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Former skate pro Tommy Guerrero now leads a "pretty cool" life as a businessman and a musician.

By A.C. Thompson

TOMMY GUERRERO WAS a teenage skate god in the mid 1980s. Unlike the mile-long list of child stars who went on to become Grade A fuckups – like the entire cast of Diff'rent Strokes, for example, or former skate hero Christian Hosoi, currently serving a five-year-and-ten-month sentence in the federal pen on a drug rap – he is alive and well adjusted today.

In the mid '80s the scrawny San Francisco kid with a face full of crooked teeth rode for the best team of the era, shut down rival pros at contests, had his picture splashed across the pages of the skate mags, and circled the globe doing demos and autograph signings.

These days he's a 35-year-old office dude with a cubicle, an ergonomic chair, and Clark Kent glasses.

There are worse fates. The corporate gig is cool: He's an exec at Deluxe, one of the most successful skateboard companies in the world, in which he holds an ownership stake. And his typical grind isn't so grinding. He strolls into the company's Hunters Point headquarters at 10 in the morning, works with his buddies, and knocks off by 4 p.m.

Sure, he's got a few gripes. He wishes he'd been able to skate competitively a little longer. He pops ibuprofen to dull the aches of his battered spine. But for the most part, Tommy's transition from extreme-sports deity to regular joe has been graceful. That's an accomplishment, considering.

He's also picked up a second job. Most nights you can find him in his home studio, strumming guitars, programming beats, tweaking samples, and generally geeking out. Since 1995 he's channeled his relentless energy into a string of engaging, cinematic post-hip-hop recordings, including two solo records for the über-chic Mo' Wax imprint.

By indie standards, the Mo' Wax discs have done respectably, if not spectacularly, selling around 40,000 copies. "My first dream was to become a professional skateboarder, and it happened," Tommy says, lounging in a faded leather chair as afternoon sun filters into his west Oakland warehouse. "My second dream was to become a musician, and it's happening. Not that I'm going to get huge or anything. I've already achieved more musically than I ever thought I would. That's pretty cool."

All in the family

Tony Guerrero, Tommy's older brother by three years, got hooked on skateboarding in 1975. He was a regular at the pay-to-ride concrete skate parks that ringed San Francisco at the time.

Tommy was anxious to try out his big brother's board, a thick slab of pine with brittle clay wheels. One day before Tony got home from school, Tommy took the board for a roll. One of the wheels came loose, and ball bearings spilled out all over the street.

Tony went ballistic. Most siblings have rivalries; the Guerrero brothers had armed conflict. "I was so pissed off, I chased him around the block," Tony says, laughing. "I was gonna pummel him."

A year later the two boys were both trying out for a local skate team. "Tommy was nine years old at the time, and he did his little freestyle routine, and he was really good," says Bryce Kanights, a former photo editor of Thrasher skate mag. But only one of the Guerrero kids was selected for the team – and it wasn't Tommy. "Tommy went home bawling; he was so upset he didn't make the team," Kanights says.

Skateboarding came to dominate Tommy's childhood. "I always felt different," Tommy says. "That's what I think drew me to skateboarding. The independence. The freedom. You didn't need anybody else to do it."

When punk rock blew up in the late 1970s, it quickly became the soundtrack to Tommy and Tony's lives. Outsiders, they gravitated to the raging San Francisco punk scene, turning up at now defunct nightclubs like the Mabuhay Gardens, the Tool and Die, and the Stone to catch hometown nihilists such as the Lewd, Sick Pleasure, and Code of Honor.

Despite the fraternal bloodletting, Tony convinced Tommy to start a band with him. They went through a series of names before settling on the moniker Free Beer, which was pretty funny since Tommy, the bassist, was barely five feet tall and obviously underage. There weren't a lot of all-ages venues in those days, and there's an oft-repeated, possibly apocryphal tale about little Tommy being smuggled into the Mab in a drum case. Between 1981 and 1983, Free Beer gigged with DOA, Dead Kennedys, Black Flag, Bad Religion, the Dickies, and other three-chord heavyweights, releasing some songs on compilation records.

Life at home – a succession of apartments, most of them in the Sunset District – wasn't always Leave It to Beaver. Dad was AWOL. He'd taken off when Tommy was six months old. Mom, a secretary for the U.S. Department of Health and Human Services, sometimes struggled to provide for the boys.

At one point the family was jammed into a two-bedroom flat with six other people: two cousins, aunt and uncle, grandma and grandpa. "We just slept wherever we could – the living room, the couch, wherever," Tony recalls.

Concrete jungle gym

By 10th grade Tommy was done with school. On paper he was enrolled in MacAteer High School, a public institution near the West Portal neighborhood, but in reality Tommy rarely made it to class. His deviant aesthetic – spiked hair, spiked wristbands, and spray-painted T-shirts – earned him endless shit from his classmates. You gotta understand – punk rock wasn't yet in heavy rotation on MTV. Says Tommy, "I just could not deal with school, could not deal with the teachers, the students, the system. I started fucking off, cutting school. I'd go skating all day, every day. My mom was at work all day. She didn't know what was going on."

No adult could've seen his decision as a great career move. Skateboarding in the early '80s wasn't the massive, X Games-fueled $1.4 billion industry it is now. In fact, the sport was going through convulsions. Waning sales had killed most of the skateboard companies, and surging insurance costs had shuttered nearly all of the skate parks.

While Tommy's peers stayed in school, followed orders, and stuffed themselves into tidy cookie-cutter lives, he followed his instincts – and they led him to the streets.

With nowhere else to ride, he turned the city into his playground. He bombed hills, ripping down Ninth Avenue toward the park, adapting skate-park maneuvers to the urban infrastructure – grinding curbs, launching off benches, carving concrete drainage ditches, and generally abusing any hard surface he could find.

