Frank Sinatra and the Rat Pack: The Ultimate #SquadGoals

No term dominated 2015 quite like ‘Squad Goals.’ Whether it was a photo of Taylor Swift hanging out with her famous friends or a picture of a raccoon and an alligator in Florida, the term hit the lexicon hard and it was everywhere. I like to call it a “squad-renaissance” as the term originally hit the pulse of pop culture during the days of ’90s hip-hop thanks to groups like Hit Squad and Def Squad. But for every photo posted on Instagram or Twitter celebrating friendship or the “wish you were one of us” mentality of exclusivity in 2015, all were far inferior to the truest definition of cool: the Rat Pack.


When Frank Sinatra paired up with Dean Martin, Sammy Davis Jr., Peter Lawford, and Joey Bishop, a new era of machismo, style, and debauchery was born and has continued to have an effect on both men and women for decades. If you think these men are overshadowed in the year 2015, think again. You can find that iconic photograph of the boys from the original Ocean’s 11 by a pool table in pizza shops, bars, and even college dorm rooms. Artists from Jay-Z to Kanye West have referenced the Rat Pack in song lyrics. Ocean’s 11 was remade and turned into a successful film trilogy starring George Clooney, Brad Pitt, and Matt Damon. Jack Daniels, a favorite of the squad, released a special whiskey in honor of Frank Sinatra’s centennial as a nod to the days when the liquor flowed freely as the Rat Pack dominated the Las Vegas strip.

If you weren’t around at the time, it may be difficult to grasp the level of fame the Rat Pack had in the swingin’ 60’s because the era was without social media but these men didn’t need it. All of them were established stars before getting together so when they did, it was dynamite. Like Taylor Swift, the biggest stars of the day were seen partying with the pack. If you were part of this “in crowd,” you were somebody. The rich, famous, and the infamous were all seen with Frank and his men even President John F. Kennedy. Peter Lawford was married to Kennedy’s sister, Patricia. Frank Sinatra would be a major player in Kennedy’s election campaign creating a modified version of his hit song, “High Hopes“, and working closely with Lawford and others to organize the President’s inauguration.

But Frank Sinatra didn’t start the original Rat Pack. It actually began with Humphrey Bogart in the 1940’s up until his death in 1957. Sinatra was a neighbor of Bogarts and became part of his circle of friends. The moniker, ‘Rat Pack’, is said to be coined by Bogart’s wife, Lauren Bacall. According to legend, Bacall saw Bogart and his drunken group of friends and told them they looked like a ‘rat pack.’


Bogart’s rat pack included Sinatra, Judy Garland, and David Niven.

Sometime after Bogart’s death, Sinatra carried on the torch assembling his buddies for late-night shenanigans that would turn into a Las Vegas act. Sinatra and Dean Martin became fixtures in Las Vegas in 1959 performing separately and then making cameos in each other’s shows. But Martin wasn’t strutting down a stage as an accessory ala Taylor Swift’s model friends when she performed ‘Style’ during her concerts. He would sing some songs both solo and with Sinatra and crack some jokes. His ‘guesting’ in Sinatra’s acts show the importance of collaboration to a squad, something that’s been happening between artists for years. Along the way the act expanded to include Sammy Davis Jr., Peter Lawford, and Joey Bishop.


The Rat Pack’s Vegas shows were a song, dance, and comedy act. Their schtick was about being the bad boys and the public ate it up. They performed hundreds of shows during their reign on the strip bringing in countless tourists including many wealthy gamblers who would pour money into Vegas as freely as the Rat Pack drank onstage. No show was the same. A lot was improvised and there were many special guests including a young Johnny Carson who would often serve as the emcee. While it appeared the men were drunk onstage, many say apple juice was in Dean Martin’s glass, not liquor, and Joey Bishop maintains it was all part of the act. In a 1998 interview Bishop said, “I never saw Frank, Dean, Sammy or Peter drunk during performances. That was only a gag! And do you believe these guys had to chase broads? They had to chase ’em away.”

The Rat Pack was an economic boom for Vegas, essentially revitalizing the strip. They reign was so supreme that whatever Sinatra said went. (Which could also be contributed to the power his mob friends had in the city as well but that’s another story) Sinatra’s power is even attributed to desegregating the strip. Due to segregation, Sammy Davis Jr. and other artists of color had to stay at black motels far away from the venues they performed in. Sinatra wouldn’t have that. He refused to perform in segregated hotels and casinos and other artists followed suit. He expressed his disgust in an interview with Walter Cronkite saying, “I found that going through the United States, there was a lot of it, especially in the south. It’s vile. It’s the most indecent way to live. It’s wrong.” As the popularity of the Rat Pack grew, hotels and casinos eventually abandoned their segregation policies. That’s how powerful he was.

