THERE'S A LINE FROM A SONG ON STEW'S NEW ALBUM, The Naked Dutch Painter . . . and Other Songs, that brought me up short on a first listen with its tough-tender specificity about L.A. life, and love lost therein, that I'd not heard invoked since the heyday of Randy Newman. “Adams and Crenshaw is beautiful/And we're smiling in the sun,” Stew sings, his robust voice improbably set in the middle of delicate, dreamy piano. I felt an aha at the mere mention of that corner, a rivers-deep satisfaction I haven't ascribed to any music of the day, and certainly not to aging Adams and Crenshaw, in a long, long time. After another listen, I don't know if the song is sarcastic or nostalgic, but that doesn't matter; what's important is that Stew elected to sing about it.

When we meet for an interview at a Pasadena diner, I mention the line, which is from a triptych of songs called “The Drug Suite.” Stew looks at me, amazed. “Wow,” he says. “That's my favorite line in the album. It isn't ironic. When I was 10 or 12, that place was magical for me. That was near my church where I sang choir, and my favorite taco stand. It was near that roller-coaster hill on Arlington, you know it?” Indeed I do. He seems genuinely happy that I corroborate the childhood lure of a little-known L.A. crossroads, though the more perverse side of him likes the idea that maybe I got it wrong. Despite a reputation as a social critic, Stew claims not to do conscious irony in his music — but he doesn't mind if you think so, or if you think anything about his music that hasn't occurred to him yet. “It's like playing a game,” he says with a faintly devilish grin. “You might think I'm being ironic at times. But I'm not. That's the joke — that there isn't one.”

Not that time, but as Stew (born Mark Stewart) and a host of critics and admirers will tell you, humor — if not irony — at its most bracing and unexpectedly resonant is what separates him from the traditionally touchy-feely singer-songwriter pack, and what has made Stew's band The Negro Problem so delightfully unclassifiable since it launched its first album, the wickedly titled Post Minstrel Syndrome, five years ago. Front man Stew, 40, has in recent years gone solo; Painter is his second effort, a follow-up to 1999's Guest Host. Ironically — or not — Stew has described these albums and their self-contained stories as outlets for his sensitive side, a countervailing force to the infectious beats and lyrical impudence The Negro Problem has worn on its sleeve throughout its seven-year history. He calls The Naked Dutch Painter, which was recorded live at the Knitting Factory for that intimate feel but also improved upon in the studio, his first work “with a life of its own.” Certainly tunes like “The Drug Suite,” “Giselle” and “Love Coming Through the Door” are as up-close and personal as Stew has gotten, though that hardly means he's lost his edge or sense of humor in the process. (“Cast your last into her well,” goes “Giselle.” “She wears leather/whatever the weather.”) However large or small the scale, in fact, Stew's talent for panoramic observation and a converse gift for telling detail are always in abundant evidence, solo or no, and The Naked Dutch Painter is no exception. Stew nonetheless likes to separate things in his own head. “The Negro Problem is like having a party, and the solo records are like writing a letter,” he explains over pancakes. “I wouldn't tell the 'Naked Dutch Painter' story at a party, but I would tell it in a letter.”

The first line of the album's title song is a shocker, even by Stew standards, that seems indeed best read in private: “The naked Dutch painter in the kitchen does not want to fuck you.” But the song swiftly gets beyond the sting of the F word to poignantly address a host of things that have become Stew calling cards: stunted ambition, unrequited affections, emotional façades with a decidedly L.A. sheen. And race. (“She's asking questions about my groovy black ghetto,” Stew sings tartly of the über-hip Dutch painter.) Oddly, Stew and The Negro Problem rarely get probing questions from interviewers about race beyond an obvious comment on their name, though it's not so odd considering a general skittishness, even among music critics, about addressing the dysfunctional relationship pop music has long had with black musicians, who have always been more strictly categorized than any other group. “I get the 'hmmm' thing of a black guy playing white music — how's that feel?” muses Stew, who cites his biggest musical influences as James Brown and the Beatles. “That clearly reflects a narrowness in thinking, because all musicians grab from different areas. The question implies that your mind isn't big enough to accommodate everything. White critics will say, 'This is strange, this isn't what black music is.'” What black music is is another article, but suffice it to say that race is as consistently but unselfconsciously present in Stew's music as love and heartbreak and absurdism; sometimes they all converge, though never for the sake of protest or point making.

Which isn't to say that Stew doesn't get angry, as some critics have patronizingly implied in casting him as the philosophical and literate black artist who therefore cannot be angry, at least not in the way black anger is popularly understood. Stew stews plenty on Naked Dutch Painter, in the title song and elsewhere, but he does it within the framework of story, and counters the heat with the float-away hypnoticism of “Reeling,” the bluesy meditation of “Cold Parade,” the sly musings of “Single Woman Sitting.” This is also the mark of The Negro Problem, which in songs like “Heidigger in Harlem,” “Buzzing” and the evocative “Comikbuchland” offers the most pungent and layered disquisitions about blackness and identity this side of the Sepulveda Pass. (Stew, for the record, grew up in midtown and has lived on both sides.) Stew's TNP bandmate and co-producer Heidi Rodewald credits the complexity of the work to simple juxtaposition — the often jarring contrast between words and melody, à la Randy Newman. Stew agrees and, like Newman, believes that rap, that presumed bastion of unsubtlety and black anger, is the most inventive pop music going these days — besides his own.

“I don't listen to it all, but it requires certain elements that make it art, whether you admit to it or not,” he says. “Lyrically, those guys have got to be on their game. Rhyming takes work. Nor do I believe that the guy in the song really wants to slap up his bitch. To me, it's just funny. Maybe he does, but the bottom line is, I really have no idea what Master P is thinking.”

AFTER THE GODFATHER OF SOUL AND THE FAB FOUR, Stew's brightest guiding lights were not musicians, but comedians; Richard Pryor was something of a god. (“I must have listened to That Nigger's Crazy a hundred times when I was a kid.”) He calls In Living Color alum David Alan Grier “way ahead of his time — he was a black middle-class guy who was as funny as hell! He was talking to me.” Stew's greatest fantasy of the moment is to publish a humor journal geared to the black middle class that addresses the usual grave issues of the race, but with a certain irreverence — a tension of words and melody that certainly nobody's tackled yet. “It would be a Monty Python approach to the Underground Railroad,” Stew says brightly. “To me, laughing at it isn't wrong, it's revolutionary. Black history itself is so deadly serious. We have to bring it to popular culture, to the masses, to make them aware. It's the only way to make people listen.” It's a radical approach, playing both ends against an unexplored middle, that has worked to poetic effect in his music, wringing heart from hard truth, beauty from cooked curls, joy from concern.

“The nightmare and the perfect situation for me is, your grandmother hears my stuff and is scandalized by the words,” says Stew, “but later she says, 'That sure was a good tune.' That's great.”

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