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BOSOM BUDDIES. DEAN would call Frank “Pally” or “Dago”—as in “Dago, it’s time for bed,” because Martin wanted to sleep and get up early to play golf, while Sinatra was still shaking down the stars at three in the morning.

Sinatra wasn’t all that taken with Martin when he caught the Martin and Lewis nightclub act in June 1948: “The dago’s lousy, but the little Jew is great.” That view changed when both Frank and Dean were under contract to Capitol in the 1950s. The friendship grew to the point where Hollywood photographer Sid Avery said: “They’d have killed for each other. I’m not altogether sure they didn’t.”

The parallels in the careers of Sinatra and Dean Martin are not often discussed, though their friendship and professional collaborations are toasted and talked about.

Like Sinatra, Martin had to make a dramatic comeback. After the breakup of Martin and Lewis, the most successful comic act in America, Dino was in a funk. His life of lucrative moviemaking contracts and nightclub engagements had come to an abrupt end. No one thought he had a chance to make it as a singer, an actor, or as the host of one of the most popular TV shows of the 1960s and early seventies. That lay in the future. For the moment, Dean was up to his ears in debt, and his prospects were slim to none.

Like Sinatra in From Here to Eternity, Martin puts on a uniform in his comeback film, The Young Lions, where the headliners are Marlon Brando and Montgomery Clift but where Dino gives an altogether convincing performance as a vain entertainer who wants to dodge the draft and ends up a military hero at the Bulge alongside Clift, the same tormented Monty who acted alongside Frank in Eternity.

Frank’s friendship with Dean Martin ran longer than any of his marriages.
Allan Grant / Getty Images

A short time later, Martin read that Frank was looking for a guy to play a blackjack dealer in his next film. Dean thought, Hell, I smoke, drink, and play cards. I wouldn’t even have to act. “Frank laughed and said, ‘What do you know? You’re right.’ He hired me on the spot” for Some Came Running, another important moment in the resurrection of Dean Martin’s career.

By 1967 Dean had it made in the shade: he was making Matt Helm movies, comedies, and westerns, cutting records, cutting up on TV, making a lot of dough. Newsweek punned that he was “King Leer.” And he and Frank were best friends forever.

That said, let’s ponder the differences between the two.

Begin with the fact that Dean, aloof, liked being left alone, whereas Frank liked having a gang of guys around him. Frank blurred the line between art and life; Dean kept them in separate compartments. The drunk act, for example: Dean drank Martinelli’s apple juice, the color of scotch, on stage. (Said Frank, “I spill more than Dean drinks.”) Where Sinatra was ever restless and allergic to being alone, Dean Martin wanted to get a good night’s sleep. He threw a joint party for his daughter Deana (who was turning eighteen) and for the actress Jill St. John. The pop group Buffalo Springfield (lead singer Stephen Stills) was hired to perform. The party, Deana writes, was “fantastic” until the police came to break it up because neighbors complained about the noise. It wasn’t a neighbor who called. It was Dean.

Both Sinatra and Martin were great entertainers, talented actors. But one is really a singer at heart, the other a comic genius.

The reason Sinatra is a superior singer is the same reason that he is not as talented a comedian as his best buddy. One night at the Sands they decided to flip roles. Sinatra got all of Dean’s cracks, and Dean got the straight-man lines. And still Dean got more laughs. Frank: “How come no one’s laughing at me?” Dean: “Because you’re just not funny.” Deana Martin diplomatically says that Uncle Frank was “very funny,” but that her father was “a natural.” She’s right about her dad, but Dean was right about Frank: he was too serious, too intense, too dramatic, too much to be funny. If he got drunk enough he would do his Jimmy Cagney imitation (“You dirty rat”), which was even less funny than Jimmy Stewart imitating Cagney and sounding like Jimmy Stewart.

Sometimes Dean sacrificed music to theater, song to jest. He would begin a song: “You Made Me Love You.” And then, just when we’re expecting “you didn’t have to do it,” he would sing “you woke me up to do it.” Or he would take the Rodgers & Hart classic that goes “You are too beautiful for one man alone,” and continue, in the proper meter, with: “so I brought along my brother.”

The wit came naturally to Dean, who couldn’t take himself, or the entertainment racket, with high seriousness. Gifted with a baritone that was a bridge between the manner of Bing and that of Elvis, Dean could sing love songs beautifully. “Everybody Loves Somebody” displaced the Beatles at the top of the charts in 1964. He may have the best recording out there of “Just in Time.” And I have a great weakness for the songs he did with real or faux Italian: “That’s Amore,” “Volare,” “On an Evening in Roma.” But Dean could never do the “Soliloquy” from Carousel, or “Ol’ Man River” from Show Boat, or “Where’s My Bess?” from Porgy and Bess, or even “That’s Life,” and certainly not the song that begins “What is America to me?” All of these Frank sang for full dramatic effect. And it is not a question entirely of vocal range or power. Depending on your point of view, Dean lacked either the grandiloquence or the gravitas, or maybe he was just unwilling to suspend his sense of irony.

Sinatra—who couldn’t tell a joke to save his life, although the audience loved him and therefore laughed when he tried, just as they generously supplied the words to “The Second Time Around” when in a late concert he went up on the lines—had a self-conception that allowed him to sing songs of utmost seriousness, songs that brought a hush to the audience. He believed every word of “The House I Live In,” which he sang at the White House for Kennedy, Nixon, and Reagan. No reflexive irony stood in the way.

In 1953, Sinatra made what one of his biographers called four “suicide gestures.” One night, for example, Ava Gardner heard a gunshot and raced into Frank’s room. His body was lying across the bed, but he was all right; he had fired the revolver into the mattress (or the pillow). It is difficult to imagine Dean Martin either attempting or faking suicide. He liked being alone, and being left alone, which was the one thing that Frank couldn’t bear.