As the act grew so did their stage. Peter Lawford bought the rights to the comedy caper, Ocean’s 11, and commissioned the heist picture to Sinatra as a vehicle for the pack on film. The film would use Vegas as their playground yet again but would show the world who this Rat Pack was that was taking over Vegas. After shooting the film during the day, the boys would perform their Vegas shows at night. But the making of this film wasn’t an all out party. Henry Silva, who portrays Roger in the film, stated that the Rat Pack was extremely disciplined while making the film with Frank and Peter making key decisions during its production. Ocean’s 11 captures the essence of the Rat Pack’s cool but more importantly the audience feels the camaraderie these men shared. It is a fun film to watch. Sinatra was very proud of the film and would often screen it for family and friends at his home. Two more Rat Pack films, Sergeants 3 and Robin and the Seven Hoods, would follow.

“The success of the Rat Pack or the Clan was due to the camaraderie, the three guys who work together and kid each other and love each other,” Sammy Davis Jr.

I’ll admit the remake of Ocean’s 11 is a superior film storytelling wise, however, the original is a snapshot of a group of men we will probably never see the likes of again. That’s where the remake fails. The Rat Pack wasn’t manufactured like the pluck casting of Clooney’s film, the relationships between these men were genuine and that’s why we still talk about them today. America wasn’t hardened by the cynicism the later years of the 60’s would bring, the Rat Pack represented the energy and excitement of the Kennedy era.


The ‘my way’ attitude that is such a part of the Sinatra mystique and also present in the Rat Pack is what makes them so appealing. Sinatra always rebelled against the establishment. The Rat Pack’s lifestyle was a reaction to the suburbia of the Eisenhower era much like the beatnik generation that was forming during this time (Jack Kerouac’s On The Road was published in 1957, the year Humphrey Bogart passed). Yet their methods couldn’t be any more different. The Rat Pack enjoyed the luxuries of penthouse suites mingling with other high rollers and “broads.” The Beats rejected materialism.

When asked if he contributed to the demoralization of America by Cronkite, Sinatra replied, “I don’t believe so. What I do with my private life having been divorced, I don’t think that much of the demoralization of a nation.” The Rat Pack’s mantra nonconformity is something  we all yearn for at some point in our lives. These men cared about only one thing: having a good time and boy, did they ever.

Not only did people want to act like the Rat Pack, they also wanted to dress like them. The skinny ties, pocket squares, and well tailored suits you see them wearing were symbols of that good life. It was the popular style at the time and the skinny tie makes a comeback every year at weddings, office holiday parties, and every event where people end up labeling themselves “classy.” Popular culture has never abandoned  the ‘Sinatra/Rat Pack’ aesthetic. It appears every year, just look at Justin Timberlake.


When he came out with the single “Suit and Tie” with Jay-Z off of his 2013 album, The 20/20 Experience, he went full on Frank Sinatra accompanied by a band behind him and even incorporated jokes into his act. The Rat Pack #SquadGoal was back this time as Justin Timberlake and Jay-Z. Jay-Z was even tapping into his inner Sinatra before Timberlake in his song, ‘Empire State of Mind’ where he declared himself the new Sinatra. The aesthetic goes beyond music. Both the Rat Pack’s style and masculine squad bonding is also present onscreen in films like GoodfellasReservoir Dogs, and Swingers. The thing is, the Rat Pack #SquadGoal has never left. It’s everywhere. When someone drinks Jack Daniels or an old fashioned, wears a skinny tie or a fedora, they are subconsciously entranced by the Rat Pack because of what they represented. The Rat Pack has become so synonymous with a lifestyle and ingrained in popular culture that we don’t even realize we’re thinking about. The Rat Pack made you want to live well and enjoy life. Unlike the masculinity of James Bond, the Rat Pack weren’t threatening, they were inviting and made you feel like if you went to Vegas, you got an invite to hang out with them even if their show was sold out. They defined cool and no one has been able to modify it since.

This post was a contribution to the Frank Sinatra Centennial Blogathon hosted by The Vintage Cameo and the Movie Classics blog.


5 thoughts on “Frank Sinatra and the Rat Pack: The Ultimate #SquadGoals

  1. thevintagecameo says:

    I love this post so much! Great analysis of the social/political factors that led to the Rat Pack vibe… plus all the photos, which are just so damn cool! I think I finally understand #squadgoals now—and it’s the Rat Pack!

  2. says:

    Wow, what a well-written article, congratulations! I agree that the Rat Pack is the ultimate Squad Goal. Imagine how much fun they had together? I also loved how you analyzed the long influence the Pack has had until today.
    Don’t forget to read my contribution to the blogathon! 🙂

  3. Judy says:

    This piece has made me realise how little I really knew about the Rat Pack, despite being a fan of Sinatra and having seen a couple of Rat Pack tribute shows! Thanks so much for taking part in the blogathon, and putting together all this fascinating information and analysis.

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s