11 Lessons Generation-Y Can Learn From The REAL Hunter S. Thompson

by Grant Goodwine

Who is Hunter S. Thompson?  Some of you might accurately refer to him as an insane outlaw journalist known for his avid drug abuse and reckless behavior.  Many of you know him best only by his alias, Raoul Duke, the rebel antihero in his legendary novel, Fear and Loathing In Las Vegas.  On the big screen, Johnny Depp portrays his character.

It turns out that Thompson’s public reputation hid the true man behind the beast that gave birth to Gonzo journalism. 
The general public is a bunch of Raoul Duke fans, and in the end, Hunter gave the public what they wanted.

Within these last few months, I've become friends with various people who were once well-acquainted, or longtime friends, with Thompson - the real Hunter S. Thompson.  These people knew the generous Southern gentleman who worked his ass off his entire life, while putting it all on the line to become a great writer.

Although he was born in 1937, Thompson’s journey to greatness has a lot to offer Generation-Y.  Luckily for us, he knew full well he was born to be a great writer and made carbon copies of every letter he ever wrote, anticipating compiling them into a book in the future, which would be called, ‘The Proud Highway.’ From this greatly inspiring read, as well as my discussions with his old friends and colleagues, here are the lessons Generation-Y can learn from Hunter S. Thompson:

1) Don't ever try to fit in.

Why make the effort to fit into a crowd? It’s a waste of your time and it’s a restriction on your true self. Stand out from the crowd, and let your freak flag fly.  Hunter was always an odd bird, who was both loved and hated for character. He was given an early honorable discharge from his service in the Air Force as a result of his lack of conformity.  Why be like everyone else? Why not aim to be much greater than the average, standard civilian?

2) Study the work of someone you admire.

When working at TIME magazine as a copy boy, Hunter hijacked one of the typewriters and copied F. Scott Fitzgerald's ‘The Great Gatsby’ and Ernest Hemingway's ‘A Farewell To Arms,’ both word-for-word, to get the rhythm and feel of how to write a great novel. I, too, have done this, but by trade, I am an illustrator, so I recreated Ralph Steadman and Terry Gilliam drawings to get a general feel of how to attack the paper. Anyone with a dream career looks up to someone and is greatly influenced by him or her. Do your research on success stories and see how it can help move you and better your trade.

3) Get angry.

Although kind and generous, Hunter S. Thompson was also an angry bastard; however, instead of turning destructive with it (well sometimes he was, thanks to guns and propane tanks), he channeled that anger into pure drive. It encouraged him to write, to become better and to push forward. Hunter often turned his anger into constructive outlets.  Out of all the lessons I've learned from Hunter, this one has by far been the most helpful for me.  When I get into an angry mood, I pour myself a glass of scotch and find the path to drawing, or writing, it out. When done, I either find myself feeling better, or on a roll with my writing and drawing.

4) Money is no excuse.

Once upon a time, Hunter was a sports editor for a newspaper in Jersey Shore, Pennsylvania.  At that time, he decided to take a co-worker's daughter on a date, and he used the said co-worker's truck to go on that date. With the help of underage drinking, Hunter drove that truck straight into a swamp.

To add insult to injury (since wrecking his co-worker’s truck and getting his underage daughter wasted wasn't enough), Hunter tried retrieving the truck and ripped the bumper off in the process.  Because of this incident, he hastily quit his job, packed up his car and moved to New York City with $115 to his name. 
Upon arriving to New York, Hunter found his job working for TIME magazine and was eventually fired for insubordination.

He then moved to Middletown, New York, with even less money in his pocket, to work for the town’s newspaper, where he was fired for breaking the candy machine and arguing with a local restaurant owner.  After that, Hunter stayed in Middletown for a short while, living on little money in a shack outside of the town.  Eventually, he relocated to Puerto Rico, until hitchhiking his way to California.  What I’m getting at is simply that you don't need all the money in the world to go where you want to go and do what you want to do. Just try to not burn bridges as Hunter did. Somehow, though, the dude made it all work out.

5) Don’t limit yourself to a certain crowd.

