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The Heroism of the Happiest Homeless Man Part#1

Posted on | July 28, 2010 | 1 Comment

In this world, there are those fortunate enough to be born with a silver spoon lovingly inserted between their tit trap teeth.  Our hero was born in a trashcan and always treasured every moment in his very strange life.

On the night he was born, as stars sparkled in the distance, as motel six customers paid their rental fees and had their secret rendezvous, a child with big brown eyes and chipped teeth opened his eyes for his first glance at the people who brought him into this world—as they quickly and quietly made their escape from his life.

Listen to his mother and father frantically scramble to get away from the garbage can where they have placed the baby to begin his fabulously happy existence.  On her head rests a crown declaring her the very belle of the high-school prom. She beamed, glad to be away from the life she never chose to lead.  Her boyfriend, head quarterback of the football team, offered her a smoke.

She gave him a sweet smile and lit up.

“Thanks, quitting smoking has been the toughest thing I have ever had to do,” she says, before taking a greedy inhale from his delicious Canadian classic cigarettes, smearing her ruby red lipstick on the tip.

He kissed her hand and they get in their Honda Accord and make their way back to Prom, ready for him to go to university and become a doctor and for her to one day be a runway model.

Inside the garbage can, through a veritable cloak of filth, the child giggles until he can barely breathe.  Never has there been a child as glad to be alive and a result so nearly dead.  See he would have lived his whole life laughing if not for a visit from his future best friend.

Monkey slips into the room like lightning let out of the hands of Zeus. This Monkey is not a monkey but a cat.  This Monkey is an indulged pussy, fur as orange as a sunrise, eyes as blue as BB King’s music.  The cat was used to eating scraps left behind by hotel guests and letting the dirty guests pet him because he too had no one to give him attention.

Thankfully he recognized the laughing child to be more than a scrap left behind by the previous occupants of the room.  Monkey was extremely repulsed by the wreckage that comes with human birth and was almost too squeamish to aid the laughing babe. Then the babe’s laughter sent a spiral of red fluid into Monkey’s perfect soft organeish red hair.

“What do ya do that for you, you lug?” asked Monkey, in a quick series of indecipherable purring sounds.  He followed this statement by bashing his paw into the baby’s back.

The babe promptly breathed in and saved his own life. Unfortunately he was so filled with joy that he began laughing once more and as such choked on more of the afterbirth remains. The cat decided this was going to be a long night, as it was against the rules of the pussy to  let a child die if it could be prevented. So he stayed with the laughing babe, removed him from the garbage can and waited for someone to come and retrieve the child.

The most important things in life often happen while waiting for things that never will.

Chapter 2:

Oliver October liked money. He liked money like Buddhist monks secretly like Judas Priest, like Wall Street bankers take off their suits and wear pajamas when they get home from work. As in he liked money but also liked his dreads.  He had all the freedom accessories from expensive shirts emblazoned with folk heroes to incense that stuck to his fine silver spoon skin.

Like many such schmucks he led a double life. He attended yoga class, did his stretches, breathed in slowly, enjoyed each and every exhalation shortly before enjoying a refreshing smoke.  He often went to protests and enjoyed smiling at the homeless and giving them nothing when they asked for something. He purposefully kept 7 dollars in dimes, nickles and quarters in his pockets at all times, simply to see if someone would ask him for change. He always smiled kindly and refused.  Because Oliver October liked money and it went beyond the normal Western desire for purchased items.

He began as a coin collector.

At first it was the typical child-like desire for otherworldly adventure, buying worthless coins from different countries and pretending to have acquired these coins during his extensive travels.  Eventually Oliver ran out of  drawers to keep his coins in, and the local Coin Shop ran out of cheap items for him to buy for expensive prices. When he went to sell some back to acquire more deluxe items, such as coins that actually had some real value to someone other than his mediocre childhood friends, the owner of the store very wisely refused to buy back any of it.

It was at this moment that October began collecting real money, not for the obscurity of its value or for its story but because he could trade real money for things he wanted. Soon the closet was packed full of water jugs filled with pennies, nickles, dimes, quarters, loonies and twoonies.  He would often go out with these jugs and ask for money for impoverished children. He wasn’t making an adults salary so he counted himself as one such impoverished child.  During world crisises he made a mint.

