An English major at Chicago State University, where his mother, Donda, chairs the department, West quits school to pursue his music career full-time. "He said, 'Mom, I can do this, and I don't need to go to college, because I've had a professor in the house with me my whole life,'" Donda West tells Time. "I'm thinking, this boy is at it again. He always could twirl a word." (West's parents divorced when he was young.)
After turning out hit singles for Common, Ludacris and Cam'Ron, among others, West gets his big break when Jay-Z asks him to produce several tracks on his chart-topping album The Blueprint.
On his way home from a marathon recording session in L.A., West crashes his Lexus after falling asleep at the wheel. While recovering in the hospital, West pens "Through the Wire," a song about the crash where he jokes about drinking "a Boost for breakfast, a Ensure for dizzert/Somebody ordered pancakes, I just sip the sizzurp." He'll record the song three weeks later with his jaw still wired shut. The finished track convinces Roc-A-Fella Records to let him move in front of the mic and push through approval for his first solo album. "Death," West tells Time, "is the best thing that can ever happen to a rapper. Almost dying isn't bad either."
West's debut album The College Dropout is an immediate hit, selling 441,000 copies in its first week. Not that West needs sales figures to validate his work. "You can't judge The College Dropout. It's something completely different," he tells the AP. "It's definitely a classic, if I [could] step aside from myself and say that."
Nominated for three American Music Awards, West walks out of the show after losing the Best New Artist award to country newcomer Gretchen Wilson. "I feel I was definitely robbed...I was the best new artist this year," he complains backstage to the Associated Press. "I don't know if I'll be back at this award show next year." A month later he was a little more circumspect. "I came up to Gretchen [before the Grammy press conference] and apologized," he tells Entertainment Weekly. "And I want to apologize to my black role models, like Jay-Z and Oprah Winfrey, for being overemotional. I was doing a disservice to everything my forefathers have done to allow black people to get to this place."
The most nominated artist at the 47th Annual Grammy Awards with 10 nods, West takes home three trophies – Best Rap Album, Best Rap Song for "Jesus Walks" and Best R&B Song for producing Alicia Keys' "You Don't Know My Name." Rocking in an Yves Saint Laurent suit, West celebrates by throwing his own party along with Boost Mobile in L.A.'s Miracle Mile district. It gets so packed that the fire marshal closes the guest list at 1 a.m. West wins three more awards at the following year's ceremony, including Best Rap Album for Late Registration.
With the headline "Hip-Hop's Class Act," West becomes one of the rare entertainers to appear on the cover of Time. The lengthy article details the contradictions of The College Dropout and of West himself, who admits that when starting out in hip-hop, "It was a strike against me that I didn't wear baggy jeans and jerseys and that I never hustled, never sold drugs." In April, Time had tapped West as one of the year's 100 most influential people.
West shoots to No. 1 with his second album, Late Registration, topping the Billboard album and singles charts thanks to "Gold Digger," his collaboration with Jamie Foxx. "It uses profanity, and it's shocking and controversial and f----- up and funny," West tells Playboy about the song. "It's so perfect and out of the park."
"George Bush doesn't care about black people." Those seven words become a national headline when West strays from his scripted monologue at the live televised Concert for Hurricane Relief. He criticizes the government's response in helping Katrina victims. With a shocked looking Mike Myers at his side, West's comments air live on NBC on the East Coast but are edited out of the West Coast version later that night. "People have lost their lives, lost their families," he says a week later on The Ellen DeGeneres Show. "It's the least I could do to go up there and say something from my heart."
West proposes to Alexis Phifer on the island of Capri. West split with model Brooke Crittenden earlier this year and has dated Phifer off and on for years. In 2008, they call off their engagement. "It's always sad when things like this end, and we remain friends," Phifer tells PEOPLE. "I wish him the best in his future and all of his endeavors. He's one of the most talented people I've ever met."
BIOGRAPHY (top to bottom): Sara Jaye/ABACA; Rich Schultz/AP; Simon Frederick/Getty; Lester Cohen/WireImage; Reed Saxon/AP; Kwaku Alston; Matt Peyton/NBC; FAME