Skip to main content

Fly Me To The Moon

June 2024
27min read

Reflections on the Rat Pack
Everybody knows what they did. This is what they meant.


On January 19, 1961, at a gala in Washington’s National Armory on the eve of his Inauguration, President-elect John Kennedy made a remarkable gesture. He rose to tell the crowd, “We’re all indebted to a great fnettes—Frank Sinatra.”


On January 19, 1961, at a gala in Washington’s National Armory on the eve of his Inauguration, President-elect John Kennedy made a remarkable gesture. He rose to tell the crowd, “We’re all indebted to a great fnettes—Frank Sinatra.”

It was an act of legitimation, Camelot’s ;; first knighting: it marked the official ascendancy of Sinatra and, through him, of the rakish group of confederates known as the Rat Pack. For a few brief years the Rat Pack would be the swinging minstrels of Camelot, and the values and aspirations they embodied would have the imprimatur of presidential authority and enormous cultural cachet.

Just a year before, this unlikely group of entertainers, all loosely gathered around Sinatra, had been in Las Vegas to shoot a movie and do two nightclub shows each evening, spending most of the hours in between at all-night parties. Billed, with intentional swagger, as “the Summit” (a reference to the coming conference of Eisenhower, de Gaulle, and Khrushchev), their act took off like a rocket, its momentum carrying them beyond the three-week club date into movie and record and business deals, reprises in Miami, Atlantic City, and Palm Springs, power and influence unusual even for movie stars. The Rat Pack would do more than dominate show business. They would be both actors in and emblems of the carnivalesque, Janus-faced period called the Swinging Sixties, a postwar moment that staged the last stand of a half-century-old urban popular culture and contained the seeds of the suburban, post-ethnic America that would, in the course of that cataclysmic decade, supplant it.

On stage and off, the Rat Pack “swung” in every sense of the term, sending up the square world with a bravado that took mainstream the rebellious poses of rock and roll and predicted the sexual revolution we now associate with a different generation and a slightly later period. The Rat Pack announced that a new generation was laying claim to American tradition and to the right to define American Cool: one black, one Jew, two Italians, and one feckless Hollywoodized Brit, three of them second-generation immigrants, four raised during the Depression in ethnic city neighborhoods. Successful, self-assured, casual, occasionally vulgar, they were sign and symptom of what the war had done to the American WASP class system. The Rat Pack were more than entertainers, and the Summit was more than a stage act. It was a giddy version of multiethnic American democracy in which class was replaced by “class.”

When Bogart’s wife saw the drunken crew in the casino, she told them, “You look like a goddamn rat pack.”

No one understood how fragile it was. The brassy music, the camaraderie, the power, sex, and sharp male stylishness—it all depended on a potentially explosive mix of elements held together for a moment in a high-wire drama: Hollywood, Washington, D.C., and the Las Vegas underworld; white and black; sophistication and vulgarity; rebellion and tuxedoed respect for tradition, especially the Tin Pan Alley and theater song tradition that with the Rat Pack had its last run at the hit parade.

That night at the Armory was the zenith. In months the glue that held the complicated moment together would begin to dissolve.

Can’t We Be Friends?—Rat Pack Origins

Frank Sinatra and Dean Martin, like Perry Como and others of their generation, had cut their teeth on Bing Crosby’s intimate, crooning style, made possible by the microphone. Earlier singers trained in the music hall—Jolson, for instance—had been belters. Crosby sounded as if he were singing from his bedroom, and the younger performers learned from him new ways of using their voices to insinuate emotional nuance and sexuality. With Crosby, though, the sexuality, like the public persona, always remained polite and avuncular. Sinatra and Martin and the Rat Pack instead exuded machismo and danger, a style lent authority by their known associations with powerful and violent men. Postwar Americans had learned to take their popular culture spiked with a touch of risk, and Sinatra had molded his adult image on the sensitive tough guys portrayed in the movies by Humphrey Bogart.

Bogart in fact is central to Rat Pack history. In 1949 Sinatra had moved his family from L.A.'s Toluca Lake to Holmby Hills, just blocks from Bogart’s house, and the Hollywood rookie was inducted into a group of the film star’s drinking buddies. In June 1955 a dozen of them rented a train to catch Noël Coward’s opening act at the Desert Inn in Las Vegas: Sinatra, Bogart, Judy Garland, David Niven, the agent Irving (“Swifty”) Lazar, the composer Jimmy Van Heusen and his date, Angie Dickinson, and a few others. The story goes that when Bogart’s wife, Lauren Bacall, saw the drunken crew all together in the casino, she told them, “You look like a goddamn rat pack,” and they laughed. A few nights later at Romanoff’s restaurant in Beverly Hills, she repeated the wisecrack: “I see the rat pack’s all here.” Bogart thereupon formally founded the Holmby Hills Rat Pack, devising a coat of arms—a rat gnawing on a human hand—and a motto: “Never rat on a rat.” Frank was named Pack Master; Bacall, Den Mother; Garland, Vice President; Lazar, Treasurer and Recording Secretary. Bogart was Rat in Charge of Public Relations. He declared the Rat Pack was formed “for the relief of boredom and the perpetuation of independence. We admire ourselves and don’t care for anyone else.”