You can put Hunter in any scene. He ran with them all: artists, writers, intellectuals, politicians, bikers, hippies, beat poets, actors, businessmen, musicians and activists. Keep it interesting, dammit. Hanging out with one specific crowd, with one type of people, eventually gets boring and your personality will suffer for it. Diversify! You will come out a more well-rounded individual.

6) Keep good company.

Hunter was a popular fellow. In his later years, everybody wanted to spend a weekend at his property outside Woody Creek Colorado.  Eventually, Hunter became so popular within the entertainment industry that he would put potential employees through a test, usually involving scaring the crap out of them, to see if they were of the right background to work for his company.  He also did this for a personal laugh, but it was primarily a safety precaution to weed out the fakes and phonies who only wanted to be friends with a celebrity. Weed out the fakes and phonies in your inner circle.  Your life will be a lot more enjoyable and much less stressful.

7) Be civil, but take no sh*t.

The politician Hunter despised the most was Richard Nixon.  He wrote many horrible things about ‘ole tricky Dick; however, despite his hatred for the man, they once ended up sharing a limo to the airport.  Hunter was civil, Nixon was civil and they talked about football. On the other hand, when any one person gave him sh*t, Hunter would throw it back tenfold. Here's a piece of letter he wrote to the producer of ‘ The Rum Diary,’ while impatient regarding the slow production rate of the film:

"So there’s yr. f’cking Script & all you have to do now is act like a Professional & Pay him. What the hell do you think Making a Movie is all about? Nobody needs to hear any more of that Gibberish about your. New Mercedes & your. Ski Trips & how Hopelessly Broke the Shooting Gallery is…. If you’re that f’cking Poor you should get out of the Movie Business. It is no place for Amateurs & Dilletants who don’t want to do anything but “take lunch” & Waste serious people’s Time."

Hunter had fun with this letter.

Here’s a video of Warren Zevon reading the entire letter, with Hunter sitting next to him giggling.

8) Never give up; never settle.

This one’s pretty self-explanatory. Hunter worked hard to get to where he was, and yes, he was rejected countless times. But even when staring poverty in the face while under a pile of rejection letters, he never gave up. He kept writing. Hell, he finished writing ‘The Rum Diary’ when he was 25, in 1962.  The book wasn't published until 1998.

9) Find your voice.

Cocky young Hunter always said that he was going to be "the next F. Scott Fitzgerald."  Well, it turns out Hunter wasn't the most talented writer of fiction, but by complete accident in 1970, his immense talent revealed a new form of creative journalism that he discovered by mistake: Gonzo journalism. Gonzo journalism revolutionized the industry by throwing the writer into the story. And with Hunter's gruesome creativity and sense of humor, his work skyrocketed him to fame. Keep trying to do what you’re good at, or new things, from a different angle. Eventually, you’ll find your fit.

10) Cross the edge.

“The Edge… there is no honest way to explain it because the only people who really know where it is are the ones who have gone over. The others - the living - are those who pushed their control as far as they felt they could handle it, and then pulled back, or slowed down, or did whatever they had to when it came time to choose between Now and Later.” - HST

There are many ways to interpret this quote, but to me, I believe "the Edge" is the point of no return. No backup plans, no fallbacks or ways out.  It’s all or nothing from this point forward.
Ballsy as it may be, this is what many successful people have done to get to the top. They took off the safety harness and let the fear of failure propel them forward. Failure is not an option anymore; to fail is to die.

11) Don't take life so damn seriously.

From blowing up tractors with inflatable sex dolls, to speeding down mountain roads in his convertible, to shotgun golf, Hunter knew how to have a good time. His sense of humor may have been cruel, but his friends understood and went with it. He often called his good friend Ralph Steadman a "twisted filthy little pervert." He never meant anything of it. He was just having fun, and old Ralph threw it right back at him saying that his drawings were the only reasons Hunter's writing got noticed - just poking fun at each other.  He always surrounded himself with good friends, good liquor and some sh*t to blow up.

Hunter Stocton Thompson | July 18, 1937 - February 20, 2005

Rest in peace you brave, crazy bastard.