The grand tour of Darren Harper’s old neighborhood in Southeast Washington is nearly complete. There’s the spot where he sold his first piece of crack at age 10, for five bucks. The sidewalk where he saw a man bleed to death from a gunshot wound to the neck. The house where his cousin shot his stepfather after the latter raised his hand to Darren’s mother. The sidewalk where Darren, in his late teens, had a shootout with his partner over a deal gone bad. The corner where Darren, in a rare moment of carelessness, was nabbed by police and caught a cocaine distribution charge.

The tour — no charge, no tips, no air-conditioned bus, no stuffy history lessons — is about to break up when Harper stops and says, “Hold up.” He points to the side of a rundown apartment building on Savannah Terrace SE. “That,” he says, “is where I found my first skateboard.”

Where the tour ends, the story of Darren Harper begins: hoodlum-turned-skateboarding-star. A born hustler who left one cutthroat game for another, and used the same attributes — street-smarts and charm and relentlessness — to find success in both.

“One thing I’ve always had, no matter what I’m doing,” he says with a smile, “is hustle.”

And it’s also the story — with Harper, now 29 years old, in the starring role — of skateboarding in D.C., the rougher, edgier cousin to the more polished, familiar California style. This strand of the story saw its zenith arrive over the weekend with the Maloof Money Cup, the biggest skateboarding event in District history, which, among other things, brought the construction of a permanent skate park alongside RFK Stadium. Harper was both the main local ambassador for the event and a competitor.

“You can’t talk about skateboarding in D.C.,” said Mark Waters, one of the event’s organizers, “without mentioning Darren.”

Jagged path to success

The Darren Harper story begins in the early 1990s, beside that apartment building, in a pile of belongings from an evicted family. Amidst this particular pile on this particular day was a bright yellow skateboard, which attracted the attention of little Darren, then around 10 years old. He rode it on his rear end at first, then his knees — rolling down the hill that led to Mississippi Avenue SE.

Eventually, that board — well not that exact board, but the ones to which he upgraded over the years, occasionally by theft, later by endorsement deals — would be his vehicle to escape the ’hood and a lifestyle that, he says, “was like digging my own grave.”

These days, Harper makes a living with his board, through some top-shelf endorsements of clothing and equipment companies, plus a side gig giving private lessons to suburban kids who worship Harper’s urban-ness and wish they could grow up to be half as hard. It’s not an easy living — he has no manager, agent or PR rep, and hustling his own deals is almost a full-time job — nor is it a lucrative one. But in this game, success is defined as not having to take a day job. And Harper hasn’t had one in about five years.

Getting from that point, the little kid with the little yellow toy skateboard, to this point was anything but simple. He may be a local legend and internationally recognized skater, a star of popular skate/rap videos on YouTube, or even an “urban cultural icon,” as top skater Felix Arguelles, Harper’s team leader with the Famous Stars and Straps clothing company, calls him. But instead of a linear path to this status, Harper’s darts from abysmal lows to stratospheric highs. And sometimes the path disappears altogether, for years at a time.

In the early days, after an adolescent Harper, bored of jumping over discarded refrigerators and truck tires in the neighborhood, discovered Freedom Plaza downtown, he would hide his hobby from friends, who ridiculed him for playing a “white boy’s sport.” Before catching the 32 bus downtown, he would stash his board in a black plastic bag, or disassemble it and cram the pieces into his bookbag, then reassemble it later.

Raw as he was, the young Harper had some promise. He had “pop” — the ability to get vertical clearance over obstacles. And at a time when skateboarding was beginning to absorb the urban ethic, with fresh-faced white kids from Orange County, Calif. imitating rappers with their baggy clothes and bling, Harper was the real thing.

“He was getting good,” says Chris Hall, a 1990s-era local skateboarding legend who would eventually mentor Harper. “And then, he disappeared for, like, two or three years.”

The family business

The teenaged Harper wanted to skate, but what he really wanted was the shoes — the Air Jordans, with that iconic silhouette of Michael Jordan in mid-air. He also wanted the cars and the jewelry and the girls. But especially the shoes. “As a young’un I would watch the dealers pumpin’,” Harper says in one of his skate/rap videos, “ ’cuz all I ever wanted was the shoes with the man jumpin’.”

Besides, his support system in the drug game was better and deeper. His dad, at least when he wasn’t in jail, was a dealer of some stature, as were a few cousins. Getting in the game was easy. Moving up the hierarchy was easy, too, once Harper, with his charm and hustle, proved to be such a natural. At one point, he says, he was pulling in $1,000 a day.

“I just came in, and people liked my style,” he says. “I was genuine. It’s like selling yourself, to get people to where they only wanted to deal with you.”

Harper worked in the daytime, which seemed safer. “I’d come in at 8 [a.m.], do my thing, and when it got dark I’d leave,” he says. “A lot of times, when I’d come back the next morning, so-and-so would be like, ‘You hear? So-and-so got killed last night.’ Or, ‘So-and-so got locked up.’ I think God was trying to guide me, because he knew I was supposed to be doing something else. I had too much talent.”