Sinatra liked having people around him, and after Bogart died in 1957, he assembled his own court. Some had been beneficiaries of Frank’s patronage. Joey Bishop, who grew up Joseph Gottlieb in South Philadelphia, the son of a bicycle repairman, was known as the Frown Prince of Comedy for his world-weary style. He had knocked around the burlesque and nightclub circuit for years when Sinatra spotted him in New York in 1952 and saw that he was booked on the same bill with him. Sammy Davis, Jr., was another. Singing with the Dorsey band in 1941, Frank had befriended the aspiring dancer, then part of the Will Mastin Trio; they reconnected after Sammy was discharged from the Army, and Frank helped the trio get work. In 1946 he insisted that New York’s Capitol Theater book the Mastins as his opening act at $1,250 a week, a sum that stunned Sammy’s partners.

Dean Martin had come up as a singer very much in Sinatra’s mold. In September 1943 reviewers touted a new act at New York’s tony Riobamba Club: “In Sinatra’s singing spot is a chap . . . who sounds like him, uses the same arrangements of the same songs and almost looks like him.” They didn’t meet until June 1948 after Martin had teamed up with Jerry Lewis, and the first impression didn’t impress. “The dago’s lousy,” Sinatra said, “but the little jew is great.” (Rather different was Louis B. Mayer’s assessment of the duo’s film prospects: “The guinea’s not bad, but what do I do with the monkey?") By the early fifties, though, the fellow Capitol recording artists had grown close, and they sealed their friendship in 1958 on the set of Some Came Running , which also featured the future Rat Packette Shirley MacLaine. In January 1959 Sinatra joined Martin for the first time on the stage of the Sands, setting the tone and format for the Rat Pack shows. Variety reported: “Martin, a heavyweight who appeals to both distaffers and their gaming escorts, sparks casino activity even if he doesn’t double as stage performer and blackjack dealer—which he usually does. First-nighters got an extra added attraction—Frank Sinatra joined his Great & Good friend onstage, and the pair put on one of the best shows ever seen at the Sands.”

It was a good thing, for the Sands, for Las Vegas, for the people whose money built all those modernistic hotels. Earlier that month Fidel Castro had marched into Havana and seized casinos that earned the mob millions annually. The pressure was now on Las Vegas, where the mob—with financing courtesy of the Teamsters Central States Pension Fund—had in the course of the 1950s invested in such new hotels as the Fremont and the Dunes. The Sands was the classiest, and it offered incentives to hold on to top talent. In 1958 Sinatra’s percentage in the hotel and casino was raised from two to nine points, and Dean Martin was sold a point. With Davis and Bishop already signed to long-term contracts, the Sands was the de facto home of the Rat Pack well before the Summit.

The fifth member of the Pack, suave, London-born Peter Lawford, was an actor and entertainer who had landed a contract with MGM when he was twenty but never broke into serious leading roles. By the late fifties he wasn’t doing much, but he had other assets: His wife was Jack Kennedy’s sister Pat. Sinatra chatted up the Lawfords in 1958 at a party at Gary and Rocky Cooper’s house, and they all got so close so quickly that when the Lawfords’ daughter was born in November of that year, she was christened Victoria Frances, for Uncle Jack’s re-election to the Senate that day and in honor of their new best friend. Sinatra clearly relished the Kennedy connection; his Rat Pack nickname for Peter was Brother-in-Lawford.

The Sands entertainment director agreed to a format for the Summit that fitted its improvisatory informality. For two shows each evening, at least one, perhaps two or three or four, sometimes all five entertainers, would appear on the Copa Room’s stage. The Sands would have its own gathering of top men. Although February was traditionally a slow month, the hotel received eighteen thousand reservation requests for its two hundred rooms. Word traveled fast about the Summit’s wildness—hijinks partially scripted and anchored by the emcee, Bishop, whom Sinatra called “the hub of the big wheel.” Between star turns by Martin, Davis, and Sinatra, and dance numbers with Davis and Lawford, they wandered off to the wings, parodied each other, did impressions, and poured drinks from a bar cart they rolled on stage.

They performed together, drank together, hung out together, and the press couldn’t get enough of them. At first they were called the Clan, over heavy protests. Sinatra said, “It’s just a bunch of millionaires with common interests who get together to have a little fun.” Bishop frowned: “Clan, Clan, Clan! I’m sick and tired of hearing things about the Clan. Just because a few of us guys get together once a week with sheets over our heads. . . .” Sammy Davis, straight-faced: “Would I belong to an organization known as the Clan?”

It was the sixties, and the resonances of clan were finally too disturbing given the growing awareness of the civil rights movement, so reporters reverted to the older name, and it stuck.


