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10 Classic Male Icons Who Were Effortlessly Cool Yet Notoriously Flawed

Some people just have *it* and these men had it. Every woman wanted them and every man wanted to be them.

Never mind the occasional drug, alcohol, or spousal abuse.

Beware who you put on a pedestal.

    1. Kurt Cobain.

    One of the great musical minds of his generation, Kurt Cobain, and his newly-minted "grunge" band Nirvana, took the world by storm in the early 1990s. Alas, his fame was short-lived due to a descending spiral of drug abuse that ended with suicide. He was 27 years old.

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    2. Miles Davis.

    The famed jazz trumpeter Miles Davis once allegedly claimed to First Lady Nancy Reagan, right before he insulted her for doing nothing special in life other than sleep with the President of the United States (he used more colorful phrasing), that he changed the course of music "five or six times." Despite the course bravado, he was right about his musical influence. Davis bridged the bebop, cool jazz, modal, free jazz, and pop jazz eras with seemingly no effort, often leading the way. Unfortunately, along this remarkable journey, he also terribly abused heroin as well as every wife to whom he was married.

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    3. Frank Sinatra.

    Sinatra possessed a magic combination of a beautiful, suave voice, exquisite musical timing, and endearing good looks. These traits catapulted him to well-deserved international fame for over half a century. Other traits he possessed were a violent temper, an affinity for late-night alcohol abuse and gambling, and the occasional flirtation with organized crime.

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    4. Jimi Hendrix.

    Like Cobain, Hendrix burst onto the popular music scene at a young age and in an explosive fashion. His guitar playing was like nothing anyone ever heard, his albums were on the shelves of anyone under the age of 30, and his performance style was revolutionary. All while never being able to read a note of music. Unfortunately, also like Cobain, Hendrix never made it past age 27, as his legendary abuse of alcohol and drugs, which often sent him into violent rages, lead him to pass out and choke to death on his own vomit.

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    5. Steve McQueen.

    Steve McQueen was an actor with cool good looks and a penchant for playing parts that put him at odds with mainstream culture. He was the highest-paid actor in Hollywood for a time, and he lived the lifestyle to its fullest by famously racing cars and motorcycles. While his public persona was one of an enviable movie star, his private life was not as rich. According to one of his ex-wives, McQueen often enjoyed abusing cocaine...and her.

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    6. Joe Namath.

    Broadway Joe," as the great New York Jets quarterback came to be known, was the ultimate lady's man. And he was as smooth on the field as he was off of it. His rugged good looks and bravado made him a fan favorite, and their adoration paid off when he lead the underdog Jets to a win in Super Bowl III. Following his playing career, he tried his hand at acting and often found himself on the opposite side of Hollywood's most attractive actresses. Along with this idealistic life, Namath notoriously abused alcohol for decades before an embarrassing incident on national television in 2003 pushed him to finally quit.

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    7. Mick Jagger.

    Who doesn't know Mick Jagger? It seems implausible, but this middle-class white man born in the UK managed to take the world by storm with his band The Rolling Stones in the 60s by taking the rhythm and blues sound of African Americans and turning it into a worldwide rock and roll sensation. The band continues to perform 60 years after it began, but it hasn't all been sunshine and roses. Along the way, Jagger managed to dabble in all sorts of sins, including heroin abuse, acid, heroin, and alcohol, and reportedly enjoyed the company of the occasional prostitute.

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    8. Herbert von Karajan.

    Herbert von Karajan was perhaps the greatest conductor of the 21st century, which is a bold statement given his competition consisted of luminaries such as Leonard Bernstein and Arturo Toscanini, among others. The Austrian conductor's unorthodox interpretations of some of the great symphonies and operas in the western classical canon, notably Beethoven's symphonies, caused as much vitriol as it did adoration. He famously conducted with his eyes closed, yet his performances were flawless and the sounds he extracted from orchestras were remarkably beautiful. He also had an impossibly cool demeanor. Sadly, von Karajan had a dark side as well, as he held an adoration for the German Nazi party during the 1930s, with his membership helping to initially launch his career into stardom.

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    9. Jack Kerouac.

    Jack Kerouac's classic "On the Road" is required reading for any 20-something interested in wandering through this world in search of adventure. Along with his literary contemporaries Allen Ginsberg and William S. Burroughs, Kerouac was the unofficial leader of the Beat Movement of the post-war 1950s. Sadly, his lifelong abuse of alcohol and penchant for depressive episodes lead to cirrhosis, causing him an early death at age 47.

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    10. James Dean.

    For a very brief period in the mid-1950s, there was no one more famous on the planet than James Dean. His most famous film, "Rebel Without a Cause," could have been eponymously named after him. Dean embodied the persona of a cool, disenchanted, anti-establishment youth both on screen and off. However, he reportedly enjoyed engaging in sexual exploits with both men and women in order to build his Hollywood career. His short life came to an end at age 24 when he was speeding in his 1955 Porsche 550 and slammed into a vehicle that turned in front of him.

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