Reprise
The year 1960 had been a terrific one for Frank Sinatra. He was now making about $20 million a year through his film and TV production companies (Essex, Kent, and Dorchester), four music publishing companies, his gambling interests in Las Vegas and Lake Tahoe, radio partnerships, and his many real estate holdings. He also now had his own record label, the aforementioned Reprise. The problem with Capitol had been that he felt the label was restricting the way he recorded his music. He wanted to do it his way—select his own tunes, record at the times when he wanted to do so, schedule his releases when he felt they should be in the stores, and possibly even spearhead the careers of other recording artists—and he couldn’t do any of that as long as he was working for a label he didn’t own. It was agreed that after he finished his term at Capitol, he could lay the groundwork for a new label of his own. Frank told the media that he was now “a new, happier, emancipated Sinatra, untrammeled, unfettered, unconfined.” He was ready for 1961.
For Reprise, Frank was bursting with interesting concepts: a tribute to Tommy Dorsey; a string album; a concert album—so many ideas. Yet when he finally did get Reprise going, he started with an album indistinguishable from his Capitol work—Ring-a-Ding-Ding!, released in 1961.
The Ring-a-Ding-Ding! album is fun, but short on substance. Produced by Felix Slatkin and arranged by Johnny Mandel, it features the title track “Be Careful, It’s My Heart,” and “Zing Went the Strings of My Heart.”
As good as the Reprise albums were, none of them quite approached the matchless quality of Sinatra’s Capitol work. At the time, Frank was publicly critical of Capitol, especially after a legal battle when his former label began releasing product to compete with Reprise. But with Reprise he didn’t have people around him to provide the necessary feedback. When he started doing it all himself, something was missing.
At Capitol, the reins worked for Frank, not against him. Left to his own devices at Reprise, he would bring forth many good ideas, but none would be burnished to the level of the Capitol work. And as for the many remakes of Capitol songs he did at Reprise, many of them just didn’t equal the quality of the Capitol versions, whereas Capitol had successfully remade much of his Columbia material. And, significantly, Frank couldn’t resist playing around with the material in a jokey manner, as he did by adding a hip “And don’t tell your mama” to “Come Fly with Me.” Such self-indulgence in the studio was new for him, and not always appealing.
Still, in 1961 and 1962, Sinatra would record a plethora of material for the new label. In May 1961 alone, he recorded twenty-four songs, to be used on two albums, Sinatra Swings11 (arranged by Billy May) and I Remember Tommy (arranged by Sy Oliver).
The Tommy album is a tribute to Tommy Dorsey, and on it can be found some of Sinatra’s most evocative singing, especially “I’m Getting Sentimental Over You” and “Imagination.” Obviously, the music and its legacy was more important to Frank than any bad feelings between him and his former mentor. He believed the album was one of his better ones.
Also in 1961, in November, Frank would record the unforgettable Sinatra and Strings album, produced by Neal Hefti and Skip Martin. Don Costa’s striking arrangements of “Come Rain or Come Shine,” “Stardust,” and an extraordinary rerecording of Sinatra’s hit “All or Nothing at All” make this album a standout. It’s unique in that the sound is, by Sinatra’s design, more lush and grandiose than ever, with over fifty musicians in the orchestra.
What is considered by some to be his most emotionally complex album would be recorded in January 1962, All Alone. In her book about her father, Nancy Sinatra writes, “If you have this album and haven’t thought about it for a long time, play it now. It’s one of the best.”
Sinatra’s Preinaugural Gala
On January 6, 1961, John F. Kennedy sent his private plane, the Caroline, for Frank Sinatra and Peter Lawford so that they could spend the next two weeks in Washington planning the preinaugural gala. Drawing on a long list of his friends, Frank assembled a stellar cast for the gala, some of whom flew long distances to take part. Participants included Laurence Olivier and Ethel Merman, Leonard Bernstein, Sidney Poitier, Anthony Quinn, Joey Bishop, Louis Prima, Keely Smith, Juliet Prowse, Helen Traubel, Ella Fitzgerald, Gene Kelly, Nat King Cole, Milton Berle, and of course Sinatra. In what has to be one of the most astonishing cases of Frank doing it “his way,” his daughter Nancy Sinatra recalled, “Dad wasn’t fazed by the news that Olivier and Merman couldn’t make the date because they were appearing on Broadway in Becket and Gypsy, respectively. He just bought all of the seats and closed the shows for that night in both theaters.” Also, JFK, Lyndon Johnson, and Eleanor Roosevelt were scheduled to give speeches.