Like the Pony Express and the cattle drives, the Rat Pack’s legend seems all out of proportion to their fairly skimpy history. In 1960 there was the Vegas Summit, a Miami Summit at the Fontainebleau, a TV special featuring the much-ballyhooed first post-Army appearance of Elvis Presley, and the premiere of their first movie, Ocean’s 11 . That summer they sang the national anthem to open the Democratic National Convention in Los Angeles, and afterward they campaigned for Jack Kennedy. The movie finished the year in ninth place at the box office, behind Psycho , Spartacus , Exodus , La Dolce Vita , Butterfield 8 , and The Apartment . By 1962 Lawford was out, and a reduced Pack played Atlantic City and the mob-owned Villa Venice near Chicago. A second movie, Sergeants Three , opened. In 1963 came more shows at the Sands and the movie Four for Texas . In 1964 came the musical comedy-cum-gangster picture Robin and the Seven Hoods . That was pretty much it, except for a somewhat staid 1965 benefit for Father Dismas Clark’s halfway house for ex-cons, caught in a recently rediscovered kinescope, and a final 1966 “mini-Summit” at the Sands.

Nineteen sixty-one was the peak for the Rat Pack. Their pal was in the White House, Sammy got married, Sinatra and Martin were buying their own casino. They inspired a book and a television roundtable hosted by David Susskind. It was also the year Sinatra formed his own record company, Reprise, and brought the Pack over to it. In February, one month after Kennedy’s Inauguration, the first five albums were released, including Davis’s The Wham of Sam and Ring-a-Ding-Ding! , a great Sinatra record that captured the spirit of the era. The Rat Pack had their own argot: It was good to be Charlie or chicky baby , very bad to be a Harvey , and clyde was an all-purpose word, as in “Pass the clyde.” Ring-a-ding-ding was another Rat Pack phrase, which Sinatra first used in the 1961 song “Ring-a-Ding-Ding!” It was the sound, as Shawn Levy notes in his well-researched new book Rat Pack Confidential , of coins falling into the lap, of telephones bringing new offers of business or sex. It was the sound of brash self-confidence, of power, of the Rat Pack calling the shots, collecting the jackpot, of America reveling in its good fortune, its booming economy, and its sexy new world hegemony.

Sinatra relished the Kennedy connection; his nickname for Peter was Brother-in-Lawford.

The music, in which bells and chimes follow through on the ringing-and-dinging theme, provides the era’s ideal soundtrack. The brassy arrangements carry forward the full-throttled power, boldness, and insouciant humor of Sinatra’s late-fifties and early-sixties Come Dance/Swing/Fly With Me albums, but there’s a new jazzy informality and casualness in the singing: Sinatra had recently been on the road with the Red Norvo combo, and the small-group experience lent a new looseness to his sense of timing. Big and luxurious but light and flexible and spacious, the effect is of driving an expensive car down a highway with one hand on the wheel, Sinatra nudging it along with punched-out consonants and perfect syncopations (“Let! sss . . . fall in- love ”).

The combination of power with casual comfort, the stylish looseness, carried over to the Rat Pack’s act, which with its improvisations and combination of solo and ensemble work had analogs to jazz performance. They were swingers; like the Las Vegas club sound they helped invent, they combined a hip, sophisticated urban polish with the new informality of suburban living.

The Best Is Yet to Come

The Rat Pack is remembered for their style, their irreverent humor, their boozy and fleshy private lives, their leader’s occasional thuggish arrogance. But in their time they meant something else too, something that had everything to do with the expectations and aspirations of their audience. The key was ethnicity and the special role it played in postwar America.

The Tin Pan Alley culture from which Sinatra and friends emerged, and which they culminated, was created mainly by Jewish and other recent immigrants in the urban ghettos and was first interpreted mainly by black and Jewish musicians and performers—Sophie Tucker, Fanny Brice, Al Jolson, Louis Armstrong, and Ethel Waters, later Billie Holiday, Sarah Vaughan. By the late 1930s this culture was Italian as well. In 1939, the same year Harry James hired young Frank Sinatra to sing with his band, Ted Weems hired the former barber Perry (Pierino) Como, and the Columbus, Ohio, bandleader Ernie McKay hired a handsome young singing croupier named Dino Crocetti to front his Band of Romance.

For the Italians, as for the Jews and blacks before them, it was understood that ethnicity was a handicap you overcame. Never mind that the slangy, vernacular American song culture got its vitality from the tensions between urban immigrant street talk and “correct” diction. The Broadway social ladder was black to white, ethnic to WASP, lower class to upper. This had been Irving Berlin’s route, and Fred Astaire’s. Dino Crocetti is a case in point. For his first job, singing at a Columbus chop suey joint on a bill with Terry’s Six Wonder Dogs, bandleader McKay tried to cash in on the ethnic craze by changing his name to Dino Martini to echo the then popular singer Nino Martini. A year later, when he played the classy “ultramodernistic, intimate” Vogue Room in Cleveland’s Hollenden Hotel, that would no longer do. There bandleader Sammy Watkins (né Watkovitz) shortened the name to Dean Martin. Dino protested: What about Sinatra? He didn’t have to change his name. A freak shot, Watkins replied. “If Mussolini had declared war on England and France a week earlier, they would have changed the kid’s name to Frankie Williams.”