So one day as he walked down Main Street, body sheathed in sweat from hot yoga, het met the happiest homeless man.  He has aged much since we last saw him coughing up afterbirth.

He appeared to be asleep but his ever present grin remained on his face. The happiest homeless man happened to be known as Harold.  Not Harry. Not that the Happy Homeless Man would raise an ire over such a small thing.

Oliver October wondered if he might be dead. He also wondered if he might be so sound asleep that he might not notice if Oliver were to purloin, borrow, thieve a few coins from his Tim Horton’s Cup.  He was really running quite low on pennies after spending almost five dollars at Karma yoga.

He tried the polite approach first.   He asked if the homeless man had the time.  Harold just grinned and turned over in his sleep.

Oliver took a breath mint from his pocket and slipped it into Harold’s drooling mouth. He had gotten the mint from someone at karma yoga but felt he should give the man a little something for his troubles.

He reached into the cup to take a few pennies for luck. Then nickles and dimes in case he needed to leave a tip. Then thought he might need to take the bus, because after all he was carrying a yoga bag aon his shoulders, so he decided to take just a few loonies and twoonies to help him on his way.  He took out another courtesy mint and slippedit into Harold’s mouth.
At least he would wake up with excellent breath.

He took the coins in hand and then something very strange happened.

“Dirty hippy, let us go. We likes you not, you lippy lout have been caught,” said a strange voice from within his clenched fist.  “In my time you’d be shot.”

He looked around, sensitive to criticism. Someone must have seen him. He lifted his trendy shades perfect for night time wear and saw no one.

“Sweat covered son of a millionaire, you are taxing our patients, as your doctor father taxes his patients of their savings and time,” once more spoke the voice from his close fist. “Luck is not blind. It has a head, for what you have done to Herald, we should burn you for a tale and leave you dead.”

He reluctantly opened his grasping fingers.

The Queen of England was glaring at him. “You blaggard. How can you rob Harold? Do you have any idea who you are robbing?”

A beaver slapped its harsh metal tall indignantly. “You will be damned for robbing the Happiest Homeless Man!”

A silver queen echoed the copper queens original distaste but added a little twist of her own. “You must be mad if you hear coins talking. Run for the hills hippy and leave the change behind you..”

Oliver October was struck speechless.

“The Happy Homeless Man?”

“The Happiest Homeless Man,” repeated the coins held in his shaking fists before beginning a rousing song.

“He is the happiest homeless man and much to your chagrin, he was born in a garbge bin, with a heart so sweet that in Oz it would be desired by the man of tin, he is so sweet and guiltless, he could never commit i a sin, so kind that everyone in the world should be in love with him, and know that against him, you’ll never win,” sang the change.

“Why?” asks Oliver.

“Because he has a tiger guarding him!”

It was at this point that a rather large tiger jumped from an alley and clobbered Oliver in the face with a rather large paw. See Monkey had never actually been a cat and his family had been a zoo and he was totally and completely a tiger.  After a rather brutal beating, Oliver convinced his parents to cease donating their monthly stipend to the World Wildlife Federation.

The Happiest Homeless Man woke from his sweet sleep, saw Monkey and happily sighed his way into the day.

“What adventchy shall we have today, sir Monkey?” asks Harold.

The tiger growled.

“Shall we talks to the nice people, collect a tintsy bit of change and get us some grub?” he asks.

In the distance Oliver was doing quite a little bit of screaming in his tattered brand name clothes. As a result a crowd was gathering around him. They didn’t like his explanation of how his clothes had been torn and why certain parts of his body were more exposed than would be considered polite in societies where politeness was much of  a concern.

See Harold, the Happiest Of Homeless Man happened to beg in front of a little coffee shop deep in the territory of the notorious gang known as the Jackets.

They were known as the Jackets for their propensity to wear jackets even during the hottest days of summer.  For the Jackets it was a matter of the utmost importance to be properly dressed. The type of jacket did not particularly matter to these ruffians. It could be a blazer, a sports coat, even a rain slicker. As long as it covered your arms, shoulders and may or may not have come equipped with a hood to deal with inclement weather. They were very concerned with decorum. As such Oliver and his torn yoga pants disgusted them.

