A Breakfast of Champions: The Coolest Men of the 20th Century

It’s a question common to many a beauty pageant contestant. “If you could have a meal with any person from history, who would it be?” Well, we’re posing that question again here, only the answer this time isn’t going to be Abraham Lincoln.

It’s a question common to many a beauty pageant contestant.  “If you could have a meal with any person from history, who would it be?”  Well, we’re posing that question again here, only the answer this time isn’t going to be Abraham Lincoln.  Using the latest in objective scientific methods we have selected the four coolest people from the five most important parts of our culture from the last century: film, music, sports, literature, and kicking ass (and by “objective” I mean entirely subjective, and by scientific I mean we picked the ones we liked the most).

So, what is that you ask?  If I could break bread with any four people in history, who would they be?  How convenient of you to ask!

Steve McQueen

Hallmarks: The Great Escape, Bullitt, The Magnificent Seven

Not only is he the coolest guy of this bunch, he just may be the coolest guy in the history of Earth.  McQueen, along with James Dean, is the gold standard of the American anti-hero and he is the all time undisputed smoothest of all movie badasses.  He was even nicknamed “The King of Cool”!  From his untamable charm to his slick fashion sense McQueen was nothing short of a real life James Bond.  Just look at the names of some of the characters he played: The Cincinnati Kid, Thomas Crown, Nevada Smith, “Cooler King” Hilts, Doc McCoy, and of course Frank Bullitt.  There are few living men who wouldn’t trade their name for any one of those in a heartbeat.  Whether he is escaping from prison, protecting peasants from Mexican banditos, or flying down the streets of San Francisco in a “highland green” Mustang, face it; you are going to want to be Steve McQueen.

Lou Reed

Hallmarks: The Velvet Underground & Nico, The Velvet Underground, Transformer

Black sunglasses?  Check.  Black leather jacket?  Check.  Black motorcycle boots?  Check.  Natural born rebel?  Check.  The master of the “whatever” attitude, nothing about Lou Reed was ever done to be mainstream.  It doesn’t matter if he is singing about life’s simple pleasures, or heroin, or both, Reed has made his whole career by following no one but himself.  The original lead singer, guitarist, and principle songwriter for the Velvet Underground, he would later go on to create some very solid solo albums. One of the most influential of the influential songwriters of the late 60s, Reed is the only person to come out of Andy Warhol’s Factory to achieve any real long lasting success (or still be living).  In fact, Reed is the only member of this list to still be counted among us, which considering his extensive and well documented drug use, is a feat worth recognition all by itself.

Mickey Mantle

Hallmarks: 7 WS Championships, Most all time walk-off HRs, 1956 Seasons Stats

Mickey Mantle claimed to have never worked out a day in his life, was virtually a life long alcoholic, suffered from Osteomyelitis his entire career, and was still one of the greatest baseball players of all time and possibly the most beloved professional athlete in American history (what am I doing wrong?).  Playing for the biggest team in American sports, in the biggest city, Mantle’s “aw shucks” attitude, good looks, and penchant for hitting mammoth homeruns made him an instant fan favorite.   How mammoth, you ask? No one has ever hit a fair ball out of Yankee Stadium but Mickey Mantle hit a ball off the façade over the upper deck in right field (where the lights are now situated) twice!  He also has hit the two longest homeruns of any player in history at 643 ft. and 565 ft.  Both of these estimates are likely longer than the ball’s actual travel in flight but even with some discretion they are by far the longest official homerun measurements.  The greatest switch-hitter of all time and fastest man to ever play for the Yankees, Mantle played in a time when the public didn’t know or care to know about their heroes’ vices.  To this day, he is probably the most beloved Yankee in a long list of incredible athletes.  Forever the small town Oklahoma farm boy, Mickey Mantle truly embodied the spirit of an average Joe with supernatural ability and was every bit aware of the sensation he caused. On one occasion, Mantle was asked by a reporter how often he went up to the plate trying to hit a homerun.  Mantle answered; “Every time.”

Kurt Vonnegut Jr.

Hallmarks: Cat’s Cradle, Breakfast of Champions, Slaughterhouse-Five

The man who called smoking Pall Mall cigarettes “A classy way to commit suicide,” no one, not even the characters he has written, fit better into the term “anti-hero” than Kurt Vonnegut Jr.  Author of three of the greatest books in American literature, Vonnegut has an unforgettable, ingeniously simple style all his own. From his matter-of-fact tone in describing horrific violence or child-like insight into the darkest facets of human nature, Vonnegut has an undeniable knack for simplifying the complex and trivializing what we hold deathly serious.  Vonnegut, a WWII POW, abhorred violence of any sort and showed it in his works by filling them with crude, foolish, and deranged characters that recklessly destroy everything in their path. So it goes. This king of satire’s wry sense of humor wasn’t limited to his books, in a 2005 interview the then 83-year-old Vonnegut joked about suing Pall Mall for not killing him as their packaging “promised” to do. Vonnegut threw away society’s conventions and stood against all nationalist ideals in favor of a far greater, far reaching cause.  Kurt Vonnegut Jr. didn’t just love America, he loved humanity, and he had a hell of a way of showing it.