But Watkins was wrong. As Sinatra intuited, the war changed all the old assumptions. Faced with Nazism, Americans were rethinking their core ideals, and Sinatra lent himself to the effort. In 1945 he toured the country speaking at high schools against intolerance. As a centerpiece to the crusade, he produced and starred in a ten-minute docudrama, The House I Live In , in which he preaches lessons in ethnic harmony to a mixed-race gang of street kids. “My dad came from Italy, but I’m an American. Should I hate your father ‘cause he came from Ireland or France or Russia ? Wouldn’t that make me a first-class fathead?”


The film was commended by the National Conference of Christians and Jews, and it won Sinatra a special Oscar. He later told Edward R. Murrow that the Oscar meant more to him than the one he received for From Here to Eternity . He meant it. It was not with Bogart or in the Holmby Hills that the Rat Pack was conceived but in that mongrel gang of kids, teaching a lesson in American possibilities.

The Rat Pack show, unlike pre-war entertainment, featured—even flaunted—race and ethnicity. Bishop, dressed as a Jewish waiter, warns the two Italians to watch out “because I got my own group, the Matzia.” The night JFK showed up ringside, Dean picked Sammy up in his arms and held him out to the candidate: “Here. This award just came for you from the National Association for the Advancement of Col- ored People.” Sammy: “I’m colored, Jewish, and Puerto Rican. When I move into a neighborhood, I wipe it out.”

The vaudeville tradition that was the distant ancestor of their routines had relied on ethnic stereotypes: Irish and blacks, Germans and Jews, Italians and Poles—but as victims, as the lower-class butts of jokes. This was something altogether different, stars at the pinnacle of American entertainment who acted as if style and class and success were not at all incompatible with ethnic identification, whose act in fact proclaimed that they were truly American because they were Italian, or black, or Jewish.

It was as if that mixed-race gang of street kids from The House I Live In had learned the lesson about intolerance and grown up to embody it. Or, better, as if the World War II platoon of countless movies—Kowalski, Bernstein, Johnson, Maggio—had moved to Vegas; having beaten the Nazis, they would now conquer America.

The Rat Pack helped define what post-war meant, partly by allusions, overt and implicit, to World War II. Ocean’s 11 , the movie they worked on in Vegas between shows and cocktails—if work is the right word—was a heist-cum-buddy picture injected with hep talk and Playboy philosophy. Directed, presumably with clenched teeth, by veteran Lewis ( All Quiet on the Western Front ) Milestone, it is a bad but fascinating film in which Pack-plus-friends play an ex-platoon reunited for one final mission, stealing millions of dollars from five Las Vegas casinos, including the Sands.

The story reinforced associations already there. Except for Sammy, all the Rat Packers were linked to war pictures: Sinatra had his famous comeback in From Here to Eternity ; Martin first garnered respect as an actor in The Young Lions ; Sinatra got Lawford his first role in years in Never So Few ; and Joey Bishop was in The Naked and the Dead (“I played both parts” was his standard line). Like Ocean’s 11 , these stories were variations on that powerfully mythic multiethnic platoon. Now the war and its sacrifices were over, proclaimed both movie and stage act. Fitted out with tuxedos and bar carts, the old platoon, like their counterparts all over America, could guiltlessly grab for the money and pleasure that glittering Las Vegas symbolized—because success, fantastic American success, was the other side of the coin.


If their ribbing reminded audiences of their origins, if Dean’s singing “Volare” and “Arrivederci Roma” and Joey’s Jewish way of cracking wise and Sammy’s blue notes alluded to the old neighborhood, it was a neighborhood they and their audiences had succeeded in leaving behind. They had gone off to war from those overcrowded city streets and returned to buy houses in the new suburbs. They could relax a little and enjoy it, be Jewish or Italian or whatever, indulge in expensive cars or vacations, because the story of America was a kind of perpetual-upward-motion machine for every generation. And the second-generation immigrants on stage showed just how far, how fast, and how luxurious the ride could be.

The war and its sacrifices were over, their stage act proclaimed: Go and guiltlessly enjoy the fruits of victory.

The act worked because each of them projected a different attitude toward that aspiration and its success: Frank was the embodiment of slum kid become American classic; the others were foils. Dean, with what Variety called his “somebody wrote this song so I might as well sing it” attitude, suggested to the audience that the whole American success thing was a racket. Joey warded off envy with classic Jewish self-deprecating irony. Sammy, with his heartbreakingly perfect accent, turned every number into a drama of aspiration, giving everything to win over the audience, to have it accept and love him despite his race; the message was about overcoming odds. And Peter was the ultimate foil; he stood for the elegant but desiccated Anglophilic WASP culture whose day was over.