Prior to the festivities, Frank hosted a black-tie reception for the cast, the Kennedys, and the Johnsons in the Statler Hilton’s South American suite. Murray Kempton, of the New York Post, attended the party and wrote, “All these people, the Sinatras, Nat Coles, Gene Kellys—the most inescapably valuable collection of flesh this side of the register of maharanis—sons of immigrant or second-class citizens of not so long ago. They are in their wealth, their authority, their craft, the heirs of the Roosevelt revolution.”
Kempton could not have said the same thing about JFK himself. Sinatra certainly identified with Kennedy—both were liberal Democrats growing up with at least one parent deeply involved in politics, both Catholics, both womanizers, both the subjects of prejudice at one time or another, both overcoming odds to get to the top. Frank, whose loyalty to friends could sometimes border on the fanatical, had done a great deal to help Kennedy get elected. Tonight he basked in the glow of victory.
Like Frank, Jackie Kennedy also had a passion for detail when it came to organizing the event. She made specific plans to cover every aspect of the inauguration. The one thing she couldn’t control, however, was the weather. On January 19, almost eight inches of snow fell on Washington, D.C. Jackie had arranged to have buses pick up people at their hotels to transport them to the preinaugural party, but those plans were ruined when the transportation didn’t show up because of the storm. As a result, hotel lobbies became jammed with women in minks and men in dinner jackets, all trying, with no success, to get cabs to take them to the National Guard Armory.
The snow was so heavy that even the Kennedys were actually caught in a traffic jam. Frank was frantic that they might not show up at all. When, after ten, he heard that the Kennedys’ car was pulling up to the door, he rushed into the swirling snow to personally escort them inside. Taking Jackie by her white-gloved hand, he led her into the raised presidential box. She may have had ambivalent feelings about him, but she certainly did look radiant on his arm in her white satin Oleg Cassini gown with satin elbow-length sleeves. It was stunning in its simplicity, its only decoration a rosette of the same satin at her left waist. “It was a big moment for me, walking Jackie into that joint,” Frank would later say. “I’ll never forget the feeling.”
Sinatra’s gala got off to a rousing start at 10:40 p.m. when Leonard Bernstein raised his baton for the fanfare and “The Stars and Stripes Forever.” Mahalia Jackson sang the national anthem. Even though Ethel Merman had campaigned for Nixon, all was forgiven when she sang “Everything’s Coming Up Roses.” Frank’s reworded “That Old Jack Magic” drew hearty applause from the presidential box. Although the audience may have been smaller than expected, it did not lack enthusiasm.
People were still cheering the performers when JFK took the stage. “I’m proud to be a Democrat,” he intoned, “because since the time of Thomas Jefferson, the Democratic Party has been identified with the pursuit of excellence, and we saw excellence tonight. The happy relationship between the arts and politics which has characterized our long history I think reached culmination tonight.
“I know we’re all indebted to a great friend, Frank Sinatra,” he continued. “Long before he could sing, he used to poll a Democratic precinct back in New Jersey. That precinct has grown to cover a country.
But long after he has ceased to sing, he is going to be standing up and speaking for the Democratic Party, and I thank him on behalf of all of you tonight. You cannot imagine the work he has done to make this show a success.”
Frank Sinatra would say that he wanted the preinaugural gala to be “the greatest show ever.” He had certainly achieved his goal. In retrospect, January 19, 1961, was likely also one of the happiest nights of his life.
Sinatra Makes a Deal with the Devil
In late 1960, President John F. Kennedy appointed his thirty-five-year-old brother Bobby as attorney general of the United States. Sam Giancana told Frank Sinatra that this was a sucker punch he hadn’t expected. In Giancana’s mind, the only reason JFK gave his brother such a powerful position was because he wanted Bobby to “clear away all markers.” In other words, Giancana believed that JFK wanted Bobby to eradicate the very same underworld figures who had helped JFK get elected, thereby alleviating any future problems that might arise in terms of returned favors—and do it all under the guise of “a war on organized crime.”
