Lee Mason (not his real name) has yet to return a single one of my phone calls. Sometimes his cell phone just keeps ringing. Other times, a mysterious click is followed by a long, deadening buzz. If I’m lucky, the voice mail picks up. “I’m out walking the Spider Web,” says his deliberately coy message, a nod to last summer’s blockbuster Batman Begins and Bruce Wayne’s tendency to vanish quickly. When I finally catch the sly 16-year-old, he clicks over to call waiting at least five or six times, but won’t tell me who’s on the other line. I’m quickly realizing that the only earthly creature cooler and more elusive than a hot, young Hollywood celebrity is a hot, young teenage boy in the throes of adolescence.

Finally, Mason’s mother, a semi-famous character actress, secures me a date with her son. I prune to appear modishly disheveled, opting for tangled, unwashed hair, Converse high-tops from 11th grade and a Cure concert T-shirt that I picked up at Wasteland. I drag along Paul, my geeky-chic husband, who, God help him, tucks his oxford shirt into his chinos, and together we’re standing outside of Hollywood’s McCadden Place Theater waiting for our teen dream to show. Shaye pulls up in her scrubbed-up Saab and Mason tumbles out, all oversize sweat shirt and jeans shredded within an inch of their existence. His soft brown hair falls in diagonal wisps across his forehead and his favorite sneakers are one wear away from splitting apart at the soles. “Hey,” Mason says to my husband. “Cool shirt.”

We’re seeing Coke-Free J.A.P., something I have a hunch Mason will take to. Sure enough, the one-woman show about a neurotic, Jewish Manhattanite 92 days sober reminds the self-reflective teen of his struggles as a recovering crystal methamphetamine addict. He laughs at the protagonist’s casual references to cocaine, her hysterical sociocultural rants on everything from sex to her psychiatrist, and the ongoing frustration she has over her strained relationship with her emotionally detached father. It’s unnerving how closely Mason relates to the play’s sophisticated subject matter; you’d sleep better if he were just a tad more naive. But as anyone who’s spent time with teenagers knows, adolescent naiveté has sadly gone the way of the dinosaur.

I first met Mason three years ago when he slogged through the door of the fourth-grade Hebrew class that I taught at Temple of Hollywood. At first catch of his cherubic features — bright, clear skin, plump mouth, a smudge of pale cherry-pink on each cheek — it was inconceivable that he spent much of his early teens scoring speed in cramped alleyways off Melrose. But as playwright Arthur Miller wrote: “Where choice begins, Paradise ends, innocence ends.”

Mason was 14 years old when he spent 94 days in a tony youth rehab center in Los Angeles that he dutifully refuses to name. He made friends there, he explains — heroin junkies, pill poppers, pot fiends — whose privacy he needs to respect. As part of his rehabilitation effort, Mason got a part-time job as my teaching assistant. Granted, he never really assisted, because he was too ironed-out from all the antidepressants and antipsychotics he was prescribed. (Life sans speed moves pretty damn slow to a kid who was once hooked.) During my class, he spent every week for two solid hours at the back of the room reading Chuck Palahniuk novels and logging on to his Myspace.com account. Sometimes he’d steal out early or skip class altogether in order to make his daily Narcotics Anonymous meeting out in Pasadena. A pill popper during graduate school who survived a few touchy-feely group therapy sessions of my own in rehab, I fast became Mason’s de facto mentor. He’d bend my ear about colleges, benzodiazepines and Clearasil. Mason’s observations on the state of elementary-school education were precociously blunt.

“The only thing that I’ve learned by hanging out in class,” he announced one day over doughnuts and milk during recess, “is that even at the age of 9 you can completely tell what kind of adult a kid is going to be.”

According to Mason, there are two kinds of teenagers: Old Spirits and everyone else. Within these two main groups are a plethora of subcategories into which teenagers of every type get sorted. The Old Spirits, the category into which Mason falls, wear black and are messy, inscrutable creatures, with troubles that rival those of any seasoned, hard-living adult. Kurt Cobain is a hero.

