Trick Daddy broke the internet before many rappers even knew what it was.

Back in September 1998, when computers crawled the ’net on 56k modems and America Online was spam mailing internet trial CDs to addresses around the U.S., Trick Daddy released his gold-selling sophomore album www. thug. com, the first notable LP themed around the World Wide Web.

The cyberspace concept was prescient during an era when barely 40 percent of households had internet access, according to the August 2000 U.S. census—and less than one in four black homes were logged on. But Trick, who went to prison in 1991 on drug and weapon charges, saw the still-inflating dot-com bubble as a chance to capitalize on the future.

“I noticed a lot of things in prison was based on computers,” the 43-year-old rapper tells Genius. “It was the simplest things: your [inmate identification] number, cell number, jail number. My mom got her food stamps based on the last number of her social. Then with video games—Nintendo and Atari—everything was computerized.”

Fresh off his modest 1997 debut LP Based On A True Story (released under the name Trick Daddy Dollars), Trick had built a buzz in his hometown Miami by showing his city’s gutter side—not 2 Live Crew’s booty-shaking music that had previously defined the region. He was the flagship artist of Ted Lucas’ upstart Slip-N-Slide Records, which had a ragtag staff of six people who each performed multiple jobs. Trick was known for dropping ideas on the label’s brass after leaving the club at 4 a.m. “You have to answer the phone, because he might forget that idea by 10 or 11 o’clock,” remembers Lucas, who was initially perplexed by Trick’s early morning internet concept pitch. Trick adds, “I was telling Ted we need to do something to take advantage of what’s going to take over and rule the world.”

Trick’s sophomore album was about 30 percent complete when he introduced his forward-thinking title and theme—the breakout single and Trina introduction “Nann Nigga” hadn’t even been recorded yet. But still, the concept of the internet is seldom reflected in the lyrics. Another early adopter, Slip-N-Slide artist Marcus “Society” Effinger, used computerized voice interludes—more Stephen Hawking than A Tribe Called Quest’s Midnight Marauders host—to push the agenda. The intro “Log On,” states “Welcome, you are now online at www. thug. com. This site is strictly for the thugs.” The outro, “Log Off,” drops garbled web jargon in the same voice:

This is the first second of the last minute of the first hour of the last day of this millennium. You have successfully completed all sequences located at the site www. thug. com. Online access will disconnect in T-minus three seconds: 3, 2, 1.

“We had voice recognition software, the first level of that—everything had that same computer voice sound at that time,” Society says. He regrets not pushing www. thug. com’s internet theme further musically, a la future concept albums like Childish Gambino’s 2013 LP Because The Internet.

Society—who raps, “That’s why I stay calm like www dot” on album cut “Living in a World”—did his part in incorporating the internet theme. A former graffiti writer then studying graphic design and website building, the Bronx-born artist designed www. thug. com’s cover based on the very first iMac’s homepage from 1998. The image—a perennial entry on “worst album cover” listicles—shows Trick Daddy’s bald head and logo, both surrounded by a green, horror-movie glow atop a cloudy sky backdrop. The top border reads “Thugscape”—a play on vintage web browser Netscape Navigator—while the bottom scroll bar reads “you are now ‘on-line.’”

Names of Slip-N-Slide artists like Tre+6 and The Lost Tribe grace the “buttons” on the bottom of the artwork. The label’s general manager Debbie Bennett came up with the navigational toolbar that spans the cover’s top panel—“Music,” “Sex,” “Drugs,” “Money,” “Death”—after noticing the recurring themes in Trick Daddy’s music. “Knowing he didn’t expect to live a long life,” Bennett says, “I would literally look for him on the news at night to make sure he didn’t do anything bad. Because he came from such a lifestyle.”

Despite embracing an ahead-of-the-curve concept, Trick Daddy had to catch up in some ways. When www. thug. com dropped on Sept. 22, 1998, Slip-N-Slide didn’t even think to buy the domain name. They finally purchased it in 1999—Lucas remembers interviewers badgering Trick to do so. The move helped Trick corner the “thug” brand long associated with 2Pac (Trick Daddy’s six subsequent album titles includes the word). Initially designed to mirror its namesake LP cover, thug.com served as Trick Daddy’s homepage until 2014, when it began redirecting to Slip-N-Slide Records’ site due to lack of updates.

“If I knew what I knew now, it would’ve been Worldstar back then,” Lucas says in retrospect, imagining an additional revenue stream for Trick. He’s received offers to sell the iconic domain name, but says none were substantial. “I probably would’ve considered it to be whatever information goes on in the rap world. Stuff you don’t get every day. Stuff that was gangsta, stuff that was dangerous. Interviewing people in jail that were artists and getting their point of view.”

“We bought that domain name, without realizing how valuable it could be one day,” Trick adds. “We played around and procrastinated for two decades. Now, people are making hundreds of millions—if not billions—of dollars off the same thing that I had already envisioned in ’95.”

Despite some missed opportunities, www. thug. com was ahead of its time. And other artists followed Trick’s lead in embracing the World Wide Web. In July 1999, Public Enemy—the legendary crew that initially discovered Society—flipped the traditional music distribution format by releasing There’s A Poison Goin' On online via free MP3 download.

“And to think it came from a rapper,” Bennett says of Trick Daddy. “It wasn’t Led Zeppelin. It wasn’t Blink-182. It’s a rapper that had this vision. I’m very proud of him in that. A lot of us see, one, two, three, four, five—[Trick] has a tendency to see one to 20.”

As for Trick Daddy—who was dragged on social media in October for comments that many thought were sexist and racist—he misses the days when the internet wasn’t such a big deal.

“I didn’t think it would invade our privacy, or take over television, control our kids and our women. The internet controls society,” he says. “Whatever a person does or says on the internet, is taken very seriously when it shouldn’t be. I never imagined for something so powerful to have the potential of being so disruptive.”

The internet stops for no one—even for a rapper who was years ahead.