Deep down, Harper figured it was going to take something catastrophic to get him out of that game. He only hoped it didn’t involve him taking a bullet, or putting one in someone else. He was lucky that the beginning of the end for him came with nothing worse than a close call.

One night, as he was serving a client in his territory — a parking lot in a run-down strip mall on Naylor Road SE — the cops jumped out of the woods across the street. He already had beaten one distribution charge; he knew a second might mean serving serious time. As the cops swarmed, he juked his way out of their grip and scaled a 20-foot fence to get away. But they had clearly seen his face.

His father was recently dead of an overdose. His mother was hooked on crack — and while Darren had never provided her drugs , he understood his indirect role in feeding her addiction. One of his partners was dead, another was in jail and a third, just a few weeks before, had engaged Harper in a shootout, and was still looking to make trouble for him.

“The older hustlers always told me, ‘If you at war with somebody, you can’t be out here [on the streets] doing what you doing and not watching out,’ ” Harper says. “So I chilled out for a while.”

As he laid low, Harper went through some soul-searching. He was a talented visual artist, having earned scholarships to Duke Ellington School of the Arts in Northwest, and later, the Maryland College of Art and Design — though he withdrew after only a semester. He couldn’t imagine himself trying to make a living at that.

“What else are you good at?” his girlfriend asked one day.

“Well,” he said. “I used to skate.”

“Skate? You mean, rollerskate?”

“No,” he said. “Skateboarding.”

He started going back to Freedom Plaza, and the folks who remembered him as a kid were taken aback. He was still good, but now he had a grown man’s body — lean and wiry. Instead of imitating the white skaters he saw on Nickelodeon’s “Sk8 TV,” he was forging his own style, more raw and athletic. But he couldn’t completely leave his old game behind. He would sell drugs in the morning, and skate in the afternoon. And he would frequently bring the street mentality with him downtown, to disastrous effect.

One day, when a security guard was giving him trouble outside the IMF Building — a common occurrence for urban skaters — Harper beat the man so badly it sent him to the hospital. The next day, Harper was arrested. Though he faced a 30-year sentence, he pleaded down to probation, with anger management counseling and community service.

One day, in desperation, he told Hall, “You gotta help me save myself. Either I’m going to die, or I’m going to kill somebody.”

‘I’m the guy here’

Hall had a plan. He scrounged up enough money for a pro-quality camera and began compiling video of Harper on his board, handing it out to anyone who might have some pull. Finally, at a trade show in San Diego in 2006, they got an audience with Travis Barker, drummer for the rock band Blink-182, and a skateboard enthusiast who had started a clothing company, Famous Stars and Straps. Barker offered Harper an endorsement deal.

“Darren stands for the kid who hasn’t been handed anything, and has been able to stay out of trouble while coming from trouble,” says Arguelles. “He’s kind of the best at what he does, but his range of skating is maybe narrower than other people’s spectrum. He didn’t grow up going to skate parks.”

With rap having long ago replaced punk as the soundtrack of the skateboarding business, Harper isn’t above using his authenticity to his advantage. He always resisted the urge to pick up and move to California, the industry’s epicenter, not only because of family constraints — he has four kids by four different mothers (“You can put that in — I’m all about keeping it real,” he says of this fact) — but also because he understood the business dynamic.

“I’d get swallowed” in California, he says. “There’s a million skaters over there, and a lot of them are better than me. I mean, they grew up getting dropped off at the skate parks. ‘Here’s your lunch, honey! Pick you up at 5!’ I never had that.

“Maybe I’d be unique out there, and that would be cool. But I’m the guy here. I represent D.C. I don’t need to go out there. They can come to me.”

Harper is still hustling; only the product is himself. His story. His life. His street-ness. His Twitter page bills himself as “the Obama of Skateboarding in D.C.” He hopes to launch a clothing company called “Love Being Street.” He’s looking for funding for a documentary of his life. “My story should sell itself,” he says. “I’m the realest dude doing this.”

Over the years, he has had dreams in which he is killed. But lately, he dreams of grander things: A skateboarding mecca rising in D.C., with Darren Harper at its center, mentoring hundreds of kids who stood at the same crossroads he once did, and who could find their way to the right choice with his help.

“Darren is a blessing to this community,” said D.C. Ward 5 council member Harry Thomas, who has seen Harper hand out dozens of free skateboard shoes to kids from the gear Harper’s endorsers send him. “He’s a very positive force in the neighborhood.”

The tour of Harper’s neighborhood is now closed, but two more curious tourists come sauntering over: two boys, who look to be 13 or 14. One of them holds a long stick and drags it around idly. It’s late summer. There’s nothing to do. They see Harper posing for a photographer outside the strip mall on Naylor, and they ask, “Hey, who are you?”

“Who am I?” Darren Harper explodes. “Man, I helped make this place. You ask anybody here. Ask any of them drunks, any of them fiends. Ask them about ‘D.’ I represent the ’hood all day. Go up there and ask ’em about ‘D.’ They’ll tell you who the [expletive] I am.”

Harper turns so the kids can’t see his face, and there’s a wide, devilish grin on his face. Then he goes back to posing for the camera, and he puts the hard look back on his face. And the boy with the stick and the other boy walk away, looking for someone who can tell them who “D” is.