The Old Spirits, says Mason — and there are a lot of them — can’t relate to their airbrushed portrayals on film and TV (The O.C., with its soap operatic subplots and cast that looks like it stepped out of a toothpaste commercial, doesn’t count — neither does MTV’s vapid reality counterpart, Laguna Beach). For all the chick-lit manifestos on the shelves about everything from anorexia to rape to alcoholism to promiscuity, there’s not a lot of dick lit to match it. And despite a recent flurry of nonfiction books on adolescence over the last few years, girls get most of the press. With the exception of the commendable Adolescent Boys: Exploring Diverse Cultures of Boyhood, co-authored by associate professor Niobe Way of New York University and Stanford lecturer Judy Y. Chu, most of the material on teenage males focuses on the upper-middle-class, white demographic, while the few tomes on minority male teens tend to reduce them to thuglike stereotypes.

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For Mason, the PG-13 interpretation of the post–junior high crowd as depicted in such movies as Mean Girls and Clueless, with their plots revolving around a lot of pastel miniskirts and designer skateboards, is kid stuff compared with how real-life teen cliques, especially the male-dominated ones, play and act, many of which project, collectively, a striking cynicism shades darker than a Dostoyevsky novel. “You could say the Old Spirits stick together,” says Mason with a long, tired sigh. “We’ve experienced way more than we should have.”

Lee Mason is an Indie Fuck, one of the Old Spirit subcategories. The membership rules are as follows: Have hair in front of your eyes, own at least two shirts promoting bands too obscure for anyone but another Indie Fuck to know, have a Livejournal.com or Myspace.com account, drink way too much, own The Royal Tenenbaums DVD, be so not-sure-you’re-gay it’s sad, and listen to music by the likes of Modest Mouse, The Shins and Elliott Smith, preferably the posthumous stuff. Most Indie Fucks are advanced Emos, cohorts of the teen clique prone to black clothes, crying a lot, self-mutilation and listening to bands like Dashboard Confessional and Death Cab for Cutie. Failing geometry is always a plus, as the junior did last semester at Alexander Hamilton High School, with lectures on isosceles triangles falling mute on ears iPod-ed out on way too much Bright Eyes and Neutral Milk Hotel music. In general, Indie Fucks like organized education as much as Howard Stern likes the FCC.

For two exuberant months during his sophomore year, Mason ditched every single period except geometry and French, ducking out after homeroom attendance and returning in time for sign-out. He’d hunker down to smoke butts and read David Foster Wallace novels under the overpass of the 10 freeway. He got really into Infinite Jest. “It’s cool how the main hero loves that nobody knows he’s stoned, better than he loves actually being stoned,” exclaims Mason. “I loved being fucked up when people just thought that I had a really big appetite.”

Sometimes he’d scratch out notes for “The Cons of Patricide,” a novella that ?he’s writing about a kid who kills his parents and then winds up getting lost in ?the desert.

Then one day he got caught skipping. And got into a whole lot of trouble. His mom yanked him out of Hamilton by the hood of his slashed-up sweat shirt and enrolled him in Concord, a school whose educational philosophy encourages “challenging academics” within a supportive social ambiance. (“Yeah, rich kids and drugs,” jibes Mason.) Valentine’s Day rolled around so he broke up with his girlfriend and decided to become bisexual. “I know,” he says, acknowledging the cliché.

Lately, Mason “hooks up” with random girls at parties. “I’ve only fucked, like, five girls total,” he casually tallies. “Unless you count getting head and stuff. Because when I say ‘hooking up,’ I mean below the waist. So, in that case, I’ve been with thirty-five.”

A few months back, Mason’s mother caught him screwing some girl in her tidy house up on Mulholland. She definitely got dramatic over it, implementing a decidedly Clinton-esque don’t-ask-don’t-tell policy. “I can do it in the house but she can’t know about it,” says Mason, whose parents got divorced when he was 13. He didn’t talk to his realtor dad for a year (an Indie Fuck rite of passage).

“I haven’t fucked in my dad’s house yet,” Mason reveals, drawing languidly on his cigarette like a character in a Luis Buñuel film. “So I don’t know what he thinks.”

It’s no Pentagon secret that teenage boys are horny, but that doesn’t mean they’re all reckless.