In fact, organized crime was being investigated by the Senate and RFK long before the 1960 election. Bobby’s first investigations of Jimmy Hoffa had actually occurred while he served as majority counsel to the Kefauver Committee. “Would you tell us if you have opposition from anybody that you dispose of them by having them stuffed in a trunk? Is that what you do, Mr. Giancana?” Bobby asked Giancana at that time. Giancana declined to answer. “Would you tell us anything about your operations or will you just giggle every time I ask you a question?” Bobby pushed. Giancana still declined to answer. Bobby then said, “I thought only little girls giggled, Mr. Giancana.” It was a moment few would forget.
It is true, though, that when Bobby became attorney general, he turned the heat way up and was more eager than ever to eradicate all underworld activity from the United States—not just Giancana and his cronies. To that end, he instructed J. Edgar Hoover to mobilize the FBI’s resources. Bobby even recruited the Internal Revenue Service to step up its pursuit of certain syndicate figures suspected of tax evasion. Moreover, he appointed a committee to compile a comprehensive list of men to be investigated and prosecuted, some of whom were Frank Sinatra’s pallies—like Giancana, Mickey Cohen, and Johnny Roselli. But some were not, like Jimmy Hoffa and Roy Cohn.
Though not directed solely at Giancana, certainly none of Bobby’s pursuits were good news for him or for any of his rich and powerful underworld associates. Moreover, Sam had certain favors he had planned to ask of the Kennedys in the very near future, and he expected those wishes to be granted as a reward for his involvement in the successful West Virginia primary. Joe Kennedy had asked Frank to appeal to Sam to use his strong underworld connections to “encourage” the coal miners’ unions (and anyone else on whom they had influence in West Virginia) to vote for the Kennedy ticket. Not only had Sam done as requested, but he was successful in the venture—and wasn’t about to let anyone forget it.
In March 1961, Sam visited Frank at the Fontainebleau in Miami. He said he needed a big favor. “I need you to get Bobby Kennedy to back off of his investigation of me and my friends,” Sam said one night while he and Frank sat at the hotel’s bar. “This bullshit has to stop, Frank. You know it. And I know it.”
“I got no sway with that crazy Mick,” Frank said of RFK.
“Fine, then go to the old man,” Sam said, referring to Joe Kennedy.
Frank hadn’t been very happy when Joe Kennedy asked him to discuss the Kennedys’ problem in West Virginia with Sam Giancana. Now he was just as unhappy about Giancana’s request to appeal to the Kennedy patriarch. However, what was he going to do? Turn Sam down? “Don’t worry about it,” Frank said. “I’ll take care of it for you.”
“What’s your plan, then?” Sam wanted to know.
“I’ll start with the old man,” Frank said, taking a deep drag from his cigarette. “And if I can’t talk to him, I’ll talk to the man.” By the man, he meant the president.
Sam was delighted. “Okay, so we got a deal then, right?” he asked Frank.
Frank didn’t want to go quite that far. He just smiled and tossed back his drink. But as far as Sam was concerned, they did have a deal.
The Return of Marilyn Monroe
By the summer of 1961, Frank Sinatra, who was forty-five years old, and Marilyn Monroe, thirty-four, had known each other for about seven years. At the end of the 1950s, after their marriages ended—Marilyn’s to Joe DiMaggio and Frank’s to Ava Gardner—the two took solace in each other’s arms and ended up in bed together on a number of occasions. Marilyn continued seeing Frank from time to time, even during her marriage to Arthur Miller, from whom she officially separated at the end of 1960.
While Frank had romantic feelings for Marilyn, his relationship with her was not one to which he could ever become committed. Even after all this time, no one could take Ava’s place in his heart. Moreover, Marilyn had her own problems. As it had been in the 1950s when they lived together as roommates, Frank had no patience with women he viewed as either weak or vulnerable. Marilyn’s self-destructive nature and dependency on alcohol and pills bothered him now more than ever. Still, Frank was usually kind to her, and she appreciated that about him and had strong feelings for him because of it. Since she felt that she really wasn’t worthy of love—especially when she was in her midthirties and agonizing about aging—she always seemed to attract men who would use her and then discard her. At least Frank didn’t do that to her.
