Frederick Nietzsche once said, “Without music, life would be a mistake.” I vibe that. Music can kickstart you in the morning and help you through the roughest Monday. It can make that workout just a little less painful, express your feelings, or set your mood. Who hasn’t daydreamed about tearing up a stage and playing their heart out in front of an adoring crowd?
Though the world’s seen distinct eras of popular music, I’m pretty partial to rock ‘n’ roll. Born and bred right here in the U.S.A. and imbued with the spirit of rebellion, I love our rock. Here, I present to you a list of the coolest cats who ever rocked all night, and the looks they inspired us with.
1. Frank Sinatra
Coolest Track: “My Way”
The Look: Gray suit, black fedora, and tie
Maybe your exposure to Sinatra might be limited to background music at a “grown up” party or an Italian restaurant. I call this olive-voiced crooner the proto-rock star. He’s hands down one of the most successful musicians in human history and one of our country’s very first megastars. He began his career as a band member, and over a tenure spanning the greater part of the 20th century, concluded as an icon. He also killed it as an actor, his screen prowess almost matching his musical success. A Colossus of Cool who did it all with style, cocktail in hand, he always swayed to his own beat.
Sure, he had his foibles, but his voice is as timeless and recognizable as his fashion sense. If you ever need to pass yourself off as a well-respected man-about-town, take a cue from Frank and top a tailored suit off with a fedora. Don’t worry if no one else is wearing one at the party; Frank wouldn’t have cared.
2. Elvis Presley
Coolest Track: “That’s Alright (Mama)”
The Look: Varsity jacket, black button-down with an untamed collar
Say what you want about the man, but the fact is he remains one of the most influential cultural icons this country has ever produced. It all started in 1953 when he walked into the offices of Sun Records to record so he could tell what he “sounded like.” His career charged ahead for the next 20 years through endless hits, cheesy flicks, and a late ’60s reinvention. Not so bad for a country boy who was considered “average” in school.
He may have lived at odds with himself, and he burned a little too bright and out too quick. Still, from the controversial hip shaking to the unapologetic pageantry, the man was an American rhythm master. He presented no shortage of iconic looks over the two decades of his career. I’m kind of partial to his outfit from the cover of his debut album: white suit, black shirt, and earnest love for the performance. He often took his cue from that unruly cadre of Brits and keep it black pretty often. All you need is a houndstooth blazer or a varsity jacket to emulate the man from Memphis.
3. Miles Davis
Coolest Track: “Freddie Freeloader”
The Look: Oxford not quite buttoned all the way, black slacks, maybe a jacket that’s bound to adorn the back of a chair
Miles Davis was a master. The man made an album called “The Birth of Cool,” and I don’t find it remotely boastful. Aside from creating what is often regarded as one of the best albums of all time in Kind of Blue he also redesigned music itself in the jarring, psychedelic-tinged Bitches Brew (with one of the coolest covers ever, to boot). Oh, and there’s the career that lasted nearly half a century. He was an innovator who had a hand in about every developmental shift the genre saw, and worked with just about everyone who was anyone. Trust me: jazz is cool. You will listen to jazz. Go listen to jazz. [Cough, cough]
The man had many iconic moments and the looks to accompany them, but let’s go with an Oxford button-down tucked in to a pair of black slacks, maybe a kerchief or a bare chest (depending how hot you intend on playing).
4. The Johnny Cash
Coolest Track: “Folsom Prison Blues”
The Look: Black suit, white shirt, no tie
The man’s look is as symbolic. I could simply reference “The Man in Black” and leave it at that. Rock star. Country troubadour. Legend. A man who was simultaneously a voice for the marginalized and a hard living honky-tonker. He blurs lines of taste, revered as much by hillbillies as hipsters. Playing shows for prisoners, championing young up-and-comers, and nurturing an ever-resurgent career for 60+ years, he deserves The in front of his name.
The look I’ll always remember is black suit, white shirt, lose the tie. Still good for a Saturday night outing or for playing some razor-steady rockabilly onstage in some music hall.
5. Bob Dylan
Coolest Track: “Subterranean Homesick Blues”
The Look: Wrinkled Oxford, striped sailor tee, acoustic guitar
Folk rambler and rock ‘n’ roll poet, Dylan was the vanguard for the ’60s folk movement. Eschewing college to vagabond up to NYC to visit his idol, Woody Guthrie (who was in the final stages of his life), this American icon cut his teeth in a high school cover band and then solo sessions at coffee shops. Taking cues from the folk pickers and blues belters who came before, he voiced with wit, humor, and sincerity the vibe of one of nation’s most cataclysmic eras. Then he went electric and blew the whole thing down. He also made it cool to wear sunglasses all the time, not answer to anyone, and reinvigorate your music career via constant experimentation, reevaluation, and a defiant refusal to be boxed in to people’s expectations. If that ain’t rock ‘n’ roll, what is? Oh, there’s also the fact that he’s been been making music for the better part of 60 years. Seriously, he’s almost as old as your grandparents, and he’s still knocking out cool albums.
I love almost all of his looks (not sold on the cowboy phase), but I’ve got to give it up to early Dylan. I’m thinking the cover of The Freewheelin’ Bob Dylan: a wrinkled Oxford matched with a sturdy pair of denim, some leather boots, a striped sailor tee, and finished with a brown suede jacket. Acceptable both for strolls through the Village with your best girl and your first solo gig at that basement club you begged your way into.