“Most of the boys I’ve worked with talk about sex way more than actually have it,” assures Dr. Robert Butterworth, a prominent Los Angeles–based trauma psychologist and media commentator who works closely with teenage boys. For the first time since the 1970s, teen sex is down. More and more, boys are the ones postponing first-time sex. In fact, a 2002 survey by the National Center for Health Statistics reported that out of 3,000 teenagers polled, 46 percent of adolescent males were sexually active (compared to 47 percent of adolescent females), a significant drop from 55 percent in 1995. Not that teenage boys are retiring their Trojans just yet (roughly three-quarters of sexually active young males claimed to be using contraceptives). Many cite sexual exploration as the sole driving force behind the race to become Mr. Popular. “We see it in the animal kingdom,” says Butterworth. “Cavemen hunted in groups, and all throughout the ages there have been competitions in terms of strength to see which male could be the one who breeds.”

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Vincent Estrada has to wait until Tuesday to find out if he’s the one who gave an ex-boyfriend chlamydia. It’s Thursday, and the 17-year-old can barely contain his trampled nerves. When the Hollywood High senior and I first met, it had been only two months since he came out of the closet, two and a half since he and the boyfriend called it quits.

“I know that it’s going to work out,” the Filipino-American tells me in a soft voice still full of hope. We’re sitting opposite one another in matching right-handed desks in the hallway outside Estrada’s English club. His large brown eyes skittishly dart back and forth. “I’m going to either move there or get a job or he’s going to move here.” But this is before the ex-boyfriend called up to accuse Estrada of giving him a venereal disease.

Estrada realized that he was gay when he was in ninth grade but didn’t tell anybody until the 11th, and even then only a few close friends. He shaved his head at the end of 10th grade to mark his coming out, and now the closely cropped coif represents more than a mere aesthetic choice — it’s a talisman. He repeatedly rubs his hand over the spiky ends as if to remind himself of his newfound freedom.

“I was popular before all this,” says the virtuoso drum major — he’s been active in music since the third grade — who kept his sexual orientation under wraps by only dating guys from other schools. “But once I told a few people I got even more respect. Now, it’s like, ‘You gay?’, and I’m like, ‘Yeah, you like me or something?’ Everybody loves me. I’m popular because I am gay.”

Everyone does like Estrada, especially the girls. A bouncy gaggle of sophomore Lolitas with long, smooth hair and snug-fitting cardigans glides past him in the halls, hollering his name and begging for afterschool hang time with their fab G.B.F. (Gay Best Friend). “Girls can talk to a gay guy about anything,” boasts Estrada, who floats easily from clique to clique.

Respectable boyfriends are far harder to come by. Estrada once courted a straight male ballet dancer, but to no romantic avail. It crushed him. Since then, the boy with the signature ethereal smile has favored swarthy, smooth-talking Latinos into hip-hop and late-night clubbing who wear sprayed-on leather pants and douse themselves in department store cologne. “I’m in the gay scene,” says Estrada, who slides into any over-21 club he wants and never gets carded. “Everybody knows who I am. The little, gay Asian boy with a drop of Spanish blood.”

But not everyone knows that Estrada is gay, namely his Filipino-born parents — his father is a mail carrier, his mother sells mannequin dolls — whom Estrada dubs “old school” and “so strict about everything.” And they certainly don’t know that their youngest son (Estrada has an older brother) recently toddled into a Hollywood-area free health clinic to get a blood test for chlamydia. “They won’t read this article,” he tells me. “But even if they do, they have to accept me, whether it’s now or in ten years.”

Tuesday arrives and Estrada does not have chlamydia. I remind him that this could only mean one thing, and Estrada’s voice goes hollow. “I can’t deal with hurting someone,” he says shakily. “So it’s better that I’ve found out he cheated on me.”

