Character sketches of the people I always imagined would form my entourage.

The Whipping Boy (a.k.a The Donald)

Spends the majority of his time making sure other people have everything they need. This is due to him being the youngest of 11 children and his father being a butler. As a result of this upbringing, he is unable to walk past an unmade bed without making it and cannot stand the sight of unfolded clothes. He also has a passion for placing and picking up take-out orders. And posses an uncanny ability to recite the exact location of every convenience store and strip joint in a 50km radius of his precise location–along with providing the approximate duration (give or take 1 minute 46 seconds) of a round trip.

The guy who knows the guy who can get you anything you want (a.k.a Snatch)

All it takes is one phone call.

The rest is pretty much self-explanatory.

The Gambler (a.k.a Robert Poulet)

Will literally bet on anything. How long you’ll be in the can. How many times you wipe. The over/under on how many seconds you spend washing your hands. It’s a little known fact that his “father” won him in a game of Chinese checker from a band of gypsies on the same night he came up with the phrase “winner, winner chicken dinner”. Every time he goes to Vegas, he does a bang on Rain Man impression that gets him high roller treatment and constant attention from a bevy of showgirls.

The Know-it-all (a.k.a 202)

The real life Doogie Howser–only not a doctor. He has an IQ of 202 (hence the nickname) and lives to hear people say, “I bet you didn’t know.” After he proves he did in fact know, he goes on to inform them he graduated from Yale Summa Cum Laude at the age of 13. Attended Oxford on a Rhodes scholarship and graduated with honours at 16. By 19, he had been to space, twice, and was asked to leave Jeopardy after he answered every single question over the course of 27 straight shows. He loves game night, hates small talk and is currently working on his own encyclopedia.

The ridiculously rich yet rebellious heir (a.k.a Geeves)

Was toilet trained on a 24K gold toilet and, once he learned about this, grew to resent his parents for putting him through what he believes is a trite cliché. Though he enjoys the perks of being fabulously wealthy, he hates the fact he’s from old money, which makes him further resent his parents. This resentment was briefly quelled when they hired a gorgeous Peruvian housekeeper whom he eventually lost his virginity to. It quickly returned when his father was named the second richest man in the world, which, coincidentally, was announced on his 19th birthday, the very same day he was given his own private jet and control of his massive trust fund. He has since emancipated himself from his parents and has pledged to use his trust fund to bring his favourite movie, Brewster’s Millions, to life.

The Celebrity Sibling (a.k.a Broseph)

Spent his life in the shadow of his world-famous, multi award winning, box office king little brother. Though it’s common knowledge that the relationship garnered him a number of supporting roles in movies he wasn’t talented enough to get on his own merits, in his mind, he’s an A- not D-list celebrity. Somehow, he’s able to flaunt this “celebrity” status to bypass lines at nightclubs, get into 5-star restaurants and pick up women. (9 times out 10 the latter doesn’t work unless he promises to give them his brother’s number afterwards.) When people see him in the streets, ignore his career, and instead ask what his brother’s doing next, he has to fight the urge to kick them in their neither regions by immediately doing a series of sun salutations.

The Sartorialist (a.k.a Fancy Pants)

Believes that wearing floods is a fashion statement, not a faux pas–but only if you compliment them with suede loafers sans socks. Was the driving force behind the recent trend that saw people pair strips with plaid. Is also trying to remove the stigma from sporting a moose knuckle. When he’s not drawing attention to his daring fashion statements, he’s busy petitioning governments around the world to ban the sale of novelty t-shirts and make it a felony to be caught wearing one. The only drawback to his impeccable style is that, when not throwing themselves at him, women think he’s gayer than Clay Aiken.

The Bodyguard (a.k.a Beans)

A mixed martial arts fanatic who knows absolutely everything there is to know about the sport. Whenever anything MMA related is on TV, he’s an immovable object, and will not acknowledge anyone around him unless it pertains to the fight. If he ever wanted to, he could be a force within the sport. Unfortunately, he’s a Pacifist, and, he suffers from a crippling fear of making eye contact. To combat this fear he wears sunglasses at all times. Luckily, at 6’8’’ 315 lbs., his mere presence is what people refer to as “shit your pants intimidating.”

Tags: Doogie Howser, Entourage, Jeopardy, mixed martial arts, moose knuckle, Oxford, Rain Man, shit your pants, showgirls, Snatch, strip joint, Vegas, virginity, Yale