Bruce Lee

Hallmarks: Enter the Dragon, Way of the Dragon, The Big Boss

You think Chuck Norris is a bad ass?  Well, Bruce Lee killed Chuck Norris.  To ignore the coolness of Bruce Lee is to deny the existence of cool altogether.  Pretty much anytime you see someone kick someone’s ass, you have Bruce Lee to thank for what you just witnessed.  Popularizing a completely foreign sport isn’t easy (just ask David Beckham) but Lee did just that with Martial Arts, and not just in America, but worldwide.  His movies, particularly Enter the Dragon, paved the way for every Martial Arts-based action movie since and Lee’s distinct fighting style is still paid homage regularly on screen.  Everything from MMA to the Tae Kwon Do academy in your home town have Bruce Lee to thank for being on this earth, and you had better recognize.

Kevin H. MacLean currently resides in Brooklyn, NY where he enjoys people watching, writing, and dominating all comers in four-square. You can keep tabs on him at his blog http://ratedwrong.com/.


  • Reply December 7, 2009


    Every time I see a ‘Coolest Men’ list, I know I’m going to see Steve McQueen. The guy is the epitome of a legend.

  • Reply December 7, 2009

    Keith Nelson

    Paul “Bear” Bryant. What is not cool about winning? No hollywood hype here. Unfiltered Chesterfields and Jack Black neat. A mans man.

  • Reply December 7, 2009

    Matt Licari

    Good article Kevin. But, I must say that your list is a bit “monochromatic” ( with the exception of Bruce Lee). How can you write an article about cool without including some prominent African-Americans? Black guys in American have created everything that “is” cool. What kind of sorry, sad, Bevear Clevear world would we be living in without the likes of Miles Davis (who literally Birthed Cool), Richard Roundtree, Robert Johnson, Richard Pryor, John Coltrane, Duke Ellington, Thelonious Monk, and Little Richard?

  • Reply December 7, 2009


    Hey matt, what can I say. I guess I’m racist.

    But seriously, if I was going to include a black person on this list it probably would have been Gordon Parks (photographer, author, director of Shaft). The music category was definitely the most difficult to pick, I tried to decide on someone that transcended their genre and had a lasting effect on things other than music (as well as me personally). Miles Davis has huge rep for being “cool” but I honestly never saw what the hype was about, Hendrix and Springsteen were the other choices to me. Richard Pryor is definitely cool but if I was going to include a comic it would have to be Lenny Bruce. He was doing Pryor’s act before Pyror was even out of grade school.

  • Reply December 7, 2009


    My list of ‘Coolest Men’ would linclude James Dean, Jimi Hendrix, Cary Grant, Hugh Grant, Gregory Peck, Clark Gable, Joe Perry, Keith Richards, Johnny Depp, and the coolest man who ever lived: Dean Martin.

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  • Reply December 26, 2009

    baatin ruler

    wow! not a single black dude, huh?

  • Reply February 11, 2010


    why does everything ,no matter what the subject is always have to break down to race . People are getting sick of hearing it . If you think you have it so bad , try going back to the 1920s or 30s .Now they had something to raise hell about .Do you think black guys back then would even care about this unimportent list .No they worried about real matters .

  • Reply June 19, 2010


    McQueen was great at LOTS of cool things, the man could race a car or motorcycle at international level, he could act with the best in Hollywood and he could street fight (a trained martial artist and an amazing athlete). He not only had all that but he had a very cool fashion sense, masculine looks and had an inner calm which made him appear very self confident, cool, cool and more cool. He did it tough growing up, made incredible income doing what he loved and had women drooling all over him. It’s every boys childhood dream, he had the whole package. Men wanted to be him and women wanted to be with him. Let us finish with one of his famous quotes “I live for myself and answer to nobody.” Cool.

  • Reply January 30, 2011


    what about hemmingway?

  • Reply December 3, 2012


    Ian Fleming?

  • Reply February 28, 2013


    I have to say I see a distinct lack of one man I expected to see at the number 1 spot: Jimi Hendrix. You don’t get much cooler than playing a guitar with your teeth while humping an amp.

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