One summer night in 2007, local rapper Stackwell—aka Johnnie Walters Jr.—and his cousin Charles Chappelle pulled into a Union 76 gas station in South Seattle. A few minutes later, another car pulled up and a man named Deche Washington got out. For reasons that remain obscure, Washington began arguing with Chappelle. According to court documents, the two stepped around each other, fists raised. A woman who had arrived with Washington asked Stackwell—who was watching the altercation—why the two men were arguing. "[He] said he did not know," one court brief reported, "as he thought the men were friends." A few seconds later, Washington opened the front door of the car, pulled out a shotgun, and fired it into the air.

You can watch what happens next on jumpy security-camera footage posted to YouTube. This is what it looks like to me: Chappelle runs into the frame waving his arms and ducks behind a gas pump. Stackwell backs slowly and deliberately into the frame, carefully watching the action. Washington, holding his shotgun, chases Chappelle to his hiding place. Washington points the shotgun at Chappelle and suddenly jerks—Stackwell has shot him. Washington turns, stumbles, drops his shotgun, and runs out of the frame. Stackwell chases, firing his handgun, then jumps in his car with Chappelle and peels out. Police later found one spent shotgun shell and 15 handgun casings at the scene.

Washington was shot in the groin, lived, and served 36 months. Stackwell, on the other hand, was sentenced to 198 months—almost 17 years—for the shooting and illegal possession of a firearm.

"I had to pay $20,000 for [Washington's] doctor bills," Stackwell chuckled in a phone interview from Coyote Ridge medium- security prison. "I heard he went and bought a Cadillac."

Stackwell's sentence is so high, in part, because he had been convicted of prior felonies, including a firearm offense when he should've been in 12th grade. (He only made it through seventh grade, he says, and was basically on his own after that—which, in part, accounts for his criminal history.) His attorneys are appealing the case on grounds of self-defense and say the main witness against Stackwell, the woman who asked him why Washington and Chappelle were arguing in the first place, was threatened by Seattle police detective Shandy Cobane (who later became infamous for threatening—on camera—to "beat the Mexican piss" out of a suspect who turned out to be innocent).

Despite all the tough luck and dubious choices that have landed him in prison, Stackwell doesn't sound bitter in the slightest. His voice is eager and jovial, he laughs easily, and he says that while he's watched the idleness of prison curdle and harden some fellow inmates, he's been opening up and studying things, from prison-yard Spanish to the writings of Sun Tzu.

More importantly, he's been making music with the help of the prison's music studio, when it's available (plus a few "underground" techniques he declined to describe), and with aid from friends on the outside, including DJ Roc'Phella, producer Illoquint, and promoter Keith "Ghetto President" Asphy. Typically, he records vocal tracks and mails them to friends who elaborate on them with beats and production. Some tracks on his record S.T.A.C.K.W.E.L.L. sound rough, as if they'd been recorded over a telephone, while others sound as smooth as a studio recording. "There's ways to keep fresh material for the streets," he wrote in one letter. "A stepper gotta keep steppin'!"

Stackwell says he's been dabbling in music on the street, at house parties, and in clubs throughout the Northwest for years. "The only problem I had was I didn't see the benefit of recording it," he said. But prison has given him time—lots of time—to sharpen his craft.

The production on S.T.A.C.K.W.E.L.L. is filled with the light, glistening sound of hiphop records you'd buy on the sidewalk or hear on local radio stations across the country—shimmering keys, synthesizer-made strings, and the occasional loping rhythm of Southern hiphop. His lyrics dive back and forth across the longstanding dichotomy between "gangsta rap" and "conscious hiphop," ranging from criminal boasts to introspection. "I want everyone to be able to relate to me," he said. "You got to have empathy, to say I've done this, I've been there."

That street story casts a large, looming shadow in some of his songs. From "I'm a Pimp":

'Cause I'm a pimp!/Nigga, P-I-M-P/So c'mon, my nigga, break a bitch with me/'Cause I'm a pimp!/Nigga, I'm international/That means everywhere I go, I get cash from hos... She knows I'm her only friend, along with her only family/That's why when I say, "Get it, bitch!" she understands me/And no matter how I treat her, man, she knows she's my boo/...She do what she do.

I've known folks who've worked in street outreach programs with young prostitutes—who've dealt with the searing sorrow of that punishing life—and verses like this one could inspire a young social worker to burrow through concrete and strangle a pimp with her bare hands. But Stackwell argues he's not glorifying the hustling life so much as depicting it, as it was, while he was there. "I have a street story," he said. "But that doesn't mean it's what I'm involved in right now... Denzel Washington plays Frank Lucas [the infamous heroin boss in American Gangster], but that doesn't make him a drug dealer." Some of his other tracks, such as "Please God," are more forward-looking and reflective: "The game will confuse you, if you don't learn to take control/And see the dirt that we're doin's only diggin' a hole."

Stackwell's story isn't unique. Prison, and the whole damn world, is full of people wrestling with—and indulging—their angels and devils. But as a working artist behind bars, Stackwell is in an unusually stark position to articulate what it's like to be stuck with your past and groping toward an unwritten future.

Stackwell keeps up as best as he can with Northwest hiphop on the outside—he talks admiringly about Macklemore and his recent single "Same Love" about marriage equality. "Lots of dudes in here are talking about him," he said. "They say he's gay because he's advocating for whoever. But I think that's hella funny because there's something wrong with those guys! These straight dudes are talking about him, but they're not doing nothing! He's going around the world, becoming a fixture for the 206, and I'm supportive about whatever he's got going on."

If Stackwell has his way, he'll become a fixture for the 206, as well. "If they open up this gate for me," he wrote, "the game's in trouble, Brendan!" He's trying his damndest, even while the gate stays closed. Promoter Asphy said he has dozens of clients, but Stackwell has done more from behind the walls than any artist he's ever known: "He's getting more exposure and making more moves from in there than a lot of cats that are walking around free."

Stackwell chalks that up to the fact that he's taken on his prison time not as a long stretch of idleness, but as a chance to shed the distractions of the outside world and focus on what matters. "There are different forms of freedom," he said over the phone. "You got a lot of people out there who've got jobs and go home to their kids, but they're not free. Freedom is 95 percent mental. Yeah, I'd like to go out there to drive a car or go to the store or whatever. But when I do my music, I feel free!"