Renowned makeup artist George Masters recalled of his days working for Marilyn, “I would arrive at noon, and she’d still be in bed. Then she’d get up and start staggering around, groggy, and put on a Sinatra record. Then she would flop back in bed and tell me to keep changing the records. Always Sinatra records. Nothing else. I would stay there changing Sinatra records or talking to her, trying to bring her around.”
After a brief stay at the Payne Whitney Psychiatric Clinic in New York in February 1961, Marilyn wanted to spend some time in Los Angeles; that’s when Frank offered her his home in Bel-Air. However, at the last minute she changed her mind and decided against staying there, possibly in deference to Joe DiMaggio. She and Joe then enjoyed a vacation in Redington Beach, Florida, in March. Then, in June 1961, Frank invited Marilyn to Vegas. He was appearing at the Sands again and was also planning a party for Dean Martin’s forty-fourth birthday on June 7.
From Sands hotel interdepartment correspondence it can be gleaned that certain tactical decisions were made, partly having to do with Frank and Marilyn. One memo, from Entratter to Guzman and Freeman, dated June 5, 1961, states, “Please be advised that under no circumstances is any backstage photographer permitted to photograph Mr. Sinatra and Miss Marilyn Monroe together at the cocktail reception to follow the performance on June 7. Any photographer who attempts to do so will be permanently barred from the hotel. Be advised that this is not only a Sands requirement, it is a requirement of Mr. Sinatra’s and, as such, will be absolutely enforced. Thank you.”
Another memo, to “All Concerned,” dated June 6, 1961, says, “Marilyn Monroe will be Mr. Sinatra’s guest. It is Mr. Frank Sinatra’s intention that Miss Monroe be accorded the utmost privacy during her brief stay here at the Sands. She will be registered in Mr. Sinatra’s suite. Under no circumstances is she or Mr. Sinatra to be disturbed by telephone calls or visitors before two p.m.”
President Kennedy’s sisters Pat Lawford and Jean Smith were also present for the Las Vegas opening night, as were Elizabeth Taylor and her then husband Eddie Fisher, as well as Dean and Jeanne Martin, with whom Marilyn sat. (Dean wasn’t performing; this was a Frank Sinatra opening, not a Rat Pack engagement.) “She was beautiful, a vision with a great smile, lots of teased blonde hair, and a dress that was so low cut you couldn’t take your eyes off her bosom. However, she was also quite inebriated,” said a Las Vegas photojournalist who—along with a photographer for Wide World Photos—was one of the few reporters granted access to
the opening-night party in Sinatra’s suite.
“Oh, Frankie, c’mon, let’s make out for the photographers,” Marilyn said in front of the Wide World Photos lensman and the journalist. “I love you, Frankie,” she added, slurring her words, “and I want the whole world to know.” She was standing behind Frank and had her hands around his waist, as if she was leaning on him for support.
Frank pulled away rather than be photographed with her. When he did so, Marilyn almost lost her balance. He gave her a concerned look and told one of his bodyguards, “Keep an eye on her.”
Marilyn still wanted her picture to be taken with Frank. She sidled over to him like a kitten and motioned to the photographer with her index finger, indicating that he should take the shot while Frank wasn’t looking. She was being playful. Just as the photographer was about to take the picture, one of Frank’s bodyguards swooped in and grabbed the camera. He handed it to Frank and whispered something in his ear. Then Frank walked up to the photographer and the writer and hissed at them, “Next time you try that, I’ll crack your skull open with this camera, the both of ya.”
At that moment, Marilyn walked over to Frank with very uneasy footing. “Frankie, I’m gonna throw up,” she warned him. She didn’t look well.
Frank appeared alarmed. “When?” he asked.
“Now. Right now,” she exclaimed. “I mean it, Frankie!”
Frank rushed Marilyn out of the room as quickly as possible.
Sinatra Betrays Giancana
Eight months had passed since Frank Sinatra made the vague promise to Sam Giancana that he would talk to Bobby Kennedy about easing up on his investigation of him and his business associates.
In August 1961, Joe Kennedy contacted Frank once again. He wanted to reiterate his appreciation for Frank’s participation in the election and for helping to swing the West Virginia primary. He also again expressed his gratitude for Frank’s work on the preinaugural gala. He then extended an invitation from the president to entertain Sinatra at the White House. He also invited him to Hyannis Port, the family’s compound. Of course, Frank was very happy about all of this good news.
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