Philip Roth, in his novel of the postwar generation American Pastoral , describes this dream: “As a family they still flew the flight of the immigrant rocket, the upward, unbroken immigrant trajectory from slave-driven great-grand-father to self-driven grandfather to self-confident, accomplished, independent father to the highest high flier of them all, the fourth-generation child for whom America was to be heaven itself.” This was the other fantasy that the Rat Pack projected, the giddy, disorienting flight to American success. “The best is yet to come,” Frank sang, “and babe, won’t it be grand.” Fly Me to the Moon .

Early-sixties America, the writer Thomas Hine observes, was both obsessed with the future and preoccupied with America’s pioneering past. Disneyland had Frontierland and Tomorrowland. JFK had the New Frontier and the space program. The American suburban house had a futuristic kitchen and an Early American dining room, where families watched “The Jetsons” and “Bonanza.” The Rat Pack offered the same doubleness, at once exhilarating and reassuring: a past of the guys on the block, coming up the hard way, ethnic jokes and attitudes; a future of complete assimilation, wealth, swinging fun, and acceptance.

Me and My Shadow

Consider two standard ethnic jokes from the Rat Pack stage show: (1) Joey Bishop to Frank Sinatra: “Stop singing and tell people about all the good work the Mafia’s been doing.” (2) Frank Sinatra, offstage, to Sammy Davis: “Hurry up, Sam, the watermelon’s getting warm.”

The second “joke” makes for such unamused queasiness now, one wonders if audiences in 1960 really experienced the two remarks as equivalent. It’s impossible to know, because we stand on the far side of a watershed that was fast approaching, in which ethnicity (white) definitively diverged from race (black). American reality in the early 1960s moved so fast that in a very brief time the Rat Pack and the democratic vision they offered would go from daring to embarrassingly stereotypical. They hadn’t changed so much as been outrun.

What’s perhaps hardest to imagine now is how daring their interracial act still was in the Las Vegas of 1960. It was only five years since Davis himself, at the Last Frontier, and Harry Belafonte, at the Riviera, had broken the color line, finally permitted to use the facilities of the hotel and casino rather than be whisked from the stage to their rooms to wait until it was time for the next show. Typical of postwar conditions was the management of the Sands agreeing to drain the pool after some Southern guests saw Sammy swimming in it.

Sinatra, who practiced what he preached about intolerance, was a pioneer as well. Among the earliest proponents of civil rights in show business, he worked and traveled with black musicians, demanding equal treatment for all in restaurants and hotels. Even though Davis was already a star, his inclusion in the Rat Pack was a courageous move. Mixed-race acts were practically nonexistent.

The pressures fell of course mostly on Davis. When, in the summer of 1960, the Rat Pack took the stage to sing “The Star-Spangled Banner” at the Democratic National Convention in Los Angeles, the Mississippi delegation booed him, and he fought back tears. Frank whispered to him: “Those dirty sons of bitches! Don’t let ‘em get you, Charlie.”

As election time approached, the situation got uglier. When Davis’s fiancée, the Swedish actress May Britt, had come to see the Summit show, Sinatra bearded for him. But now that the wedding plans were public, racist demonstrators picketed him wherever he went. In early September, Davis decided to postpone their October wedding, after invitations had already gone out, to avoid embarrassing the best man, Sinatra, and through him the Kennedy campaign. (Sad as the gesture was, it was not paranoid. Nixon’s people had been making serious political hay out of the insinuation that Kennedy condoned interracial marriage.)

The bitterest blow came in January 1961. After Davis had tirelessly campaigned for JFK, the Kennedy White House asked him please not to attend the Inaugural festivities, which were being produced by Sinatra and other Rat Packers, because an interracial couple might offend elements among Kennedy’s political support.

When JFK was nominated, Sinatra slapped Lawford on the back: “We’re on our way to the White House, buddy boy.”

What the world never tired of reminding the Rat Pack was that race, in postwar America, was not the same as ethnicity. If ethnic identity for white Americans was increasingly symbolic and nostalgic, for blacks race was all too real. Soon the attacks came from the left as well as the right. As the sixties began to gather momentum, the simple fact of Sammy Davis’s inclusion, his symbolic integration in the gang, no longer made a statement. What stood out instead were the watermelon jokes, the Amos ’n’ Andy accents, Sammy’s demeaning role as comical cringing whipping boy. Civil rights would do to the Rat Pack’s implicit racial attitudes what it did, in a few short years, to the Swinging Sixties: make it seem a relic of a backward time.

James Baldwin, the prophetic conscience of the movement, sounded the note as early as 1960: “people . . . are always pointing out that So-and-So, white, and So-and-So, black, rose from the slums into the big time. The existence—the public existence—of, say, Frank Sinatra and Sammy Davis, Jr., proves to them that America is still the land of opportunity and that inequalities vanish before the determined will. It proves nothing of the sort. The determined will is rare—at the moment, in this country, it is unspeakably rare—and the inequalities suffered by the many are in no way justified by the rise of a few. . . . Furthermore, the American equation of success with the big times reveals an awful disrespect for human life and human achievement. This equation has placed our cities among the most dangerous in the world and has placed our youth among the most empty and most bewildered.”

