His father’s passing, though, also spurred Cudi’s creativity. After catching him singing under his bed one day, Elsie pushed him to join the school choir. She bought Calvin and Hobbes anthologies to encourage his drawing. And when he took a serious interest in rap, she supported that, too. Still, the quiet melancholy never disappeared. After being “a C and D student with a teacher mom,” Cudi enrolled in Toledo University, only to drop out after a year studying film.

But he was also recording demos, funded by shifts at a local Applebee’s. While we’re talking, Cudi excitedly rummages through a stack of scratched-up CD-Rs, pulling one out that says KID MESC: RAP HARD with three different Ohio phone numbers written in black marker. This is his first demo, from 2001. He slides it into his MacBook, begging not to be judged. “I’m nervous, man!” There’s shoddy, chipmunk soul-style production and a rickety, East Coast–influenced flow, but it’s Cudi all over.

“I been drunk before, but I’m feeling this shit / I’ve been high before, but I’m feeling this shit,” he raps on “Party All the Time.” When the song is over, Cudi realizes it’s not so bad. “Man, I might redo this and release it!”

— Kid Cudi: How He Made It In America by SPIN