Song = "Alley Cat"
Sinatra's gang drew its members from the young, hip actors making it big in the movies in the 1950s.
Alongside Sinatra sat Sammy Davis Junior, Dean Martin, his co-star Jerry Lewis and Peter Lawford, and their drinking, womanising and gambling around California kept the gossip columns bubbling with the latest deeds.
Sinatra and the Pack summed up the archetypal American male - pre-Vietnam, pre-women's lib, pre-gay pride and pre-civil rights. It was a golden era for chasing the girls, drinking heavily and pushing bad behaviour to new limits.
Dubbed "Chairman of The Board" by fans, Sinatra was the incorrigible hero, and the more his gang played the club-lounge layabouts, the more the public loved it.
Sinatra was always in the news from the late 1940s. Headlines raged, from an assault on a columnist, tales of extra-marital affairs, accusations of Communist tendencies and allegedly socialising with mobsters such as Lucky Luciano.
Despite bust-ups that lasted decades, Sinatra admitted he lost his best friend when Dean Martin died on Christmas Day 1995.
He said at the time: "He was my brother. Not through blood but through choice."
Sinatra, who had seen all of his clan die ahead of him, was said to have been devastated by his death.
In the 1980s, the movie star camaraderie even sparked imitators, most notably the Brat Pack stars, including Rob Lowe, Charlie Sheen and Emilio Estevez.
But devotees of Sinatra and his fellow rebels would have viewed the modern-day version as a pale imitation of the original gang.