Kim Kardashian, girlfriend (2012 to present)
Selita Ebanks (linked in 2010)
Amber Rose, ex-girlfriend (2009 to 2010; on & off)
Alexis Phifer, ex-girlfriend (2002 to 2008; on & off, engaged)
Brooke Crittenden, ex-girlfriend (2005 to 2006)
1996 College Dropout
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.)
Jay-Z's Architect
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.
Near Death Experience
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."
Slow Jamz, Fast Start
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."
Sore Loser
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."
It's His Party
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.
Cover Artist
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.
Sophomore Success
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."
Hurricane of Controversy
"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 televisedConcert 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."
Diamond Life
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."
Ugly American
Even after being named Best Hip-Hop Artist at the MTV Europe Music Awards in Copenhagen, a fuming Weststorms on stage as the award for Best Video is being given to Parisian duo Justice vs. Simian. In a profanity-laced tirade, West says he should have won the prize for "Touch the Sky," because his video "cost a million dollars, Pamela Anderson was in it."
50 Cent Challenges Kanye
Rapper 50 Cent, who is releasing his Curtis album on the same day (Sept. 11) as West's Graduation album, challenges West. 50 Cent, 31, tells hip-hop Web site SOHH.com, "Let's raise the stakes. If Kanye West sells more records than 50 Cent on September 11...I won't put out anymore solo albums." Weeks later, West, 29, tells XXL magazine, "My biggest inspiration and biggest competition is Justin Timberlake...We push each other." Although the two rappers make peace, West widely outsells 50 Cent in first week sales, according to Nielsen SoundScan: 957,000 copies to 691,000 copies.
Kanye West's Mother Dies
West's mother, Donda West, dies of heart disease after undergoing plastic surgery. Donda, 58, a retired professor and former chairwoman of the Chicago State University English department, was a tireless supporter of her son as he both earned success and stirred up controversy. "He came out of the womb looking like he had that attitude," Donda, who released her memoirRaising Kanye: Life Lessons from the Mother of aHip-Hop Superstar, told InStyle earlier this year.
Kanye Pays Tribute to Mother
West delivers an emotional tribute to his late mother at the 2008 Grammy Awards, performing "Hey Mama," a song from his second album. He also goes home with his third Best Rap Album Grammy for Graduation. During his acceptance speech, West says, "I know you wouldn't want me to stop and you want me to be the No. 1 artist in the world, and Mama, all I'm going to do is keep making you proud. We run this!"
Turning Sorrow into Success
West's fourth album, 808s & Heartbreak, tops the Billboard charts with 450,000 copies sold. The experimental disc in which West sings rather than raps using audio processors, receives mixed reviews. "What makes 808s & Heartbreak worthy of adulation and applause is that it's made by an artist who carries with him no other agenda but to make him and those who listen to him feel something," raves Vibe. The album is largely inspired by the death of West's mother and his break-up with fiancée Alexis Phifer.
New Year, New Love
During New York Fashion Week, West steps out with new squeeze, model Amber Rose. The couple makes a fashionable pair, wearing attention-grabbing ensembles around the world. "He'll pick out something and he'll be like 'Babe, just ... no.,'" she tells Elle. "I'm more electric pink and bright yellow. And Kanye's more like nude and bone."
Stealing the Show
During Taylor Swift's acceptance speech for best female video at the MTV VMAs, West jumps onstageand announces that "Beyoncé had one of the best videos of all time." After celebs like Kelly Clarkson and even President Obama criticize his antics, West apologizes in a phone call to Swift.
Creating a 'Fantasy'
West's latest album My Beautiful Dark Twisted Fantasytops the Billboard 200 album charts in its first week and is heralded as a work of genius by critics. Rolling Stonesays it's "his most maniacally inspired music yet…Nobody halfway sane could have made this album," while Spin praises it as "a blessing."
Kanye's Coveted 'Throne'
West joins forces with Jay-Z for their collaborative album Watch the Throne, which debuts at No. 1 on Billboard's 200 albums chart on the strength of their hit single "Otis." "They're hip-hop monarchs, andWatch the Throne, doesn't shrink from its own hype,"Rolling Stone says of the record, which helps West lead the 2011 Grammys race with seven nominations. He takes home four awards, including best rap album for 2010's My Beautiful Dark Twisted Fantasy and best rap performance for "Otis" with Jay-Z.
Back to Reality
In his new song "Theraflu," West sings about his feelings for Kim Kardashian, with whom he isreportedly dating. "I admit I fell in love with Kim ... 'Round the same time she fell in love with him," the rapper says, referring to Kardashian's soon-to-be ex Kris Humphries. "Kanye and I have been friends for years...You never know what the future holds,"Kardashian coyly says of their relationship on the Todayshow.
Baby On the Way
The rapper surprises concert goers at his Atlantic City show when he reveals Kardashian is pregnant. "It's true!! Kanye and I are expecting a baby," she confirms in a blog post. "We feel so blessed and lucky and wish that in addition to both of our families, his mom and my dad could be here to celebrate this special time with us."
It's a Girl!
Kardashian confirms she and West are expecting a daughter on the eighth season premiere of Keeping Upwith the Kardashians. "I'm so excited we're having a girl … I know that's really what Kanye has always wanted," she says on the show, which airs the same day as herbaby shower. "Kim and Kanye were so cute – he rubbed her belly," Kardashian's aunt Karen Houghton told PEOPLE. "They're just really blessed. It's such a happy day."
Special Delivery
West's girlfriend Kim Kardashian gives birth a few weeks before her expected July due date to their first child – a daughter. "She's doing great and she's beautiful! So very exciting," Kardashian's mom Kris Jenner tells HLN.