In a Studio City Starbucks on a balmy day last spring, Adam Teitelbaum tousles his head of thick, wavy hair, his facial expression bearing an uncanny resemblance to the wide-eyed guy on the movie billboard for The 40-Year-Old Virgin. The blemish-proof, salon-groomed teenager draws a sip from his decaf soy latte and adjusts the collar on his Izod Lacoste polo shirt — up is in again. “I really like collared shirts,” gushes the self-professed Prep. “I really like looking neat.” I recommend Whit Stillman’s indie ode to preppiedom, Metropolitan, a suggestion totally lost on the suburban, generation-centric 17-year-old. “Whit who?” he asks.

Teitelbaum is pretty much your average white, upper-middle-class nice Jewish boy: He’s on the honors track at New Community Jewish High School in West Hills (a private school with a junior class of 43), is the executive vice president of United Synagogue Youth Far West region’s local chapter, and he’s had a steady girlfriend for the past 10 months. “I’m not even thinking about marriage!” he exclaims when asked about the possibility, like I must be totally off my meds for inquiring about it. If this is a teen in the murky swirl of mad first love, he certainly doesn’t show it. Teitelbaum is poised, in a decidedly John Kerry-esque way, like neither he — nor his hair — has ever once given over to a parking-lot fistfight over some saucy lass in biology class.

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“There’s a pretty intense level of sexuality at my school,” brags Teitelbaum a smidge too enthusiastically. “Only a few of my friends are going all the way, but we pretty much do everything else.” Hot and heavy rep aside, there’s not a lot of social pressure to have sex at New Jew. “I don’t think it’s because it’s a Jewish school,” he swears. “It’s just such an intimate atmosphere, so people accept you for who you are. It’s not like you can’t be here if you don’t have sex ten times a week.”

The 11th-grader’s gal pal — he remains mum on her specifics — came around without any hot pursuit from Teitelbaum. He’s always had lots of friends who are girls (“I’m really in touch with my feminine side”) yet openly admits, “No offense, but girls are bitches.” Why, he wants to know, can guys kick the shit out of each other on the basketball court but as soon as the whistle blows they’re all best friends again, and with girls everything goes so much deeper? “Up until last October, I didn’t even want a girlfriend,” he declares. He’s still not completely comfortable with the idea. “But then one day I was like, okay, I’ll try it out. I mean, what the heck.”

His relationship with his girlfriend revolves around a lot of PG-rated activities: “Dates are, like, whatever — a movie, a bowl of soup at Jerry’s Deli, easy things that don’t require a lot of cash.” His parents — Mom is a nurse at Thousand Oaks Hospital, Dad is a talent manager — give him $45 a month in allowance, but he tirelessly campaigns for more. He also works the odd job for extra dough — this past summer he was a counselor at Camp Ramah in Ojai. For 50 bucks and a refrigerator full of soft drinks, he’ll baby-sit. Sometimes he helps out his friend who owns a DJ company. “He does all the music stuff,” says Teitelbaum, finger-combing his hair. “I sit and look pretty.”

Teitelbaum tried Agoura High School during freshman year but found the academics and pressure to be good at sports too competitive. “Public education wasn’t right for me,” he says. Now, the boy with the perfect curls has secured a plum spot in the inner sanctum of New Jew cool. He’s a year-round athlete who plays water polo, soccer, lacrosse and does track. He was student body president and at interview time was running for class president.

“I’m popular,” he says matter-of-factly, like there’s nothing he could do to help it. “It’s my personality and the fact that I’m incredibly good-looking,” he says, only half joking. But, in a class of 43 students, ?is there anybody who’s not popular? Teitelbaum balks, then quietly admits, “I’ve never seen anybody eating alone.”

Everyone I talked to thought of himself as “popular.” Skewed self-reflection? Could be. Or maybe “popular” has become popular thanks to there being so many social groups to which a male teen can adhere. Whether you’re a sagging Old Spirit or someone of less sexual and social experience, there are enough cliques out there to afford all but the most socially inept a sense of fraternity.

“I hear you need a colored kid,” Cameron Brooks cracks over the phone. “Or should I say African-American? Or just black — which sounds better? Can I say black? Yeah, that’s cool. Black. I’m the black kid.”