When Thrasher and the rest of the skate zines began hyping Tommy and other city riders, urban skating took off. And when skaters began organizing street contests, Tommy stomped the competition. Former pro skateboarder Rob Roskopp, who was on the Santa Cruz team, remembers Tommy as "this little kid from San Francisco who took everyone by surprise when he won the first street-style contest in 1983. He had a flowing style that won over everyone."

Skateboard legend Stacy Peralta was intrigued by the street-skating phenomenon. Presciently, he saw it as the future of the art form: not many kids had access to ramps or the few remaining skate parks, but they all had plenty of asphalt to play with.

In 1984 he signed Tommy to a contract with his company, Powell Peralta skateboards, making Tommy the first professional street skater in the history of the sport. "A lot of the vertical riders on my team were really angry at me for doing it, because they thought I was manipulating the sport," says Peralta, who now directs films for a living. "That was a demarcation point in skateboarding. When I was a kid growing up skateboarding, the only other people you saw skateboarding were white, blond-haired surfer kids. Now it's completely left its surfer roots in the dust, and it's become a hardcore urban sport, and guys like Tommy and [Steve] Caballero were right on the crossroads of that – especially Tommy, because he was a street kid."

As skating rebounded and board sales surged, Peralta flew Tommy and the rest of his team – Caballero, Tony Hawk, Rodney Mullen, Mike McGill, Lance Mountain – to contests and demos around the globe and shot a series of enormously popular videos with the squad. They were the most influential riders of the decade, and teens worshiped them as if they were rock stars.

At 19, Tommy was pulling down $70,000 a year, huge money for a teenager, and spending the bulk of his time on the road. He made $500 a day teaching actor Christian Slater to skateboard for the Hollywood bomb Gleaming the Cube. The kid who never had his own bedroom while growing up bought a three-bedroom condo in San Francisco, a home he rarely saw, owing to his touring schedule.

For many young Latinos, Tommy became something of an icon – simply by being a visible, talented Latino at a time when brown folks were almost completely ignored by the mainstream media, Hollywood, and the music industry.

In 1990, Tommy bailed on Powell Peralta. Burned out, Peralta, the spiritual leader of the team, was leaving the company. Hawk and Mountain were both splitting to start their own skate businesses. For Tommy, it looked like a good time to cut. He hooked up with buddy Jim Thiebaud and founded Real Skateboards as a division of the Deluxe empire, which is now a 30-employee corporation whose product lines include Thunder trucks, Spitfire wheels, Anti-Hero decks, and Forties clothing. During his early days as an entrepreneur, as he worked to get the fledgling company off the ground, Tommy earned only a third of what he'd made with Powell Peralta.

His body had taken a beating, too, though for a devotee of an invariably body-damaging pastime, Tommy suffered surprisingly few debilitating slams. But eventually, it was time to make room for his company's young guns; Tommy took his final bow as a pro in 1995.

Instrumental groove affair

An ancient thrift store-scored skateboard sits on a bowed shelf over Tommy's couch. Otherwise, there's little to indicate that a skater might live here. Most of the space in this cinder-block warehouse is given over to Tommy's current passion.

Strewn across the room are a six-by-six shelving unit filled with vinyl (including about a million Herbie Hancock records), a rack of samplers and synths, an Apple computer loaded up with the Pro Tools music-mixing program, a worn black Fender bass, a crate full of cords, a four-track mixing board, a DAT machine, and a bunch of mics.

The sounds that come out of all this gear might be described like this: Dusk is settling on Mission Street as you walk toward the 16th Street BART station. A grizzled wino is plucking out sad, vaguely Spanish notes on a guitar. Two Samoan guys clad head to toe in immaculate Fubu gear are bumping Tupac on a boom box. As the sounds mingle, dope fiends search for chemical salvation, immigrant moms push their strollers, hipsters head for their hipster hangouts, police stand around impotent, and all the while Tommy lurks in the shadows with a mic, recording the scene.

Put less abstractly, the records are jazzy instrumental groove affairs, with Tommy writing, arranging, playing most of the instruments, and capturing it all with low-tech four-track recording gear. On one number a cool organ riff that calls to mind blue-period Coltrane lies over pneumatic Tribe Called Quest-like beats, as guitar blurbs swirl and move in and out of the mix. On another track the rhythm disintegrates, with beats scattering all over the place, free jazz-style, before a thick, incessant bass line takes over and provides the meter.

Not everybody is sold on the aesthetic. A few critics panned his two Mo' Wax discs, 2000's A Little Bit of Something and the more recent Junk Collector EP, as flat and self-indulgent. One compared his foray into music to Michael Jordan's ill-fated attempt to play baseball. Another, a reviewer for Pitchfork Media, an online mag, harshed on A Little Bit as "lacking," "generic," "lame," and "boring."

Tommy admits the bad reviews get under his skin. "Those are the only ones I remember," he says.

Fear of critical rejection hasn't curbed his prolific creative output, however. In the past two years he's cranked out an LP and three 12-inches with San Francisco's DJ Gadget, a solo 45, a solo EP, and an LP with the band Jet Black Crayon, and at this moment he's frantically writing and recording another 14-song disc for Mo' Wax.

Lying at the center of this stack of recordings – which this writer happens to consider brilliant-is a melancholy vibe. I ask him about it, and we talk about fractured hearts and tragic deaths, and I start to think that perhaps Tommy's blue mood music is actually a metastasized form of punk rock: the adolescent anger of punk rock filtered through the cell-transforming experiences of adulthood. And his one-person recording studio seems like an extension of the rush of independence he once got on a skateboard.

"I don't want to work in an office forever," he says. "No way. I want to make music all day and go skating with my friends at night. That's what I want."

If the past is an indication, he might get his way.