Years before they were called the Gentleman for their famous dislike of all things impolite and uncivil. They were known for swarming men who were rude to ladies, who improperly recycled and lately had taken a keen dislike to persons who forgot to properly dispose of their cigarettes. They ruled these streets and would not take any insult to their domain. Their tribal yells included such every day phrases as “Thank You” and “Your Welcome.”  Thankfully there were few restaurants in the area because if there were customers who neglected to tip might have gotten their skulls cracked.

As a result Oliver October was in for a bit of a scare.  The leader of this tribal game of polite thugs, Jamie Jasperson, wore a fedora, tuxedo and liked to use his cigarette holder to wrap knuckles and slap wrists.  His secondary weapon, which he happened to be prefer, was a metal ruler of approximately 30 cms centimeters in length. As a child he had been taught lessons by his fifth grade teacher at the end of a ruler. As a result Jamie Jasperson had a horror of mathematics and considered geometry to be an abomination. However, first and foremost he respected discipline and, like all men of manners and faith, would die to defend the truths he learned in grade five.

Since Oliver October had breached decorum by his torn clothes, and filthy mouth(he was swearing quite a bit due to his injuries at the hands(paws) of Monkey) Jamie Jasperson, or JJ the Great as he will be referred to henceforth, decided it was time for a good old fashion swarming.

So the gang swarmed.

Off to the side, singing a happy tune was Harold and Monkey.

“This is my begging song, don’t get me wrong, I love the street, it’s where I was born and where I belong. Methinks I could dance a jig for a couple of drinks, of that old fashioned delicious thing brewed in sinks, I’ll always be fine, whether I am drinking a little bit of wine, every day on the street is fine, I’ll never fail, life is better where I spend my time,” sang Harold.

For a second the gang turned to  him and paused in their act of discipline.  Oliver October moaned slightly, wondering if it had been stupid to try to steal this singing crazy person’s spare change.  Harold raised two fingers and smile, showing his brown blackened teeth.

“He has a peace sign,” says Jamie Jasperson.

“That was my line,” says Harold.

Monkey growls and paces into the street. The Jackets are quite surprised to see a Tiger in their midst. Jamie Jasperson decides to take charge of the situation.

“This beating shall henceforth be labeled finished.  After all it is now tea time,” proclaimed Jamie Jasperson.

The Jackets take their leave, enter the local Tim Hortons and order themselves various coffees, teas and biscuits to celebrate their noble behavior.

Oliver October promptly passes out.  Monkey takes his torn clothes in his mouth and begins to drag him to a homeless shelter.

“I’ll walk with my feets, soon the nice people will give us all something good to eat,” sang Harold.

This would be the first day of the rest of Oliver October’s life.



One Response to “The Heroism of the Happiest Homeless Man Part#1”

  1. Troy
    July 28th, 2010 @ 1:12 pm

    Great story … You had me pulled in.

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    Michael Kimber is a 26-year-old journalist who suffered a nervous breakdown on November 3rd, 2009. On March 28th, 2010 when he recovered from mental illness, he began writing a blog called Colony-of-losers. About falling on your face to figure out who you are and the hilarious antics of a blond jew. What began with a few friends and his mother reading has become a cult phenomenon, averaging 10,000 views a week, receiving praise from Commonwealth Award Winner Shandi Mitchell and many others. On, November 3rd, 2010, the one year anniversary of his mental breakdown he signed with Anne McDermid and Associates, the largest literary agency in Canada. In a year he went from wearing pajamas, making his couch depression HQ to leaving his hometown for the Toronto, where he exclusively wears business suits and the armor of ancient Greeks. Don't worry, he's still choking on the feet he contently sticks in his mouth and making moments awkward just by being part of them. During these struggles he met other talented bastards and drew them into his circle. Peter Diamond became his illustrator. Patrick Campbell his video editor and part time photographer. He recently added the incredibly talented John Packman as Colony of Losers Toronto photographer. Without the support of the Colony of Losers, Michael Kimber would be nothing. Welcome to the losers and the success that comes from utter and complete failure. You aren’t alone. Follow him on If you’d like to hire him for a public speaking engagement for mental health events in Toronto, like to arrange an interview, offer millions to publish his book or for another reason contact Michael please email him. And join his facebook Colony of Losers.

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