“It took me a long, long time to learn what I now know, and I don’t want that to die with me.”
—Frank Sinatra

Pundits often speculate why the Rat Pack remains so deeply embedded in popular culture.

Some reckon it was because the heart of the Pack, the holy trinity of Frank Sinatra, Dean Martin, and Sammy Davis Jr., were peaking in their respective careers precisely when they forged their fateful union. Others claim their rise hinged upon the testosterone-fueled reaction of the fading Macho American Male against the encroaching, decidedly un-macho hippie revolution. Yet others believe it was the diabolical work of vast media conspiracy—the newspapers fed on scandal then, as now, and the Pack gave them all they could stand and more.

Then there are those, myself included, who believe the well is much deeper than that. That the Rat Pack wasn’t just a gang of hard-drinking, easy-loving, high-rolling celebrities who happened along at the right time, but also something much bigger and much more difficult to define—an idea, an ethos, a subconscious creed whose roots extend all the way back to ancient Greece. The Rat Pack was the primal embodiment of the notion that we are not put on this earth to toil until death, but rather that we are here to swing.

Admittedly, their timing couldn’t have been more perfect. The conformist 50’s were colliding headlong into the gooey flower-power movement, and red-blooded Americans were at a loss as to how they were supposed to behave. They were desperate for leadership and suddenly a group of very confident cats climbed up on stage in a small desert town in Nevada to deliver a soused sermon of sheer unadulterated fun. And the world sat up and took notice.

It was January 1960 and they called it the Summit at the Sands. There would be other Summits later, but this was the opening shot of the Swinging Revolution, the party that was heard around the world. After a few straight songs, the show would devolve into something best described as a very public stag party. Songs were perpetually interrupted by wisecracks, political correctness was made a pariah, the sacred audience was cajoled and rousted, the performers openly drank deep from a bar centered on stage like a sacrificial altar. Much of the act was ad-libbed and riddled with inside jokes, and the audience—and the army of press that had gathered—suspected the performers were having more fun than those they were supposed to be entertaining. And they were right.

When they drank the whole swinging world drank with them and drank them in, taking cues as to what was square and what was a gas. Their waves of joy rippled around the globe as they staked out an island of cool in a confused cultural landscape. And, what’s more, they made it look easy.

Even now, decades after their heyday, the ripples are still spreading. Catch the wave, baby.

From funerals come flowers.
It was only after Ava Gardner shoved him into a black sea of despair that Frank was able to transform from a washed-up bobbysox warbler into the undisputed master of the boozy saloon ballad. Dean’s acrimonious (and most thought career-ending) break with Jerry Lewis allowed Dean to step out of the shadow of playing straight-man and into the light of master entertainer of all trades. The traffic accident that cost Sammy an eye lent him a fresh perspective on life (literally and figuratively) that gave him his final boost into super stardom. They’d all been to bombsville and they knew there was always something in the rubble worth taking with them.

Always act like you know what you’re doing.
Even if you don’t. Especially if you don’t. “We ain’t figured out what the hell we do up here,” Frank admitted onstage at the Summit, but by sheer force of gall they not only pulled it off, they made their off-the-cuff goofing around seem like a cool new way of doing things.

Work hard, but make it look easy.
Never let them see you sweat. Swagger beneath the spine-crushing yoke. Never let it appear your limits are being tested because, as Sammy pointed out, once the bastards know your limits you stop being larger than life and start being about the size of an average schmuck.

You get the kind of friends you deserve.
Frank learned that the hard way. During his first rise to the top he behaved very callously, willing to cut throat if it meant a step up the ladder. When he eventually fell off that ladder, very few hands reached out to catch him. During his second climb up, boosted by his Oscar-winning performance in From Here to Eternity, he was not only careful not to step on any fingers, he pulled up a lot of cats with him. His reward? The Rat Pack, baby.

Anytime is the right time for a party.
“Let’s start the action!” was Frank’s eternal battle cry. The Pack didn’t believe in down time, any possible moment was fertile soil for a wing-ding. “I may run for the office of president,” said Frank. “I’ll have a slogan on billboards all over the country: ‘Gimme a bottle and a glass and I’ll get America off its ass.’”

Drink like a man.
Wine was fine with dinner, beer was great for watching a baseball game, but it was hard liquor that powered the Pack. Jack rocks (Frank called it gasoline) was the primary fuel, supplemented with dry martinis and scotch.

There’s always a higher peak.
No matter how high you’ve climbed, no matter how many accolades lay at your feet, you should always be packing for the next expedition. Resting on your laurels is akin to greasing the rails of a sled balanced precipitously on a long, steep slope that goes nowhere but down. Trade in those comfortable slippers for a grappling hook. At different points in their careers each of the Pack had the opportunity to cash in his chips and say, “Man, that was one wild, swinging ride.” Instead they informed the dealer, “Sling ‘em, baby, I’m feeling lucky.”

