The 2006 Youth UpRising Christmas party featured healthy helpings of fried chicken, greens, and mac and cheese. That was certainly part of the appeal for the several hundred young people in attendance, the majority of whom were low-income and could be considered at risk of falling into lives of drugs or violence. But to their delight, the party also boasted a contingent of ghetto celebrities, including the head of a hip-hop record label founded by the late Mac Dre and the popular rappers E-40 and Mistah F.A.B.

Turf-identified rappers seldom interact directly with fans or involve themselves in community affairs — actions seemingly at odds with their hypermasculine public images. But that's just what happened on December 22. President J. Diggs of Thizz Entertainment donated shoes, warm coats, T-shirts, and PlayStation IIIs to needy youngsters. He even went so far as to disassociate himself from "thizzing," street slang for using the drug Ecstasy.

But the afternoon's biggest surprise came when Todd Shaw — aka Too $hort, the most iconic Oakland rapper of all time — announced that he was moving back to "tha town" and joining the two-year-old East Oakland community center as a career counselor. $hort's remarks were met with cheers, and attracted favorable notice from San Francisco Chronicle columnist Chip Johnson four days later — yet also drew pointed criticism from one of Youth UpRising's most outspoken opponents.

On January 20, Charles Pine of the anticrime group Oakland Residents for Peaceful Neighborhoods posted criticism on its Web site, and made his views known to members of the city council. Under the headline "Listen, Oakland Officials, to National Debate Over Rap," he complained that Youth UpRising was receiving city funds while working with rap artists who irresponsibly "promote sideshow culture" — an allusion to the outlawed ghetto gatherings known as sideshows. Pine called the participation of Youth UpRising dance groups in rap videos, and the nonprofit's teaching of music- and video-production skills "a modernized form of poverty pimping" unlikely to produce much in the way of long-term employment. Finally, he called Too $hort an unacceptable role model due to his frequent use of the word "bitch" and his promotional relationship with Remy Martin cognac.

It certainly wasn't the first time Shaw's persona turned out to be both blessing and curse. Too $hort had brought him fame, fortune, and a loyal, multigenerational fan base. It also has defined him rather narrowly. Despite Shaw's significant musical accomplishments, many can't get past his signature phrase — biiiiaaaatch! — and the way he draws out its syllables in a way that seems to boost its offensiveness.

Still, the rapper has few regrets. Like Frank Sinatra, he's a legend who has done things his way. Now 41 and graying, he has had one of the longest and most prolific careers in the hip-hop game. In the early '80s, when rap first spread from New York to California, Shaw immediately gravitated toward the new sound, performing at house parties and adopting his now-ubiquitous alter ego.

As $ir Too $hort, he began making personalized tapes for pimps and dope dealers in the hardcore ghettos of East Oakland, later selling homemade cassettes on the 43 bus line or "out the trunk" of his car. As word spread, a local label put out three solo $hort albums, Don't Stop Rappin', Players, and Raw, Uncut, and X-Rated, which quickly became de facto soundtracks for the Oakland streets. $hort's topics ranged from on-the-spot reportage about the then-burgeoning crack epidemic in "Girl (That's Your Life)" to puerile yet humorous discourses on fellatio in "Blowjob Betty." A falling-out with the label led him to launch his own Dangerous Music label, which released the now-classic Born to Mack in 1987.

Though now clichéd, Born to Mack's fables seemed fresh at the time. While bearing stylistic influence from Run-DMC, LL Cool J, and Eric B. & Rakim, the album took hip-hop in an entirely new direction. Scandalously risqué and unabashedly ghetto, it drew its inspiration not from the usual Bronx tales but California lifestyles. Its best-known song, "Freaky Tales," established a template for what would become the "West Coast" rap sound: slow and funky, with an emphasis on heavy bass.

But more notoriously, $hort strived to make pimping cool, portraying himself as an inner-city cartoon character whose dirty mouth and clever rhymes made him irresistible to women. This was the Record Your Parents Didn't Want You to Hear, though by today's standards, and partly due to its influence, its lyrics no longer shock:

I met this girl, her name was Joan

She loved the way I rocked upon the microphone

When I met Joan, I took her home

She was just like a doggy all up on my bone

I met another girl, her name was Ann

All she wanted was to freak with a man

When I met Ann, I shook her hand