In Sinatra: The Chairman, the second of James Kaplan's two acclaimed, doorstop-sized biographies of Ol' Blue Eyes, the author identifies the first person to refer to Frank Sinatra, Dean Martin, Sammy Davis Jr and friends as "The Rat Pack". This was New York-based journalist Dorothy Kilgallen, a syndicated gossip columnist for the Hearst newspaper group. The term had previously been applied to actor Humphrey Bogart and his alpha-male pals, but it was Kilgallen who put it in print and applied it to Sinatra and co.
The Hearst papers and Sinatra had been at loggerheads in the US since the 1940s. Hearst writers had picked up on the singer's marital infidelities and his ties with the Mafia. Kilgallen, a woman who Sinatra once unchivalrously called "that chinless broad", took some pleasure in using The Rat Pack description. She knew that naming Sinatra and friends after a species of vermin would irk the singer – and it did. Even as late as 1987, some 30 years after The Rat Pack's glamorous heyday, Sinatra rebuked a reporter at a press conference for using "that stupid phrase".
The singer's preferred name for his carefully vetted male inner circle had been "The Summit" or "The Clan". But Davis Jr, a generous financial supporter of the Civil Rights Movement – and an Afro-American whose comedy regularly mocked the white supremacism stance of the Ku Klux Klan – was never comfortable with "The Clan".
For better or worse, The Rat Pack name stuck, and in the intervening years, the term has become shorthand for a kind of unflappable cool that, musically at least, has stood the test of time. Think of The Rat Pack and we think of style and pizzazz; of larger-than-life song-and-dance men who were charismatic all-round entertainers.
But as many commentators after Kilgallen have observed, The Rat Pack was certainly not without its spells of men behaving badly. In their pre-political-correctness social climate, a competitive machismo and a degree of misogyny sometimes reared their ugly heads. Further, the race-related gags that were sometimes directed at Davis Jr onstage hurt him, even if he felt it necessary to pretend otherwise at the time.
When Sinatra, Martin and Davis Jr performed together on the Las Vegas casino circuit of the 1960s, backed by the impeccable jazz musicians of the Count Basie Orchestra, they were a huge draw. Concertgoers who couldn't secure hotel rooms would sleep in their cars or in hotel lobbies rather than miss out. The fact that The Rat Pack's appearances together were often impromptu lent the events an air of chance. One famous billboard at the Sands Hotel and Casino read: "Tonight: Dean Martin. Maybe Frank. Maybe Sammy."
If all three showed up, crowds felt that they had lucked-out, but the shows would only last for an hour or so at most. The casinos knew that the audiences were full of high-rollers, and didn't want them away from the slot machines and roulette wheels for too long. Especially because The Rat Pack's members didn't come cheap as performers.
Immaculately groomed and tailored, Sinatra, Martin and Davis Jr would engage in knockabout comedy routines that were part-improvised. There were impressions, too, and Davis Jr was a fabulous dancer and probably the best all-round entertainer of the three. The all-star trio's main currency, though, was song. And what gifted crooners they were, and what an extraordinary back catalogue of songs for swinging lovers they tapped into. Cole Porter's I've Got You Under My Skin; Bart Howard's Fly Me to the Moon; Rodgers and Hart's The Lady Is a Tramp; Cory and Cross's I Left My Heart in San Francisco. These and countless other numbers from Great American Songbook were brilliantly orchestrated for The Rat Pack's live performances.
Though everyone from Robbie Williams to Rod Stewart to Harry Connick Jr has by now made a crooner album tapping Rat Pack-friendly material, the best medium for exploring this legacy is undoubtedly musical theatre. The natural theatricality of the original Rat Pack's Vegas shows and the films Sinatra, Martin and Davis Jr went on to star in together (such as Ocean's 11 and Sergeants 3) all point to this.
When the Dubai Opera welcomes The Definitive Rat Pack show on July 3 and 4, it will be playing host to a production that had its premiere in London's West End in 2003, and had further acclaimed runs there in 2009, 2011 and 2017. The show was nominated for an Olivier Award and went on to tour Europe and the US. To date, the production has been seen by more than 10 million people.
Stephen Triffitt, Mark Adams and George Daniel Long – the three British performers who respectively play Sinatra, Martin and Davis Jr – have by now spent a considerable chunk of their lives playing their alter egos. They are reportedly as close as one can get to the original Rat Pack without use of a time machine.
When David and Victoria Beckham wanted a headline act for their sons' christenings at "Beckenham Palace", they booked Triffitt in full Sinatra mode, while, as Dean Martin, Adams has played the Royal Albert Hall, as well as Upton Park football ground in London in front of 34,000 appreciative West Ham United fans. Long, meanwhile, has been described by The Daily Mail as "an uncannily convincing Sammy Davis Jr".
HBO's 1998 TV film drama The Rat Pack explored the original tight-knit unit's highs and lows, its triumphs and its dark side. There was a lot of politics behind the music, and the film explores Sinatra's knotty relationship with John F Kennedy, the controversy surrounding Davis Jr's interracial marriage with Swedish-born actress May Britt, and plenty more besides.
Such details only increase the potency of The Rat Pack's music, which was often an incredibly joyous thing despite all the background tensions. That's perhaps what you should hold onto this week when Triffitt, Adams and Long perform such classics as Come Fly with Me, That's Amore, and New York, New York.
The Definitive Rat Pack is at the Dubai Opera on Tuesday and Wednesday. Tickets cost from Dh175. For more information, visit www.dubaiopera.com