Paul Middleton / Guapdad 4000

You can learn a lot about Guapdad 4000 from the events of June 15, 2019. On that day, he honored his NBA Finals wager with Drake by walking out on the Bay Bridge dressed in a raptor costume and holding a sign acknowledging that Kawhi Leonard (and Drake) had defeated his hometown Warriors. Hours later, he uploaded a reaction video of his mother watching him receive unsimulated fellatio in his “Flossin” music video. “This boy is crazy,” she said. “I’mma beat his ass.”

On the one hand, Guapdad 4000 is a rapper. He released his debut album Dior Deposits in late October; in between features from names like Tory Lanez, E-40, and Charlie Wilson, his velvety rasp of a voice skims pillowy production that sublimates Oakland’s signature low-end bounce amidst House of Balloons-esque atmospherics. This summer, he quietly stole moments on Dreamville’s compilation Revenge of the Dreamers III, like the chorus of “Don’t Hit Me Right Now,” where he gently sings “aye, I got the chopper” as if rocking a baby to sleep.

On the other hand, Guapdad is much more than a rapper — he’s a fully-formed internet personality whose absurdist social media videos were going viral on a semi-regular basis well before he released his first solo mixtape. In 2017, he went viral for confessing that he’s an anime addict who is “sexually attracted to tacos.” In 2016, on his 24th birthday, he declared that he would “not [be] tolerating anything broke this year” as $100 bills rained down on him and the Pokémon theme blared in the background. If you dive into the recesses of Tumblr, you might unearth an old clip in which he walks naked into a West Oakland Chinese restaurant and orders egg rolls.

Paul Middleton / Guapdad 4000

Guapdad was a fixture of the East Bay party and arts scene early in his career. After high school, he earned his associate degree in fine arts at Berkeley City College, and he rapped and produced as YB Keem in a six-person collective called The Whybees. They earned income by promoting and throwing parties until police started cracking down on their events. Recording funds dwindled, and their momentum sputtered. “Life just started setting in, we were getting older,” he tells Highsnobiety over the phone from a barbershop. “The songs that were hot weren’t hot anymore, you know, people got their own families and shit. So niggas sat me down and was like, ‘Yo, we just kind of want to focus on you. You’re the best one.’”

He started to release music under the name Guapdad 4000, a name he conceived while brainstorming AIM handles with Kehlani, and performed for free at local art shows. “I’d be hanging my [paintings] and performing later on at night,” he said, “that’d be for like 15, 30 people at the most.” He battled depression and survived a suicide attempt in 2014. For years, he indulged in scamming – a volatile business, even when it works. “The money goes so fast, especially when designer is so expensive,” he said. “Maybe you can’t get some shit off. Maybe you buy a bad batch of [credit] cards. I was just doing bad. So I said I don’t want to scam no more, I just want to rap about it.”

Paul Middleton / Guapdad 4000

A slew of scamming Ls, including one disastrous scam that lost him $40,000 worth of Bitcoin, emboldened Guapdad to take rapping more seriously. Broke, he left Oakland for Los Angeles’ greener pastures. Due to his extensive history of scamming, he had a dismal credit score that prevented him from locking down an apartment, so he lived in the studio while he recorded his first mixtape, Scamboy Color. “My whole point of living there was trying to prove to myself that I didn’t want to do illegal shit. I wanted to come correct,” he explained.

Guapdad’s scamming spirit lives on in his music, and in particular in his music videos. In the video for “Scamboy,” he stars as Falcon Lopez, the pastor of First Fraudvangelical Black Baptist Church, in a fake commercial. In his “First Things First” video, he unexpectedly shows up at G-Eazy’s house in the middle of the night with extras and a full film crew ready to shoot. His various alter-egos – like Shia LaBustDown, the Ferragamo Falcon, the Valentino Viper, the Gucci Goat, the Armani Army Admiral, and Prada Pootie Tang – form an alliterative, kaleidoscopic smokescreen that colors his social media pages and seeps into his lyrics. “I’m like Jesus, God and the Holy Spirit,” he explained. “Like, they are three different names that embody the same celestial entity. But I’m starting to attribute some of the different names to different feelings, different time periods in the past.”

Sometimes it seems like Guapdad lives to troll; the day after Dior Deposits dropped, he ate a sucker punch from Russ backstage at a San Antonio music after he clowned Russ on the album. Other times, his creative restlessness reads as ambition. He says he has four TV pilots and four decks that he’s prepared to pitch “to anyone who wants to hear.” He co-designed the Dior Deposits cover art, and he still finds time to draw every day on his iPad. “Mostly all my art is self-portraits. I only paint myself,” he said. Hanging above his bed in the Scam Estate is a nearly life-size, gold-framed, high school senior portrait-style photo of him. Like his spiritual godfather Lil B, Guapdad possesses a radical combination of self-worship and self-deprecation that ultimately manifests as a borderline reckless self-belief.

You can learn a lot about Guapdad 4000 from his LinkedIn page, which he hasn’t updated in at least five years. His listed occupation is “Creative Genius” and his one “interest” is Boston Consulting Group. His bio reads as follows: “Rapper and Producer. Targeting mainstreams listers [sic] with abstract ideas and products. Let’s create something NEW.”

Words by Danny Schwartz