Broads come and go but pallies are forever.
Romantic love has it’s place, but abandoning your pals for your current fling was akin to selling the ranch to go play a bit part in an Off Broadway western. An army of women marched through the Pack’s circle, they even married some of them, but the circle remained unbroken.

To be a good leader sometimes you have to be a bad man.
Nobody truly respects a thoroughly nice guy. Every great leader has a mean streak and Frank certainly had his. Glad-handing might earn you good will, but respect won’t follow unless they understand that hand knows how to ball into a fist. Frank could be the most giving, generous, and kindest pal in the world, but his clan understood that if you crossed him you’d better know how to duck.

When in doubt, swing.
In both senses of the verb. The Pack were firm adherents of the idea that there are few situations a good right hook or wild party won’t make more interesting.

Learn to take a punch.
Punches come in all shapes and from all directions: emotional, vocational and, yes, physical. Somewhere along the line it became standard behavior to admit your hurt, to cry over your pain, to bemoan the meanies who would do such a terrible thing, and finally to solicit hugs to make the hurt go away. The Rat Pack had a whole different idea. They understood that anyone who steps into the ring of a life worth living is going to get hit. A lot. And when you did, you didn’t run to your corner and weep, you rolled with it and angled for a vicious counter-punch.

Never sweat the small stuff.
The Pack lived within the big picture, they understood that if you were reaching for the stars it didn’t matter if your shoes were untied. Today’s troubles became tomorrow’s punchline. Case in point: When Sammy became suicidally depressed about losing his eye, Frank outfitted the rest of the Pack with matching eye-patches. Sammy cast aside self-pity and got on with his life.

Only take a shot at a pal when he’s in sight.
Trading barbs with pallies is a very important part of the male experience, but repeating the same insults when they’re not around is forbidden. Case in point: Sammy would trade the most insulting of wisecracks with Frank and Dean on stage, but when he took a shot at Frank during a radio interview, the Leader wouldn’t talk to him for two months. Sammy never made that mistake again.

Money does no good sitting in your pocket.
“You gotta spend it,” Frank said. “Move it around.” The Pack knew you earned a lot more interest spreading it thick (the recipients of their legendary largess were especially interested) than letting it sit in a bank. Whaddya angling for, pal, a solid gold coffin?

A lady ain’t a tramp.
A paradox, isn’t it? They called them broads on stage and in each other’s company, and Lord knows they womanized, yet they were very nearly Victorian in manner the rest of the time. Not only did they go for the sending-flowers, opening-the-door, helping-her-into-her-coat routine, they were also more than willing to defend a lady’s honor with fisticuffs. “I may sound old fashioned,” Frank said, “but I think all women should be treated as I’d want my wife, daughters and granddaughters treated.”

There’ll be plenty of time to sleep when you’re dead.
Some broads, as Frank liked to say, look better from the rear, and he felt the same way about the dawn. Throughout his life Frank waged a very personal war against sleep, he hated the very idea of it, he considered it a miniature form of death. It was when the action stopped, when the pallies staggered home, that dark thoughts started seeping in. Avoid it as much as possible.

Never apologize for your pals.
Sinatra mixed with mobsters, Dean associated with that thug Sinatra, and Sammy, for crissakes, palled around with Anton LaVey, the founder of the Church of Satan. They, for whatever reasons, saw something in them worth bonding to and never felt the need to explain why. Hey, they may be fuck-ups, criminals and reprobates, but they're your fuck-ups, criminals and reprobates.

Never rat on a rat.
Bogart, the original Alpha Rat, established that phrase as the gang’s motto and Frank enshrined it. “Pray silence,” was the Pack’s byword, the idea being, we’re all in this shady enterprise together, so who’s going to point fingers? Leave that to the press.

Make the most of your weaknesses.
Frank’s lack of classical training lent him the audacity to experiment with the form until he ended up creating a whole new way of singing. Dean’s ingrained misanthropy allowed him to cut the ties that would have bound him to a single genre of entertainment. You would have thought the entrenched prejudices of the day would have prevented a short, one-eyed, jewish, black man from rising to the top of the entertainment world, but Sammy used the stark spotlight of controversy to showcase his monumental talents. Noted Sammy: “Fame comes with its own standard. A guy who twitches his lips is just another guy with a lip twitch—unless he’s Humphrey Bogart.”