For Sammy, the goal had always been his own pioneering inclusion: “Long before there was a civil rights movement I was marching through the lobby of the Waldorf-Astoria, of the Sands, the Fontainebleau, to a table at the Copa. And I’d marched alone. Worse. Often to black derision.” Now his consciousness began to change. Perhaps his last racially unself-conscious performance was the October 22, 1962, duet with Frank Sinatra of the old soft-shoe standby “Me and My Shadow,” with special lyrics and a witty Billy May arrangement: “We’re closer than smog when it clings to L.A. / We’re closer than Bobby is to JFK. . . . Our clocks don’t chime—they ring-a-ding-ding!”

Sammy was already a committed civil rights activist when, in August 1963, he joined Martin Luther King and a crowd of 250,000 at the historic rally in Washington, D.C. Two weeks later Dean Martin opened at the Sands, and Davis and Sinatra joined him onstage for some Rat Pack routines. “Sammy wanted me to march on Washington,” Martin joked. “I wouldn’t march even if the Italians were marching.” As the disparity grew, it ate like an acid into the humor and good spirits. By the time of the Dismas House benefit in 1965, Davis joked about asking Martin Luther King’s permission to appear, and said at one point, to uneasy laughter from the audience, “I been waitin’ back there so long I was about to call some troops.” He seemed angered by the old NAACP-award gag and by Sinatra’s bossiness. For the Rat Pack, as for the optimistic generation who idolized them, the realities of race seemed to have ended the good times, changed the rules. Davis would continue to perform with the Rat Pack, but from 1963 on he was more and more occupied with solo projects, including a Broadway production of the Clifford Odets play Golden Boy , rewritten as a musical with an interracial romance.

High Hopes

Despite the Rat Pack’s swank, ethnic version of American democracy, they still aspired to forms of authority and power more respectable and “serious” than those available through money and stardom.

One night a special guest came to the Las Vegas Summit. Frank stopped the show to introduce the glamorous young Massachusetts senator John Kennedy. Dean, allergic to politics and most forms of seriousness, broke in: “What did you say his name was?”

The connection between the Rat Pack and Kennedy was no secret, nor was it particularly surprising. Apart from Lawford, all the members had grown up in the urban neighborhoods that were the Democratic party’s strongholds; Sinatra’s mother, Dolly, was a ward boss in Hoboken. The Kennedys were only a generation or two removed from the world of the Irish families Sinatra, for one, had grown up with (his father had boxed under the name Marty O’Brien). It was not hard to see JFK, the Catholic son of a bootlegger, with his chic wife, Harvard polish, and now-respectable wealth, as a fully achieved version of the trajectory of assimilation. Besides, Kennedy’s macho liberalism had much in common with the tough, populist postwar progressivism that Sinatra had long espoused and that the Rat Pack embodied.

Peter Lawford was the key. He provided the personal connection to Kennedy that satisfied at one stroke Sinatra’s idealism and his attraction to power. In 1959 Senator Kennedy had extended a Los Angeles trip and stayed two nights at Sinatra’s Palm Springs estate.

Led by Sinatra, the Rat Pack threw themselves into the Kennedy campaign. Three weeks before the Summit, JFK announced his candidacy for the Democratic presidential nomination; his campaign song was “High Hopes,” the theme from Sinatra’s hit 1959 movie A Hole in the Head , with new lyrics by Sammy Cahn: “Everyone wants to back Jack / Jack is on the right track.” The association between politician and entertainers was so close that they were nicknamed the Jack Pack, and Time fretted that “some of JFK’s biggest headaches may well come from the ardently pro-Kennedy clique that is known variously as the Rat Pack or the Clan.”

Time didn’t know the half of it. JFK came to the Summit for something more than the music. Later he joined the Rat Pack upstairs in their rooms for drinks. Lawford whispered to Sammy Davis: “If you want to see what a million dollars in cash looks like, go into the next room; there’s a brown leather satchel in the closet. It’s a gift from the hotel owners for Jack’s campaign.”

Sinatra was playing marriage broker between the Kennedy campaign and another form of serious authority and power, the mob. Jack’s brother Bobby, chief counsel to the McClellan Senate committee investigating labor racketeering, had gone after Jimmy Hoffa and the Teamsters; in 1959 he called before the committee the Chicago mob boss Sam Giancana, an acquaintance of both Martin and Sinatra. Now the idea, apparently, was that if JFK could be elected with the help of donations from the Teamsters’ pension fund via Giancana, RFK could be persuaded to lay off. Besides, the parties had other common interests to discuss, like getting Castro out of Cuba.

More strange bedfellows were made that night. Sinatra introduced JFK to Judith Campbell, an ex-girlfriend whom he would also hook up with Giancana later that spring. The seeds were sown for a story that has a true sixties flavor: part paranoid political thriller, part bedroom farce, with a cast of entertainers, government officials, and gangsters that would break up the Rat Pack and scotch their bid for high social alchemy.

