A year or so after 2010’s Thank Me Later hit, Drake was browsing art in LA when a neon sign caught his eye: “LESS DRAKE, MORE TUPAC.” At first, he felt like ripping it off the wall. Instead, he bought it. After all, he figured if someone puts your name next to Tupac, you must be doing something right. Born Aubrey Drake Graham in Toronto in 1986, he—like Tupac—became the voice of a generation and prism for his pop-cultural moment, starting with 2011’s sumptuous Take Care, a career-defining magnum opus that’s included in Apple Music’s 100 Best Albums list. Was he an R&B singer who rapped or a rapper who sang? Was he really that sad, or just exploiting a cultural preference for male vulnerability? From the jump, he let his contradictions define him: tender but cruel, sober one minute and drunk-dialing the next, a guy who could convince you he was an underdog from his perch on top of the world. Yet as lurid as his inner world is, the proof lies in his reach outward. A Drake project can incorporate house and club music (2017’s More Life, 2022’s Honestly, Nevermind) and red-eyed trap (2022’s 21 Savage collab Her Loss) with equal conviction and at no loss to the subjectivity at the center. “I obviously spend a lot of time in my own world,” he told Apple Music in 2016. “But when I do take a look at the broader scope of things, I’ve always tried to make music that transcends gender, nationality—to try and unify people. Because that’s really what it’s about.” Even after cementing his prowess many times over, Drake still retains the capacity to surprise. His 2023 poetry collection Titles Ruin Everything with repeat collaborator Kenza Samir proved intentionally fragmented, while his very public 2024 beef with Kendrick Lamar became a focal point not just in hip-hop fandom, but also global mainstream culture. At this point, he’s such an indelible part of the firmament that his slightest move can trigger aftershocks far beyond his immediate reach.