5 Reasons Frank Sinatra Is Cooler Than All Of Us

On December 12, 1915, a baby boy was born in an apartment in Hoboken, New Jersey. Little did anyone know that that wailing little tyke would grow up to be one of the longest-lasting musical sensations in the history of America: Frank Sinatra. Now, a century later, the world celebrates Frank Sinatra’s 100th birthday, most notably with an All-Star Grammy Concert featuring Tony Bennett, Usher, and Adam Levine that aired on CBS on December 6.

With a swagger that remains unmatched by any other musician to this day, Sinatra defined what it meant to be cool for generation after generation. Even if you’re not an overwhelming fan of his music or status as a cultural icon, you can’t deny that the man possessed a certain “je ne sais quoi” that puts even the most self-assured among us to shame.

What was it about Sinatra that made him unquestionably cooler than all of us losers combined? Here are five reasons that the Sultan of Swoon is still the coolest cat ever.

1. He made formal wear an everyday occasion

Keystone/Getty Images
Keystone/Getty Images

Can you even think of a time when he wasn’t wearing a suit? Obviously, he had to take it off for things like showering or sex, but honestly I’m not even sure he did that. Who among us, regardless of gender, could even think about pulling off that kind of dedication to formal wear without looking like the biggest jerk in the world? Think of the ire we aim at people who try to pull off a fedora (which, don’t get me wrong, looks ridiculous 90% of the time). Can you imagine how your friends would respond if you suddenly decided to wear a tux everyday? It would probably go something like, “Who do you think you are, Frank Sinatra?” I’m sorry to say it, but you’re just not.

2. “He was a class act who also knew how to have fun

Hulton Archive/Getty Images
Hulton Archive/Getty Images

Most of us norms out here in Normalville have our paths very firmly defined. We may be either Goofus or Gallant, but never the twain shall meet. That was nonsense to Sinatra, whose persona was one half party boy and one half foreign dignitary. His voice and stage presence gave the audience liberty to have a good time, but ultimately it would be a dignified occasion. In fact, Sinatra’s whole life was like the last hour of a civilized dinner party: The guests are getting sloshy, but the cufflinks and pearls are in place.

3. Sinatra balanced hyper-bravado and maudlin vulnerability

Look, we all remember the swarthy manliness that defined Sinatra, who presumably reeked of whiskey, tobacco, and sex at literally all times. That part of the image has remained firmly entrenched in the psyches of men everywhere as an ideal of masculinity. What is potentially forgotten, however, is that the man didn’t just sing lively jazz standards about dancing cheek-to-cheek with dames. Half of his songs were melodramatic ballads about lost love with lyrics that could be dialogue from Grey’s Anatomy (listen to “My Way” and tell me Shonda Rhimes didn’t write that as a Meredith Grey monologue). Yet, despite his frequent forays into deep pits of vulnerability, no person in history has ever questioned the prowess of his masculinity.

4. Jack Daniels has a whole Sinatra-inspired select reserve line of whiskey

It’s not the cheap stuff either: The “Jack Daniels Sinatra Select Limited Edition” runs an astounding $200 (it’s like nobody told them they’re Jack Daniels). It’s a fitting tribute for Sinatra, who very well may be history’s most successful functional alcoholic. This is the man, after all, who once allegedly quipped that “alcohol may be man’s worst enemy … but the Bible says love your enemy.” How many of us nobodies have so successfully incorporated a drinking problem into the cornerstone of our brand that we’ll still be schilling liquor years after our death?

5. That voice

If you’re wondering why anyone could be interested in reading about the 100th birthday of a long-deceased singer, then look (nay, listen) no further than his voice. Whether Sinatra’s singing a plucky love song, a somber ballad, or a Disney standard, his dulcet tones continue to garner new fans. He was a consummate talent that remains unparalleled to this day, try though Josh Groban might. Don’t get me wrong: I’m sure you’re a really good accountant/actor/lawyer/blogger/basket weaver, but no one’s going to remember how good you were at that spreadsheet/monologue/deposition/Sinatra article/basket years after you’ve passed.

Follow James @doioweyoumoney on Twitter

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