I catch 17-year-old Brooks (a.k.a. “XkillACamX” — like many of his peers, Brooks uses an unpronounceable nickname to stay under the radar of authority figures) with his mom en route to soccer practice. He also surfs and likes to skateboard. He doesn’t drink or do drugs. His dad is a surgeon but his parents are divorced, so money can be tight, which is why he’s one of the Funded Kids at Encino’s Westmark High School, a school touted for its tiny class sizes (13 students on average) and provisions for students with special needs.

Brooks has attention deficit disorder.

“My ADD has never affected my popularity at school,” says Brooks of the learning disability that the American Psychiatric Association estimates afflicts between 3 to 7 percent of schoolchildren in the United States. “But it did affect me within classes because I wanted to do everything on my own and I couldn’t. I thought that I was dumb. When I first found out that I had ADD, it wasn’t a relief because I was confused. Did I have a problem? I didn’t know exactly what was going on.”

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Now, Brooks has come to embrace his ADD. He takes Strattera, a new non-stimulant alternative to Ritalin — “It definitely works,” he says — and recently took part in an educational film on learning disabilities produced by Channel One Productions. He gets A’s and B’s in school and hopes to attend either UC Santa Barbara or UC San Diego. He’s had a steady girlfriend for the past year and a half. Her name is Mackenzie Brown. She’s white.

“I have nothing against dating black girls,” swears Brooks. “I’m just so . . . over all the racial stuff.”

There are plenty of places where Brooks and Brown might catch some stares, but here in Los Angeles the unheralded Westmark wrestling team warrants more attention than their interracial relationship. “As of right now I think all the racial-type differences have been resolved,” affirms Brooks, who’s dated a number of girls of a number of races. He says he never went in search of a white girl, but . . . “I know I’m only 17, so I haven’t been with so many girls, but the ones I have dated . . . I am attracted to white girls mostly. It’s just the way it is. I don’t see myself on the beach with some sort of ghetto girl. It’s not my style.”

Oleg Pantelyuck, a friendly Skater Kid with ice-blue eyes, butter-yellow hair and dashed hopes of remaining a brooding loner, had no idea what a clique was when he emigrated with his father from Ukraine five years ago. He hangs with an eclectic crew of professional skateboarders, dropouts (13 percent of teenage boys will eventually drop out of school, compared with 10 percent of girls) and junkies, but drifts around, citing photography as his greatest passion. He’s been living apart from his mother for the past two and a half years (for financial reasons, she’s still back in Ukraine), and while weed was rampant growing up in Ukraine, Pantelyuck says he has never once gotten stoned or tried hard drugs. After moving here, he had one girlfriend who was Emo, but when she began to cut herself, a decidedly emo thing to do, he distanced himself from the crowd.

“Cliques are weird,” says Pantelyuck, kneading his garnet ring–stacked knuckles back and forth. “Back in Kiev it was just all about soccer. Then again, there wasn’t much else to do back in Kiev.”

While group identification isn’t uniquely American, what seems to be the difference between teenage cliques in the U.S. and abroad is the variety of choices available here. Adolescent males in richly diverse places like Los Angeles have a cornucopia of types they can choose to identify with. Though branding is still an integral part of kid culture and self-segregation is an inarguably innate facet of human nature, teenage boys today are not stuffed in little boxes based primarily or even subordinately on race or color or creed. They can be rich and not be a Snob. They can be Latino and not run with the Cholos. They can be black and not be considered Ghetto.

Freddy Vasquez is an Outlaw. A Rebel. A Tagger. The 19-year-old has spray-painted, scrawled and marked the word Tikal across more schools, parks and cars than the Hollywood High senior (he flunked a year and had to repeat it) cares to remember. It was his crew name, he tells me, but he still doesn’t know what it means. The crew was called Mobing (sic) Over Hollywood (MOB for short), and he’s not sure what that means, either. “It’s a criminal group,” is about all the recovering vandal can explain. “Not quite a gang yet — the precursor to a gang. We would, like, battle against other people.” He flourishes a balled-up fist for emphasis. “It’s like, show me what you want, man.”

