Frank Sinatra's songs are timeless because they deal with the joys and pains every man lives through, no matter the decade he was born.

Love him or hate him, Frank Sinatra's fame is unquestionable. It's a credit to the man that, nearly 14 years after his death, the name Sinatra borders being synonymous with a swinging lifestyle, cocktails, and class. Sinatra ascended to a level of stardom high enough to have immortalized Gay Talese—because Talese wrote about him. The story itself is mesmerizing, yes. Talese is a masterful writer, yes. But it wouldn't have been Frank Sinatra Has a Cold without Frank Sinatra.

He was a caricature of himself—Sinatra sang, he danced, he drank, he cocked his hat, and he fooled around. But during that same time, the FBI surveyed him for decades under suspicions of mob connections. Sinatra's record of morality was far from immaculate. Had he behaved the same way in today's environment, his malfeasance would have been punishable by media crucifixion as opposed to a wave of the hand and all of the U.S. saying “Oh, Frank.”

Despite it all, there's something devilishly satisfying about empathizing with the things he so disarmingly sang about learning—without being forced to live through smoky, gin-drenched nightmares in the sands of Las Vegas ourselves. Regardless of who wrote the songs mentioned, Sinatra's way of telling us these stories is both uplifting and heartbreaking.

So, with that, let's get the show started with the lessons Frank Sinatra can teach us.

There Are Two Sides of Every Man

Sinatra was said to be happy only when he sang. And as a man who could sing a song like Send in the Clowns then Luck Be a Lady Tonight immediately after, he lived an accelerated life on stage. He relived the heartache Frank Sinatra isn't supposed to feel to play the role of a spotlit, solitary man devastated for two or three minutes. Then a finger-snapping, martini-drinking swinger as soon as the band cued up again.

Whether we play our roles through songs, women, jobs, or cities, a man is naturally dynamic. We're allowed to be card-playing, cocktail-sipping ruffians to a certain extent—but we're also susceptible to emotions so powerful they're debilitating.

For some strange reason, a paradox has emerged. Are we expected to be tough guys, chewing on toothpicks all night and strong-arming people? Or are we supposed to be the lone figure sitting at the bar, sipping on cheap whiskey while the world around us enjoys their time?

The answer is both. We're men, but we're human. And that's nothing to be ashamed of. Ol' Blue Eyes made a career out of it.

Remember the Past

In a Mad Men episode, Don Draper pulls the ultimate hedonist card, saying, “I'm living like there's no tomorrow … because there isn't one.” Sure. Great. When we're at the point our grocery lists consists of one entry—six bottles of Canadian Club whiskey—we might be inclined to say something like that.

But we can't avoid the past. It's something that clings onto us, even if only by thin strands of the cobwebs collecting on bad memories we tried to shake off years ago.

It Was a Very Good Year is quite the example of this. It's my dad's favorite song of Sinatra's and one of the first ones I've ever heard him sing. That particular tune exemplifies the way a man may measure his life. Women. Not in the derogatory “notch in the bedpost” kind of way. No, it's in a way that marks the epochs of a man's life: Hiding from the light on the village green. Perfumed hair that comes undone. Riding in limousines. It's sappy, sure. But it's also something that can just slide the proverbial tip of the knife into your side and reopen a years-old wound that spills fresh blood all over the floor.

The past is sobering and, when we're subject to distinct flavors of the same emotion we haven't felt in years, it can be devastatingly poignant. That being said, to live in the past or glorify ourselves for things we've done in the past would be a shame. And it'd be a horrible disappointment to our folks if we blew it.

…But Don't Live in It

If you're reading this, you're alive. And that's as good an excuse as any to work toward something. Indeed, taxes and death are the only certain things in life—but what that really does is give us a license to make sure all the variables surrounding them are filled with moments of necktie-wearing, Scotch-sipping greatness.

Enter the anthem of bohemianism: I'm Gonna Live Till I Die. Depending on what your definition of being a “devil” is, there will be a varying amount of hedonistic venture, but, when all's said and done, isn't our collective penultimate goal in life to have a long, storied Wikipedia page?

What it really comes down to is being that guy. Be the guy who isn't afraid to make a toast, to overdress, to admit when he's beat (but work for victory in everything else), to be friends with everyone. And while this isn't a call to go wild and do absolutely everything in excess. Not at all. What it is, though, is a reminder to live.

The song itself is like taking a shot of fire. At just shorter than two minutes, it's nearly impossible to not want more out of it. But in those two minutes, Sinatra's at his most brilliant. All of the lyrics are outstanding and a real kick to get a move on. Lay the blues low, make 'em stay low and never let them trial over your head. Shake it off, gentlemen. We've got work to do.

Love Will Wreck You

Come on, we all knew this one was coming. Sinatra's ability to belt out a tune about love is what makes him the bookends for anything and everything romantic.

What Sinatra does, time and time again, is remind us just how all-encompassing love is. Just take a look at his song catalog and you'll find dozens and dozens of tunes, each with a more pathetic title than the last. I'll Never Smile Again? All Alone? It's depressing just to see them.

Songs like Rain in My Heart—an epic, strings-driven tune—about the frenzied thoughts a man can have after his love leaves is immediately familiar to some. That lingering denial of the finality of your situation and the thought process attempting to reconstruct the sequence of how you got there in the first place is a singular experience. Whether we want it to or not, it takes precedence over so many of our thoughts, it becomes a situation of desperation, trying to find something to distract us for at least a little while.

But the tune that gets me, every single time, is Sinatra's take on Matt Dennis' Angel Eyes. It's a song that, unlike others that deliver an instant tone, erodes a man's feeling of security. You can surround yourself with people, you can see other women, you can have a drink, you can try to use logic to push away your feelings or convict yourself of being an idiot. It doesn't matter. Love will crush you, no question. It will beat you, drag you, asphyxiate you, break you, drown you, toast you, roll you up then smoke you. And if it didn't, it wasn't love.

But it can also be the most important risk a man can take.

Love Will Save You

My father told me a few years ago something I'll never forget. “You can only live half a live without a woman.” It sounds like a song Sinatra would sing.

Who wouldn't like to have the world on a string or feel a sense of warmth just thinking about how she looked tonight? I mean, for any deity's sake, Sinatra sang about how holding a hand or being kissed was comparable to be flown to the moon and playing among the stars.

What these songs do, though, is simplify a man's life. Love replaces the mundane, complicated parts of our days into obstacles to finish before we can enjoy the sunshine. Or the rain, snow, and sleet until we can be with the person we love.

That feeling of love is the ultimate redemption. We can finally not feel like we're owed anything. We revert back to the clean, simple lives of childhood, when everything was a wonder. With Sinatra, we ponder questions, in a genuine way, like how deep the ocean is. Or how high the sky is, how many roses are sprinkled with dew or how far the journey is from here to a star.

When it comes down to it, love makes life an enormous metaphor of tacky lines and everyday moments becoming suddenly more brilliant and beautiful. It'll make you snap your fingers, tap your toe and say to hell with everything else.

That's Life

The best part of it all, though, is the nice little bow all of this comes wrapped in.

Perhaps the last, most important lesson we can learn from Frank is what to expect. We'll be subject to everything the world can throw at us. We'll find ourselves in love, in despair and we'll cry and smile. We'll be puppets, paupers, pirates, poets, pawns and kings. We'll be up and down and over and out.

But, that's life. What else can we do but cock our hats back, straighten our ties and laugh?