6. Mick Jagger
Coolest Track: “Sympathy for the Devil”
The Look: Black leather jacket, mouth tee
Aside from getting arrested fairly regularly, living the embodiment of rock ‘n’ roll rebellion, and staying together so long that I’m pretty convinced a deal was made with Old Scratch somewhere along the way, The Rolling Stones are a proper legacy. One of the greatest. They took rock ‘n’ roll and injected the blues and soul. They played it all twice as loud. I can only imagine that mop-top boyband was a little envious.
Mick’s onstage gyrations and antics must have made the old hip-shaker Elvis blush just a little. He’s had a lot of looks, but I’m going with the black leather jacket, iconic mouth tee, and don’t-give-a-$*#! attitude. No, wait, the open chest tee with leather pants? Hmmm…
7. Jimi Hendrix
Coolest Track: “If 6 Was 9”
The Look: Band leader jacket and hair that’s as wild and untamed as the man
We all know he did the definitive cover of “All Along the Watchtower,” and everyone has heard his distortion-saturated rendition of the American national anthem, but other than being part of the 27 Club, what do we really know of the man? He paid his dues playing backup for the likes of the Isley Brothers and Little Richard before he made it big on his own. Though his mainstream career lasted a mere four years, he is arguably one of the most influential musicians of the 20th century. His three studio albums are widely considered to be three of the greatest of all time, and he made guitar distortion and effects an art form. He was indisputably an instrumental maestro who brought rock to new, louder heights. He played for the likes of Paul McCartney, Pete Townsend, and Jeff Beck, and he even blew their minds. He also lit his guitar on fire and created one of the most badass moments in rock history. Okay, so I don’t exactly emulate the more psychedelic ’60s apparel myself, but what rock icon list would be complete without this wildman who changed the whole scene?
8. Joey Ramone
Coolest Track: “Rock ‘n’ Roll High School”
The Look: Black leather jacket, band tee, well-worn denim, sunglasses at night
Born as a rebuttal to corporate stadium rock—a petulant, permanently erect middle finger at the establishment (which we all know is the soul philosophy of rock ‘n’ roll)—punk rock proved that fast, loud, and simple was the antidote to the status quo. Of this era, there may be no more enduring legacy than that of the Ramones. Pumping out two to three minute tracks that play like infinitely catch renditions of Beach Boys songs on the wrong RPM setting, at the forefront was lead singer Joey Ramone. He was the kind of cool that hovers in the stratosphere: never quite attainable, or even understandable, but always admired. And the uniform for the revolution? A pair of denim that’s seen better days, a striped or band tee, and a leather biker jacket that proves that every man’s got a little outlaw in his heart. Finish it off with some Chucks, sunglasses you never take off, and a general malaise directed at all authority.
9. David Bowie
Coolest Track: “Life on Mars?”
The Look: Black vest, white shirt, no tie
When you talk Bowie, you’re talking iconoclast, because the man was able to capture the zeitgeist through reinvention enough times to make the Phoenix look like a slacker. Working for about 50 years almost until the day he died, the man made his mark in music, film, and fashion. Chased by women, envied by men, and befuddled over by squares, the man was truly an icon. Merging visual art and pure flair with rock, pop, and electronica, he was a chameleon of cool and a trailblazer for the ages.
Though he sported many looks, we’ll take white shirt, black vest, no… Sorry, got distracted by no shirt open leather jacket Bowie: no tie. We’ll forget about “Dancing in the Street” and give you our eternal salute, Starman. Pegging down Bowie’s coolest look is a pretty lofty task, so let’s just go with one we all love. It’s both a Saturday night favorite and an album cover essential.
10. Bruce Springsteen
Coolest Track: “The River”
The Look: All about denim
Listening to The Boss might best parallel going to a Labor Day BBQ at Abe Lincoln’s house and kicking back beers with Uncle Sam while George Washington grills out, Betsy Ross gets a tan in her American flag one-piece, and a few eagles fly overhead. Melding folk, blues, and country, this gravel voiced Jersey boy might be American rock ‘n’ roll personified. Honestly, I’d vote for him for President; there’s no disputing he was born in the U.S.A., I’d definitely get a beer with him, and I feel like he’d actually listen to my problems and then write cathartic songs about them. Springsteen 2024!!!
Aside from going strong since the 1970s, he’s also one of the best selling artists of all time, he has consistently used the spotlight to be a voice for change, he’s racked up Grammys and even an Academy Award, oh—and blew off millions of dollars from Chrysler, who wanted to use his song in a commercial. The Boss indeed. His look has changed a little bit over the years, but like his work ethic and commitment to the E Street Band, one thing has been consistent: denim. Further evidence that it’s un-American for a man not to have at least one sturdy pair of denim in the repertoire. The Boss hast matched it with tees, a denim jacket, and a button-down with a tie and vest. I support these decisions.
Reality Changing Observations:
1. What defines a rock icon?
2. Who are your pop culture heroes, and why?
3. What music will you pass on to your kids, grandkids, students, nephews and nieces, etc.? What stories will you tell?
