Mac Miller has died. TMZ reports that the Pittsburgh rapper was found earlier today at his home in the San Fernando Valley, dead of an apparent overdose, and Billboard has confirmed the news. Miller has battled substance abuse for some time, and he was arrested for a DUI and a hit-and-run in May. He was 26.

Miller was born Malcolm James McCormick in Pittsburgh. In high school, he started rapping, and he also taught himself to play several instruments. In 2007, a 15-year-old Miller, under the name EZ Mac, released his first mixtape But My Mackin’ Ain’t Easy. In 2010, he signed with the large indie Rostrum and released the breakout mixtape K.I.D.S.. In 2011, he released Blue Slide Park, his proper debut album, and it was the first independently distributed album in 16 years to debut at the #1 spot on the Billboard album charts.

Miller’s early music, though popular, was fratty and immature. But as he kept working, he developed as both a rapper and a producer. His second album, 2013’s Watching Movies With The Sound Off, was a huge leap, and Miller managed to hang alongside well-curated guests like Jay Electronica, Earl Sweatshirt, and Schoolboy Q. Under his Larry Fisherman alias, he produced all of Vince Staples’ 2013 mixtape Stolen Youth.

For the next few years, Miller walked a strange line. He was a hugely popular figure in a lot of senses. He was the subject of an MTV reality show, and he dated Ariana Grande for a while. But he was also a sonic explorer, always looking for ways to make his own music richer and headier. His records aren’t all great, but they all have moments of greatness, moments where Miller challenged both himself and his audience.

Miller has spoken of his addiction to promethazine, and he’s rapped about a lot of other drugs, as well. When he and Grande broke up earlier this year, she characterized the relationship as “toxic” on Twitter. Last month, Miller released Swimming — his last album, and probably his best. On that album, Miller collaborated with musicians like Jon Brion, Thundercat, and Flying Lotus, creating a spaced-out funk sound and delving into his own problems, failures, and hopes. He sounded like he was trying his best to get better.

Below, watch some of Miller’s videos.