Vasquez is sitting on a stoop at Hollywood High, tugging distractedly on a boxy, blood-red Chicago Bulls jersey. The first time Vasquez got caught tagging a building, the cops let him off with a warning. They dropped the El Salvador–born teen back at his house and gave him a good shoving off. The second time, he was booked. He landed a court date and got sentenced to community service — cleaning up the streets. “It’s no big deal,” argues Vasquez. “Almost everyone is a Tagger — the Pretty Boys, the Skater Kids, the Hip-Hop Kids.”

Still, it’s hard to picture, say, Teitelbaum taking a felt-tip pen to Crossroads, or Brooks brandishing a paintbrush across the Brentwood School, but Vasquez insists. “Everybody,” he says.

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Vasquez blames his involvement in MOB on his growing up poor — Mom is a Beverly Hills nanny, Dad remodels buildings. “There was nothing more to do than kick it,” he says. “So I started hanging out with some people, you know, got drunk at their houses, smoked a lot of pot. The next thing, it’s like I’m trying to get into this crew so we could kill everybody. Not kill like dead, but kill, like, write on top of everybody.”

Tagging made Vasquez feel important. Pledging membership to a core group of individuals, forget its illegal mission, provided Vasquez with a fundamental sense of esprit de corps. In a way, he was no different from a pencil-necked Geek who joins up with the geometry club.

But moving away from the family group can be a treacherous journey. Vasquez began to lose himself in MOB. In the end, the rules of MOB proved more rigid than any previously set forth by adult authority figures, and Vasquez buckled under the pressure to remain loyal to its cause. He doesn’t tag much anymore. He wants to go to college and not meet the dead-end fate of some of his former tagger friends (one was deported; another did a year in county jail).

“I’m trying to cut down,” says Vasquez, gnawing on his fingers like a chain smoker tapering off a two-pack-a-day habit. “But it’s hard. I have so many haters because I look better than them, dress better than them and because I was in a crew they didn’t like.”

Vasquez claims he threw down four times with one particular bully. After one fight, he says, the bully showed up at school with his mom in tow and a bloodied towel stuck to his face, demanding that Vasquez pay the medical expenses. “I was like, no fucking way. He was the one who came up to me first. I don’t back down from anything. Nobody disrespects me.”

These days, Vasquez doesn’t have much time to fight. He’s big into fashion (Air Jordans and oversize sports-team jerseys), reggaeton, and Virginia, his girlfriend of two years who’s a Nerd, has a 4.2 GPA and has never smoked marijuana. “I think she might be one of the great ones,” beams Vasquez, who works the eight-hour graveyard shift at Wendy’s, seven days a week. He gets off at three in the morning, heads to school at seven, then after school spends a couple of hours with Virginia before scooting back to work. Sleep happens. Occasionally.

“When you’re poor,” yawns Vasquez, ?“you gotta work twice as hard as someone who’s not.”

Vasquez says he doesn’t have time to worry about whether or not he’s popular. “Cliques are dictated by wealth,” he declares. “The dudes in our school with money don’t do anything but play sports after school. They don’t get into gangs because there’s no reason. They already got somethin’ going on. Cliques are for rich kids.”

I begin to wonder what might become of these teenage boys. I worry about them. What happens to the Indie Fuck and the Prep and the Outlaw? Where will they all end up when high school ends, their cliques dissolve and their old labels go the way of faded yearbook ephemera?

I shake off images of Teitelbaum bartending at the W Hotel when his European supermodel career doesn’t pan out; Vasquez teaching auto-body repair to reformed taggers at some trade school in a red state; Mason majoring in Undecided at a fancy New England finishing school, reading Hannah Arendt for fun and pretending to be poor, wearing the same ripped sweat shirt that he’s got on right now.

Perhaps I shouldn’t worry so much. The boys are refreshingly hopeful about the future, spinning pragmatic, practical premonitions of their adult lives to come. Mason, ?for example, predicts that the Wiggers will all get office jobs, families and clothes that finally fit them.

As for the Indie Fucks?

“We’ll be fine,” Mason half-laughs, gently assuaging my fears as he affixes his iPod earphones atop his head and pumps the volume way up on his favorite Bright Eyes song. “We’ll eventually all become semi-happy, semi-alcoholic divorcées like all our hippie parents knew they eventually would.”

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