Shawn Levy - Rat Pack Confidential

For Sammy, to whom the clubbiness and fame of showbiz were brass rings worth one’s very soul, it was a stunning sight. “I couldn’t take my eyes off him, walking the streets alone, an ordinary Joe who’d been a giant. He was fighting to make it back again but he was doing that by himself, too. The ‘friends’ were gone with all the presents and the money he’d given them. Nobody was helping him.”

There were others who sensed Sinatra’s pain and tried to help. L.A. gangster Mickey Cohen, an admirer of the singer’s (“If you call Frank’s hole card,” he said approvingly, “he’s gonna answer”), tried to rally his spirits by hosting a testimonial dinner for him at the Beverly Hills Hotel. Instead, the sparsely attended event simply underscored Sinatra’s dilemma. As Cohen recalled in his hilarious autobiography, “A lot of people that were invited to that Sinatra testimonial, that should have attended but didn’t, would bust their nuts in this day to attend a Sinatra testimonial. A lot of them would now kiss Frank’s ass after he made the comeback, but they didn’t show up when he really needed them. I don’t know the names of a lot of them bastards in that ilk of life, but I remember the people that I had running the affair at the time telling me, Jesus, this and that dirty son of a bitch should have been here.”

At the time, Frank wasn’t really keeping up with all the snubs—he was far too bewildered by life with Ava and the prospect of resuscitating his career. But he was still Dolly’s boy, and he had to have noticed the slights. And if he’d ever shown himself to be curt and exclusive before bottoming out and being left behind, when he recovered he became more demanding than ever of the loyalty of those he allowed around him. Only the surest would be abided.

Such a one was Humphrey Bogart, the movie god whose blessing upon Frank was one of the lifelines that kept him hopeful that he might someday emerge from the straits in which fate had left him foundering.

In all Hollywood, nobody had a flintier or more enviable reputation than Bogart. An Upper West Side sissy boy who went from playing juvenile walk-ons to psychotic killers, paranoid adventurers, and cynics with soft hearts, he danced just within the boundaries of the game. His drinking, womanizing, and bellicosity never quite made the front pages, his bad-mouthing of bosses never quite stooped to insubordination, and his liberal political beliefs and headstrong independence never quite severed him from the basis of his wealth, fame, and popularity. The one potential faux pas of his life—his affair with starlet Lauren Bacall—was easily cast by studio flacks and gossip mavens as a great May – December romance, especially after the couple wed and started a family.

For a large part of the movie colony, Bogie was a cult hero—a Knight of the True Way. He did his work best by being something that no one else could be: himself. Off-camera, he drank away afternoons in restaurants, went out of his way to upset prigs at parties, cruised the Pacific on his sailboat, and made, with his young wife, a home that offered haven to those very select few in his business who, like him, weren’t fooled for a minute by their own press.

Nothing, but nothing, rattled Bogart more than the sight of Hollywood kissing its own behind, especially over unproven new talent, and especially unproven male talent that was rooted in alleged sex appeal. So in 1945, when the jug-eared boy singer who made the bobby-soxers wet their pants showed up in town to great foofaraw, Bogart was ready to dismiss him out of hand. They ran into one another for the first time at the Players, the Sunset Boulevard restaurant, bar, and theater owned by Preston Sturges.

“They tell me you have a voice that makes girls faint,” said Bogart, an expert needler. “Make me faint.”

Sinatra stood right up to him: “I’m taking the week off.”

Bogart liked the response, liked the kid. And Frank, of course, saw in Bogart all the things he always wanted to be: aloof, profound, world-weary, slightly drunk, slightly sentimental, romantic, tender, tough, loyal, and proud. (He could take his hero worship too far. Once, when a date of Frank’s declared, in Bogart’s presence, “You sound like Bogie sometimes,” the actor laughed and said, “Don’t remind him, sweetheart, the poor bastard’s trying to kick it!”) He tried to cajole producers into casting him in Knock on Any Door as a tough street kid opposite Bogart’s impassioned lawyer; such was Sinatra’s stock as an actor that the role went to John Derek.

Nevertheless, the two men got into the habit of spending time together whenever the occasion arose, which, given Frank’s hectic schedule of filmmaking, recording, and touring, wasn’t often. In 1949, though, Frank moved his family from Toluca Lake to Holmby Hills, just blocks from Bogart’s house. This new proximity allowed the two stars more frequent contact; soon after moving into the neighborhood, Sinatra organized a guys-only baby shower for Bogart when Lauren Bacall was pregnant with their first child.

The relationship got a little strange. After Frank had left Nancy and the kids, he was still welcome in their house; he would frequently crash on his estranged wife’s couch after nights of bingeing with Bogart, shuttling between the two homes as if, in his mind, they constituted one. “He’s always here,” Bogart told a reporter. “I think we’re parent substitutes for him, or something.” Bacall empathized with Frank’s need for companionship, but Bogart warned her against getting wrapped up in it. “He chose to live the way he’s living—alone,” he admonished his wife. “It’s too bad if he’s lonely, but that’s his choice. We have our own road to travel, never forget that—we can’t live his life.”

In fact, Bogart was one of the few people who were willing to tell Frank exactly what they thought of some of the things he did. There was the time he hosted Sinatra, David Niven, and Richard Burton for a night of drinking on his beloved yacht, Santana. Frank was at a career ebb, and he passed part of the night on deck, serenading yachters on the other boats moored nearby; Bogie grew so irate with Sinatra’s preening performance, recalled Burton, that he and Frank “nearly came to blows.”

There was the time when Frank, riding high on the early reviews for From Here to Eternity , visited his hero in search of approval. “I saw your picture,” said Bogie. “What did you think?” Frank asked. Bogart simply shook his head no.

And there was Bogart’s famous line about Frank’s thin-skinned egoism: “Sinatra’s idea of paradise is a place where there are plenty of women and no newspapermen. He doesn’t know it, but he’d be better off if it were the other way around.”

Still, there was a bond between the two: father-son, mentor-acolyte, king-pretender—somehow the dynamic was agreeable to them both. They both reviled the traditional cant and decorum of Hollywood protocol, they both had deep political concerns for the everyman, and they both loved to needle people, especially the thin-skinned twits their lives as famous performers gave them so many chances to meet. Frank was always welcome in the Bogart home; the Bogarts, in turn, accepted his hospitality when he would want to scoop up a gang of pals and run off for a weekend in the Springs or Vegas.

In June 1955, for instance, he gathered a dozen or so chums, rented a train, and took off to catch Noel Coward’s opening at the Desert Inn (yes, that Noel Coward and that Desert Inn; Vegas was always great with novelties). During that particular spree, legend has it, the group had gotten so deep into its cups that Bacall was startled by their debauched appearance when she caught a gander of them ringside in a casino showroom. She looked around at all the famous flesh—Frank; Bogart; Judy Garland; David Niven; restaurateur Mike Romanoff; literary agent Swifty Lazar and his date, Martha Hyer; Jimmy Van Heusen and his date, Angie Dickinson; a few well-oiled others.