With his slick voice and playful persona, he makes his music look easy; but that's not the whole story.

Anderson .Paak slid under the industry’s collective radar for a long time. An R&B singer with a raw, unpolished voice and an old-school hip-hop sensibility, he was relegated to the underground for much of his career. Now, at age 30, he’s got a hit record, a spot in the XXL 2016 Freshman Class, and a catalogue of verses for legendary L.A. artists Dr. Dre and Schoolboy Q. He’s currently tearing up the festival circuit with his live band The Free Nationals, and he’ll continue to do so at Voodoo this Sunday.

I’ve seen .Paak perform three times over the past six months. At each show, he’s flirted shamelessly with the women in the audience, made “yo momma” jokes at the crowd’s expense, and even stopped his band mid-song and made them start over just to be an asshole. (I wasn’t positive it was a skit until I saw him do it the same way twice.) Nevertheless, the crowd eats it up every time. With his overabundance of talent and charisma, he’s able to pull off the douchebag act seamlessly.

From an unknown twentysomething to the next American rap star, .Paak seems to have a knack for sliding up ladders—the success ladder, the prestige ladder, the precarious social ladder of the L.A. music scene. As with most success stories, though, .Paak’s climb to stardom wasn’t as easy as all that. His playful persona and smooth-as-butter vocals belie a rough past of struggle and disappointment.

Brandon Paak Anderson graduated high school a de facto orphan--his mother convicted of fraud and headed to jail for seven years, his father already doing a 14-year stint for domestic violence. He floated around, working odd jobs to make ends meet, but found himself homeless in 2011 after being abruptly let go from his first steady work at a weed farm in Santa Barbara.

Even in light of his hardships, it would be easy to view his sudden rise to fame and fortune as a self-interested, ruthless street hustle, but that would be just as reductive. At 25, .Paak was not only a homeless ex-pot farmer, but also a new father, which made his situation even more dire. He found work at his old church in Oxnard, California, where he’d learned to play the drums, and eventually landed a more permanent gig drumming for American idol finalist Haley Reinhart. He’s slid behind a drum set every time I’ve seen him live, and it’s always the most exciting part of the show.

Needless to say, .Paak isn’t as irreverent as he appears on stage. In an interview with NPR, he explained his moniker’s unusual punctuation. “The dot stands for detail,” he said. “I feel that people only take you as serious as you take yourself. I spent a lot of time working on my craft, developing my style, and after I came out of my little incubation I promised that I would pay attention to detail.”

He got his big break when Dr. Dre brought him into the studio to work on his Grammy-nominated album Compton (2015). In January, he released Malibu, his second full-length project, and it has since stood up as one of the best albums of the year.

Last Friday, .Paak and the innovative Stones Throw producer Knxwledge (the duo go by NxWorries) released their studio debut Yes Lawd!. For .Paak, it’s not only an excellent project, but also a masterful nod to the underground, reassuring the day-one fans that despite his newfound fame, he doesn’t plan on selling out any time soon. Only .Paak knows which ladder he will choose to slide up next.