For two years things went like a dream. Unstinting with their time for personal appearances and Hollywood fund-raisers—twenty-eight hundred people showed up at a hundred-dollar-a-plate dinner at the Beverly Hilton for which Sinatra had turned out Davis, Lawford, Judy Garland, Angie Dickinson, Janet Leigh and Tony Curtis, Shirley MacLaine, Milton Berle, George Jessel, Joe E. Lewis, and Mort Sahl—the Rat Pack hitched themselves to Kennedy’s rising star. Sinatra, as bartender and greeter, watched the Democratic Convention with the Kennedys on television at Marion Davies’s mansion in Beverly Hills. When the Wyoming delegation put JFK over, he slapped Peter Lawford on the back: “We’re on our way to the White House, buddy boy.”

On November 8, 1960, the first Catholic was elected President of the United States. Skinny D’Amato, a mob connected Atlantic City club owner soon to be appointed manager of Sinatra’s own casino, the Cal-Neva Lodge, was heard to say, “Frank won Kennedy the election.” Sam Giancana saw it differently. “Listen, honey,” he told Judy Campbell, “if it wasn’t for me, your boyfriend wouldn’t even be in the White House.” On the stage of the Sands the following night, Dean Martin ad-libbed, “I just talked to Jack this morning and he made me secretary of liquor.”

Let’s hit Sinatra. Or I could whack out a couple of those other guys. . . .”

In January Sinatra and the Rat Pack—minus Martin, who always mistrusted Kennedy’s seductive embrace, and Davis—ran the National Armory gala. Bishop emceed, and the talent included Berle, Leonard Bernstein, Nat King Cole, Tony Curtis, Bette Davis, Jimmy Durante, Ella Fitzgerald, Gene Kelly, Ethel Merman, Laurence Olivier, Louis Prima, Anthony Quinn, and Carl Sandburg. Frank sang “That Old Jack Magic.” The gala raised two million dollars, defraying JFK’s campaign costs and paying off outstanding debts from Adlai Stevenson’s 1956 run. Kennedy told the crowd: “We’re all indebted to a great friend—Frank Sinatra. Long before he could sing, he used to poll a Democratic precinct back in New Jersey. That precinct has grown to cover a country.” Sinatra bought an ad in Variety to reprint the remarks and had them pressed onto a record. The following night the new President sneaked out of the official Inaugural ball to mingle with celebrities at an unofficial party Sinatra was throwing. Framed photos of the evening were later mounted in the “Kennedy Room” in Sinatra’s Palm Springs house.

That house was to host the jewel in Sinatra and the Rat Pack’s social crown: a presidential visit. In January 1962, just after Sergeants Three opened, JFK’s office announced that he’d stay there during a West Coast trip in March. Sinatra spared no expense: a new banquet room to seat forty, two cottages for the Secret Service, a communications center with extra telephone lines, a heliport, a flagpole. A plaque in the guest room was inscribed with Kennedy’s name.

It was,still great entertainment, but it was more about music and less about America.

But a fuse lit at the Vegas Summit was about to blow up in their faces. On February 27, 1962, J. Edgar Hoover sent a memo to Att. Gen. Robert Kennedy: Judith Campbell’s telephone records showed calls to both JFK’s personal secretary at the White House and Giancana in Chicago. RFK, alarmed and angry, knew where the problem lay, and he insisted his brother cut off relations with Sinatra and friends. On March 22, two days before the scheduled Palm Springs visit, Peter Lawford was told to inform Sinatra that the President would stay with Bing Crosby instead. When Lawford left the house, Sinatra grabbed a sledge-hammer and destroyed the heliport.

Though Sinatra cursed out Bobby Kennedy, Lawford took the brunt of it. “He felt that I was responsible for setting Jack up to stay at Bing’s—Bing Crosby, of all people—the other singer and a Republican to boot.” Sinatra never forgave him, and Lawford never performed again with Sinatra or any other member of the Rat Pack.

Any illusion of Sinatra’s influence with the Kennedys evaporated. “He can’t get change for a quarter” is how Giancana put it, who felt Sinatra owed him and who was having trouble getting performance dates out of the Rat Pack for his clubs. “Let’s show ‘em,” one of Giancana’s men says to him in a secret FBI recording. “Let’s show those asshole Hollywood fruitcakes that they can’t get away with it as if nothing’s happened. Let’s hit Sinatra. Or I could whack out a couple of those other guys. Lawford and that Martin.” “No,” Giancana replies, “I’ve got other plans for them.”

In November, Sinatra, Martin, and Davis played three free nights for the grand opening of the remodeled Villa Venice, Giancana’s restaurant and casino in Northbrook, Illinois. FBI agents interviewed them in their suites at the Ambassador East Hotel. Sinatra said he was performing as a favor to the owner, Leo Olsen. And Sammy? “Baby, that’s a very good question. But I have to say it’s for my man Francis.” “Or friends of his?” “By all means.”