Nobody owes you a good time.
Except you. If you find the company you keep boring, maybe it’s because you’re putting them to sleep. If no one’s ring-a-ding-dinging the bell, get off your butt and do it yourself. It didn’t matter if they were stuck shooting a movie in a small Ohio town or the middle of a Utah desert, the Pack always brought the party with them.

Once you stop moving, you start dying.
Just like sharks. Frank considered impatience a virtue, fully understanding that lying in a rut is an invitation for someone to start shoveling dirt on you. When recording an album, Frank would tell the conductors, “Let’s keep it moving please, because if it bogs down, it’s deadly.” Inertia, he knew, is the death of creativity.

If you can’t do it with class, it isn’t worth doing.
That goes for drinking at a bar, taking a broad out on a date, throwing a party or walking into a room. What exactly is class? It’s the details. Tip like a king and deliver it like a secret. Formal attire but never overstated (Sammy sometimes bent this rule). Never let a pallie wonder where his next drink is coming from. Never yawn in front of a lady and always be quick to light up her smoke.

Better a proud thief than a humble beggar.
Frank and Dean stole from Crosby, Sammy stole from Frank, and the whole world stole from the lot of them. They never asked for permission and they never made any bones about it. They took what it was, made it better and passed it along.

Work to live, not the other way around.
“We’re not setting out to make Hamlet or Gone with the Wind,” Frank asserted in the midst of shooting Ocean’s Eleven. “The idea is to hang out together, find fun with broads, and have a great time.” During the shoot they would drink ‘til dawn, pass out, show up fantastically late on the set, start drinking again, execute each scene in one take, booze it up on stage at the Copa, then, finally, another date with the dawn. “The satisfaction I get out of working with these two bums,” Dino would say, “is that we have more laughs than the audience.”

Rules are for suckers.
“When your opponent’s sittin’ there holdin’ all the aces, there’s only one thing to do: Kick over the table,” advised Dino. Fences are for sheep and the Rat Pack soared above them like eagles. How will you ever know if the rules are even real until you give them a good kick?

Loosen up.
A lot of us should get those words tattooed across our knuckles, as a reminder we’re taking things too seriously. A light heart is the grease that makes uncomfortable situations slide right on by. Frank said it: “If you ain’t loose, you can’t swing.”

Regrets are a dangerous rearview mirror.
Spend too much time staring into that ugly little reflection and you lose sight of the road ahead. Regrets? The Pack had a few, but apparently too few to mention in their collected interviews. Best to just twist that mirror until your gorgeous mug is smiling right back at you. Now, isn’t that a better view?

Love the man in the mirror, because he’s the best pal you got.
“The only person who can hurt you is you,” Frank said. So treat him right, treat him with respect, and most of all, show him a good time. He’ll pay you back in spades.

The world breaks everyone, and those who break sometimes end up stronger in the broken places.
Hemingway preached it and the Pack were true believers. Frank’s post-Ava crackup, Sammy’s automobile crash, and Dean’s multiple divorces all made them more resilient, more eager to win, more willing to lay it on the line. Once bitten, twice bold.

You will know a true pal at first sight.
“You bypass the acquaintanceship stage immediately,” Frank explained. “Either your currents are different and the chemistry isn’t there or else you’re hooked and you’re a friend immediately and in most cases permanently.” Though their personalities were miles apart, Frank, Dean and Sammy hit it off right from the start, and over time they found enough common ground to build an unbreakable union.

Better two pals than a two hundred acquaintances.
Politicians, princes and bigwigs of every stripe vied for a place in their circle and were roundly rejected. Frank, Sammy and Dean understood every human being has only so much emotional energy to pour out and you could either give a crowd a small taste or get a couple pallies loaded. Which sounds like a better time?

Take care of the little guy.
They’d insult powerful politicians, punch out career-mangling newspaper columnists and pick fights with fellow celebrities, but they always took care of the guys who mixed their drinks, dealt their cards and carried their bags. They’d all worn those shoes and knew exactly how they fit.

A man without enemies is a man without character.
Let’s face it, if you stand up for anything, and I mean anything, someone is going hate you. Even saints like Lincoln and Gandhi got whacked. The Rat Pack, the original players, certainly had more than their share of player-haters. They shrugged it off, they knew it was part of the gig. Frank’s favorite toast? “Here’s to the confusion of our enemies!”

Women are, and shall forever remain, a mystery.
Said Frank: “I’m supposed to have a Ph.D. on the subject of women. But the truth is I’ve flunked more often than not. I’m very fond of women; I admire them. But, like all men, I don’t understand them.” And if the Chairman of the Board couldn’t figure them out, what chance do we mortals have?

Live in the now.
The past was where you screwed up and the future is where you die. The now is where you swing. “You only live once,” Frank noted, adding, “and the way I live, once is enough.”—Frank Rich