Since his debut, Kid Cudi has treated his career like a Jungle Gym. The Ohio-raised, New York-based rapper playfully explored the fusion of hip-hop and indie on his infectious breakthrough single “Day ’n’ Nite” and 2010’s drowsy, indelible “Pursuit of Happiness” with MGMT and Ratatat. His sudden fame saw him go toe to toe with his G.O.O.D. Music boss Kanye West (“Erase Me”), King Chip (“Just What I Am”), Pharrell Williams (“Surfin’”), and Travis Scott (“THE SCOTTS”) in the decade that followed, while also completing an ambitious trilogy with his psychedelic Man on the Moon albums. For Cudi, creation is ultimately about unlocking access to a higher power, and he turned trap beats into another means for transcendence on 2024’s harder-edged outing INSANO. Observe the haunted self-reflections of “TORTURED” and the low-slung swagger of the A$AP Rocky-assisted “WOW.” Maintaining a freewheeling sense of creativity across his many multimedia pursuits, he still feels like an outsider made good.