All that was left of the astonishingly hubristic attempt to marry the dark, powerful forces of ethnic past and the new might of American present was indebtedness to the dark side. Moreover, the rift with the Kennedys began a drift away from the buoyancy of the early sixties and would culminate on the day in November 1963—the Rat Pack was filming the graveyard scene in Robin and the Seven Hoods —that the President was assassinated in Dallas. Sinatra didn’t attend the funeral. “It just wasn’t possible to invite him,” Lawford said. “He’d already been too much of an embarrassment to the family.”

With the end of Camelot, the high spirits and the high hopes the Rat Pack embodied seemed somehow off the point. Sinatra, Martin, and Davis would continue to perform together—Bishop’s services were no longer required as the act evolved away from its loose free-for-all—but became increasingly invested in their solo careers: Frank went from Leader of the Rat Pack to Chairman of the Board, Sammy became the Golden Boy, Dean became Matt Helm and got his own TV show. They were bigger successes than ever, but the heart had gone out of it. When they did work together, the improvised Army buddy camaraderie gave way to a rehearsed show business routine. It was great entertainment, funny, riveting, swinging, but it was more about music and less about America.

The Last Dance

Or, rather, what “America” meant was changing, and fast. The pivotal year was 1964. In January, while “Dean Martin & Friend” performed at the Sands with a bar cart on the stage, a Capitol record titled “I Want to Hold Your Hand” hit the charts. Two months later Bob Dylan released “The Times They Are A-Changin'.” Martin himself introduced the Rolling Stones on a TV special that year.

A new generation was flexing its cultural muscles, and to it, the sixties would mean not Vegas and Miami, casual suburban luxury, and postwar success, but civil rights and Vietnam. For the newcomers the tuxedoed Rat Pack with their smirks and highballs evoked not the giddy upward flight of successive generations who hoped to scale the walls of the Establishment but the crass materialism that made the Establishment the horror it was.

The rock music that defined the new culture was a radical break from the Rat Pack’s modernism: earnest rather than sly, naive rather than sophisticated, “countrified” rather than urbane, striving for a rough authenticity rather than a swinging polish. In this new culture, ethnicity seemed old-fashioned and irrelevant; it was meaningless to ask what the ethnic background of the Byrds, the Beach Boys, or Jefferson Airplane was. In music, as in other aspects of suburbanizing post-modern America, the multifariousness of ethnicity would be eclipsed by the polarity of race.

For a number of years the two cultures coexisted. Dean Martin’s biographer Nick Tosches tells how, a few days after “The Times They Are A-Changin'” was released, Martin confidently set to work on a new album. His twelve-year-old son, Dino Jr., was a Beatles fan. “I’m going to knock your little pallies off the charts,” Martin told him. A few months later “Everybody Loves Somebody” unseated the Beatles’ “A Hard Day’s Night” as the number one hit record. In 1967, the year of the Summer of Love, Martin had the number one Nielsen TV show. In 1968 Reprise had three gold albums: Jimi Hendrix’s Are You Experienced and two Dean Martin records.

But it was a last hurrah. Sinatra as usual was the first to sense the shifting of cultural winds, and for the third time in his career, he brilliantly reinvented himself. His 1965 hit “That’s Life” appropriated the bluesy sound of Ray Charles’s organ and backup singers to fashion a new white blue-collar soul that was about survival within the system rather than opting out or changing it. It perfectly anticipated the moment when many Democratic, white, post-ethnic Americans would abandon their traditional political affiliations to create a powerful neo-conservative Republicanism. It is a straight line from there to Sammy Davis’s famous embrace of Richard Nixon in 1972 to Martin’s and Sinatra’s joining their former political adversary John Wayne in support of Gov. Ronald Reagan. In 1985, twenty-four years after producing Kennedy’s Inaugural celebration, Sinatra was back in D.C. to produce Reagan’s.

In the meantime, though, it was the newcomers who were winning the culture war, assisted by the fact that the Rat Pack’s swinging, cavalier attitudes toward sex shaded so easily into callous indifference to women. In 1972 Life magazine called Dean Martin’s TV show “the witless reign of King Leer": The sexual humor was “calculated degradation.” In 1973 the National Organization for Women named Martin’s show, along with Last Tango in Paris , winner of the Keep-Her-in-Her-Place award. Within a year it was off the air.

In Vegas and Atlantic City, Sinatra and Martin were still heroes to their traditional audience. But to the new generation the Rat Pack, who a few years earlier had epitomized racy, progressive cool, were macho boors whose patriotism masked a self-serving complacency.

There’s irony in the fact that the Rat Pack, like the cocktail and the cigar, has lately been taken up as an emblem of a new political incorrectness. The drinking, the smoking, the swinging insouciance seem like a vacation from the economic and political pressures of nineties America.

But there is more to the Rat Pack than adolescent swagger, more even than the sharp-edged dash of their masculine style, though they had plenty of both. For a few short years America’s greatest entertainers kidded and sang their way through our last cultural consensus.

Who’s Who in the Rat Pack

Enjoy our work? Help us keep going.

Now in its 75th year, American Heritage relies on contributions from readers like you to survive. You can support this magazine of trusted historical writing and the volunteers that sustain it by donating today.