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This week's edition of New York magazine's Look Book presents a problem: Sam Masters, at right, is but a wee lad, a high school junior at Browning. And yet? He deserves a firm smack for being a total Stroke-in-the-making. Masters is a David Bowie fan with a band called the Deadly Monks, he acts through the New York Film Academy and is drawn to Jude Law's role in Closer, his clothes are "funked" and tight, and his girlfriend Destine is everything he's ever wanted (because she, too, is a big Bowie fan). And even though he doesn't say so, you KNOW he spends his weekends skanking around Tompkins Square like he's the next LES Jewels. After the jump, Intern Alexis solicits insight from the Imaginary Socialite, Fiorella Valdesolo, and Alan Wilkis on where young Sam is headed in life.

The Imaginary Socialite, internet personality

Where do you see Sam Masters in five years?

Sam Masters will be "funking it up" in a Harvard Law interview, explaining why David Bowie lyrics are, in fact, central to our country's judicial principles.

Ten years?

Sam Masters will be my Second Husband.

In last weekend's "Education Life" section of the Times, there was a feature on what kids wore to their SATs. What would our boy Sam wear to his?

Sam disguises himself as Samantha and wears a Juicy Couture velour sweatsuit; if his board scores come back badly, he can claim he never took them, and if they turn out well, he can title his Yale Early Action essay, "Do You Know What It Feels Like For a Girl... In This World?"

What do you think the lower half of his body looks like?

See above: I'll have that answer for you in ten years.


Fiorella Valdesolo, magazine editor

Where do you see Sam Masters in five years?

In five years time, our boy Sam will be starting his final year at Brown University... he would have preferred to enroll at Oberlin, but generations of Masters have attended Brown and though his parents are "hippies" they didn't relish the idea of Sam barefoot rolling granola in Ohio. They did agree to let young Sam spend his junior year in Prague which was a life changing experience for him. Because really Prague is just the poor man's Paris and everything there is so mysterious. And it was all so very inspiring for his music... though, fans will be remiss to discover, he's no longer a part of the Deadly Monks. They broke up after their senior year at Browning when both the drummer and guitarist decided to go to Princeton, making their bi-weekly bong hit jam sessions virtually impossible to pull together. Masters recruited two foreign exchange students freshman year at Brown to form the Priest Stranglers, and though they dominated the Battle of the Bands that year, pocketing gift certificates to The Cheesecake Factory and matching Che Guevara t-shirts (come on, it's Brown people), by the end of sophomore summer they were relegated to playing accompaniment for the girls at The Foxy Lady for Sunday's boobilicious Legs 'n Eggs brunch. But it was no loss for Masters who prefers the challenge of performing solo anyway. Nowadays when not working on a hip hop adaptation of Waiting for Godot, Sam has been combining the depth and complexity of his stage presence with his musical stylings into a kind of spoken word poetry... not the ghetto kind though. Exhale.

In ten years?

This may come as a huge surprise, but Sam is still trying to find himself. He spent some time in an upscale ashram near Canada before being kicked out for an inappropriate relationship with the vegan chef's teenage daughter. He pretended to be homeless for a month camping out down on the Bowery to get inspiration for his lyrics, but a beard has never really suited him so he's now living in the basement rental of his parent's Park Avenue townhouse (wait, not all hippies live like this, what?). Sam recently ran into Charles (the drummmer from the Deadly Monks) at a New Yorkers for Children benefit his parents dragged him to, and after failing to convince him to reunite, he drunkenly agreed to give the financial world a go and accepted an, ahem, paid internship with him at Skadden and Arps. He's been there a few weeks now, and though he's discovered that eyeliner in the workplace is frowned upon and that wearing a tie has lost its sense of irony, he really doesn't mind the environment that much. Besides Charles scored him his very own Skadden gym bag, which when worn on the subway is a real babe magnet. But don't think for a second that Sam has gone all corporate... he's still an artist man. You can catch him at The Continental every other Tuesday with his David Bowie cover band, and if he can finally land an audition for Law and Order, you may soon be seeing him as a victim on NBC. Oh, and he's stalking Destine.

In last weekend's "Education Life" section of the Times, there was a feature on what kids wore to their SATs. What would our boy Sam wear to his?

The SATs are the SATs. But naturally Sam would need to funk it up a little bit. If not just for his own peace of mind, but to inspire his classmates to not be afraid to express themselves. I'm thinking he would go for the smart, dandy look - cords, but the tight ones, so he doesn't come off too preppy, a vintage tie (duh), plus the requisite Latin teacher button down knit cardigan with the suede elbow patches. Oh and just so he doesn't completely lose his edge, Sam would draw on the Ziggy Stardust third eye, because Bowie rules and, you know, for wisdom and shit.

What do you think the lower half of his body looks like?

The kid's got some wicked cankles man! I mean geez, those crazy ass Bowie platform shoes would make anyone's ankles swell.


Alan Wilkis, musician and film/TV music type

Where do you see Sam Masters in five years?

In five years, Sam's band the Deadly Monks will be immensely popular. Sam will be heralded for his bass-playing/singing a la Geddy Lee, and his hair will look really great, but die-hard hipster fans will be talking about the early years (the "Browning" years) before Sam sold out.

Ten years?

The Deadly Monks will have disbanded after Sam's soul-searching visit to the Himalayas, upon which he will decide to become a REAL deadly monk... like with numchuks and swords and cool religious powers! And he'll have these sweet poison-tipped arrows that he saves for the heathens/non-believers.

In last weekend's "Education Life" section of the Times, there was a feature on what kids wore to their SATs. What would our boy Sam wear to his?

Sam chose not to take the SATs in order to get a nice head start on his career in acting and music. Who needs college, anyways? Had he gone, however, he would have worn an argyle unitard and some eye shadow... And maybe a codpiece if it was cold out.

What do you think the lower half of his body looks like?

My best guess? Tentacles. A whole bunch of tentacles. And slime. But the slime smells really good like Orlando-Bloom-good. That's how he scores all the chicks. And perhaps an ironic pair of Doc Martens on two of the tentacles.