, 1958

Allan Grant The LIFE Picture Collection/Getty Images

Japing for Judy [Garland], Dean charges onto stage, followed by Sinatra. To make amends for heckling Garland from audience, they contributed their talents to act.

Dean Martin charged onto stage, followed by Frank Sinatra, at a performance by Judy Garland. To make amends for heckling Garland from the audience, they contributed their talents to the show.

Allan Grant The LIFE Picture Collection/Getty Images

Dean Martin on stage, 1958.

Dean Martin on stage, 1958.

Allan Grant The LIFE Picture Collection/Getty Images

Dean Martin on stage, 1958.

Dean Martin, 1958

Allan Grant The LIFE Picture Collection/Getty Images

Dean Martin, 1958.

Dean Martin, 1958.

Allan Grant The LIFE Picture Collection/Getty Images

Dean Martin, Judy Garland and Frank Sinatra, 1958.

Dean Martin, Judy Garland and Frank Sinatra, 1958.

Allan Grant The LIFE Picture Collection/Getty Images

Playing host, Dean hosted dinner at his Hollywood Dino's Lodge restaurant. The menu before guest Edith Adams has been altered by her husband, TV's Ernie Kovacs.

Dean Martin hosted a dinner at his Hollywood Dino’s Lodge restaurant. The menu before guest Edith Adams had been altered by her husband, TV’s Ernie Kovacs.

Allan Grant The LIFE Picture Collection/Getty Images

Dean Martin 1958

Dean Martin advised Jimmy Van Huesen (foreground), Johnny Grant (left), Leo and Mrs. Durocher that the dinner would be “on separate checks.”

Allan Grant The LIFE Picture Collection/Getty Images

Dean Martin, Las Vegas, 1958

Dean Martin took a turn running a Sands roulette wheel. He pushed chips to a winner, telling her, “Either take it or get out of here.”

Allan Grant The LIFE Picture Collection/Getty Images

Dean Martin signing autographs, Las Vegas, 1958.

Dean Martin signed autographs, Las Vegas, 1958.

Allan Grant The LIFE Picture Collection/Getty Images

Dean Martin with his wife, Jeanne, 1958.

Dean Martin with his wife, Jeanne, 1958.

Allan Grant The LIFE Picture Collection/Getty Images

Dean Martin at home with his wife, Jeanne, 1958.

Dean Martin at home with his wife, Jeanne, 1958.

Allan Grant The LIFE Picture Collection/Getty Images

Dean Martin with Daughter, 1958

Dean inspected his daughter Claudia’s hair. ‘Comb it with a broom?” he asked.

Allan Grant The LIFE Picture Collection/Getty Images

Dean Martin and family, 1958

Young Dino flexed for his father, 1958.

Allan Grant The LIFE Picture Collection/Getty Images

Dean Martin and family, 1958

Pop’s perplexity was registered as Gina strolled pensively in shoes large enough for two.

Allan Grant The LIFE Picture Collection/Getty Images

Dean Martin at home, 1958.

Allan Grant The LIFE Picture Collection/Getty Images

Poker pals in a table stakes game at Martin's home include (clockwise from Dean at left) agent Jerry Gershwin, Tony Curtis, Milton Berle, Ernie Kovacs with 85-cent cigar, director Billy Wilder.

Poker pals at Martin’s home included (clockwise from Dean at left) agent Jerry Gershwin, Tony Curtis, Milton Berle, Ernie Kovacs with 85-cent cigar, and director Billy Wilder.

Allan Grant The LIFE Picture Collection/Getty Images

Dean Martin and son, 1958

Dean Martin gave his son Dino a kiss and a dish of ice cream. “Eat it, it comes on the dinner,” said Dean.

Allan Grant The LIFE Picture Collection/Getty Images

Dean Martin, Milton Berle

A Milton Berle joke slayed Curtis, Martin, and Warran Cowan. “Show Miltie a curtain, he takes a bow,'” said Dean.

Allan Grant The LIFE Picture Collection/Getty Images

Dean Martin with his wife, Jeanne, at home, 1958.

Dean Martin with his wife, Jeanne, at home, 1958.

Allan Grant The LIFE Picture Collection/Getty Images

LIFE magazine, Dec. 22, 1958.

LIFE magazine, Dec. 22, 1958.

LIFE magazine, Dec. 22, 1958.

LIFE magazine, Dec. 22, 1958.

LIFE magazine, Dec. 22, 1958.

LIFE magazine, Dec. 22, 1958.

LIFE magazine, Dec. 22, 1958.

LIFE magazine, Dec. 22, 1958.

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