The imagery on these records would echo across rap’s landscape. “I could hear what other artists were doing when they were talking about this player, pimp image, the Cadillacs and the funky music,” Too Short says. “I knew where it was coming from. They told me. I saw it in Outkast. I saw it in Snoop Dogg. I saw it in UGK. It was clear. What I was doing was infectious.” The laconic, seen-it-all attitude would reverberate, too; you can hear its echoes in Jay-Z’s detached crime narratives, in Master P’s bass-heavy self-mythologization, in the granular focus of T.I., Young Jeezy and Gucci Mane’s drug-trade reflections. Even as he found national fame, Too Short kept his focus on Oakland, proving to everyone that the most hyperspecific regional references could, on record, feel universal. It’s a lesson rap has never forgotten — and only one among many it learned, in large part, from this rapper.

To understand Too Short’s influence, it’s useful to consider that he found national success at a moment when rap still seemed like it might head in a very different direction. As his records crept across the country, another Oakland rapper took off like a rocket. MC Hammer was Too Short’s opposite: glitzy, energetic and so family-friendly that he had his own Saturday-morning cartoon. For a moment in the early 1990s, Hammer became a crossover pop superstar. “I thought Hammer was the funniest thing in the world,” Too Short says, “but I never, not one day did I ever not respect him. I saw what he was doing. I thought it was funny, but I knew it was genius.” Onstage, Hammer wore glittering pants and led phalanxes of dancers. Too Short performed alongside just one other guy, an Oakland local nicknamed Too Clean, who was there mostly as an audience surrogate. “I hired Too Clean to be my hype man because he really just signified someone standing out on the street in Oakland who really liked Too Short,” the rapper says. “He can’t dance enough to be a dancer. He can’t talk enough to really be a hype man. But he’s perfect for what I need.”

The first time Too Short hit the road — in 1989, as the opening act for N.W.A. — some New York observers were shocked to see an artist with no profile on the East Coast getting huge reactions from crowds across the country. He had no radio hits, no sweaty live show. Other rappers, he says, would come to see how he managed it: “ ‘How do you rap with no fanfare? You can’t dance, you don’t do [expletive]!’” The reaction from the pop-rap duo Kid ’n Play, he says, was something like: “We out there jumping around! Shirt dripping! You walk out there, you like, ‘Biiiiiitch!’”

Hammer’s success, like Kid ’n Play’s, came and went. What the industry would rapidly learn in its aftermath is that rap’s great stars wouldn’t be smiling, dancing, family-friendly types. They would lie much closer to Too Short: gritty survivors who presented their power fantasies as cold, hard realism. At the dawn of the 1990s, there were “dirty” rappers who could sell millions — Too Short, Miami’s 2 Live Crew, Houston’s Geto Boys — but they never really seized the center of popular culture. By 1993, that had changed. Rap’s new megastar was one of Too Short’s old N.W.A. tourmates, another Funkadelic-obsessed Californian rapper and producer: Dr. Dre. More street-rap megastars would follow, including the bicoastal rivals 2Pac and The Notorious B.I.G. — both of whom loved Too Short, and each collaborated with him before their untimely deaths.

Too Short’s popularity was of a different sort. “He was like an old rock band,” Weiss says — “like R.E.M., getting in a van, building one album at a time.” Between 1989 and 1996, he released six albums, all of which went platinum. They proved especially popular in the Deep South — “the nonsophisticated markets in the country,” Weiss says, “not the cool people but the real folks.” Efforts were made to break the East Coast, but nothing ever made much of a dent. This failure didn’t bother Too Short: “I understand why they didn’t get it,” he says of New Yorkers. “A Wu-Tang, on the train, in your headphones, is getting you right where you need to be at to take that train ride, to get off that train, to deal with that city.” Lyrics about receiving oral sex in convertibles, he says, were “not going with the culture. I understand that, and it was OK.”