Karen Valby
January 27, 2014 AT 12:00 PM EST

When Kanye West called in December to talk about being one of ENTERTAINMENT WEEKLY’s Entertainers of the Year, something seemed off. West just wasn’t as interested in going on and on about how great he is. Admittedly, he had earned his bragging rights. His Grammy-winning debut, 2004’s The College Dropout, sold 3 million copies and boasted innovative marvels like “Through the Wire” and “Jesus Walks.” And just when his preening pose started to bore, didn’t he make a good case for himself with his follow-up, Late Registration? Even more breathless critical acclaim followed, along with double-platinum sales, another slew of Grammy nominations, and a string of daring provocations, like when he denounced President Bush during a live Hurricane Katrina telethon. Here, on the phone, was another chance to gloat. And sure, he couldn’t help comparing himself to the Michaels (Jordan and Jackson), but his heart didn’t seem in it. What West really wanted to talk about was his next move.

“Do you think my new video should be ‘Touch the Sky’ or ‘We Major?'” the 28-year-old hip-hop wunderkind wondered earnestly. Go with the first one, we replied. But he wanted enthusiasm! “The way you answered,” he said, “it sounded like there was a question mark at the end.” West’s prenup anthem, “Gold Digger,” had enjoyed a great run, living atop the pop charts for 10 weeks with its neon video spinning constantly on MTV. But a follow-up single, the graceful uplifter “Heard ‘Em Say,” stalled at No. 26, and the album started to lose some of its chart luster. The video, directed by the usually inspired Michel Gondry, was a cheesy dud, and West knew it. So he demanded a second version, an arty black-and-white clip, but it too failed to catch on. The unexpected misses had left him shaken. “So you think that ‘Touch the Sky’ could provide the energy to give the album a sales resurgence like ‘Hollaback Girl’ did for Gwen Stefani?” he asked anxiously. “I know I have to come up with some out-of-the-ballpark ideas for the video. I can’t miss on this one!”

Cut to a blustery day in January on an Indian reservation overlooking the Grand Canyon. According to West, the “Touch the Sky” video will cost more than $1 million, with almost three-quarters of the budget coming out of his own pocket. He’s determined to make it the spectacle to top all spectacles. The video boasts an Evel Knievel ’70s story line sending up West’s overarching hubris; a rocket ship, motorcycles, a hilarious reference to his Bush comments, Nia Long, and Pamela Anderson. He wanted to hire a bear to charge him in one shot, but logistical woes — and common sense, perhaps — got in his way.

It’s day three of the grueling four-day shoot, and in West’s trailer — a decidedly untricked-out den with a crummy bathroom and yogurt and juice in the fridge — “Touch the Sky” track producer Just Blaze gets a haircut from West’s personal groomer, Ibn. “Kanye’s still like an eager little kid in a candy store,” says Just Blaze, who’s known him for almost a decade. “The world might see someone who’s very arrogant and cocky and talks all this craziness, but at the end of the day the music he’s making lives up to it. And he’s smart enough to know that if he ever puts out a bad record, people will pounce. Kanye’s put himself on such a high pedestal that he knows he has to stay on top.” Outside in the wind and cold, an aerial camera crane swoops around West, who stands near the edge of a very high cliff.

Working late into the evening out on that precipice, West missed the helicopter that was supposed to fly him back to Las Vegas, where he’s staying during the shoot. So he bounces happily instead into a shabby crew van, and picks up where he left off in December. “What did you think of the ‘Heard ‘Em Say’ videos?” he asks, spooning strawberry yogurt. Tell him that Michel Gondry’s original version, in which the rapper and a couple of cutie-pie kids frolic in Macy’s, was an oversentimental disappointment and he nods his head. “For real? You thought it was bad? Yeah, that’s what I thought too.”

And so begins a three-hour ride, from the bumpiest desert road into the most aggressively garish of American cities. Along the way, West hits all the high and low notes of hope and despair, his relentless ambition and his equally powerful fear of failure.

WEST The thing is, it’s not like I didn’t try hard as hell on the “Heard ‘Em Say” videos. I’ve got a bunch of “Damn, we should have tried this” regrets. I’m banking on having good taste, and I was off about what I thought would work in the marketplace. It’s the one thing in 2005 that I feel like I really failed at.

EW So in the end, Kanye West is his own worst critic?

WEST In the end, in the middle, and in the beginning. You don’t know how bad it hurts to fail like that. So it means so much to me for this next video to be great. Instead of this being the last hurrah, this video could put me back at the awards shows.

EW Speaking of awards shows, are you excited about your eight Grammy nominations?

WEST If God gave me the choice between winning Grammys or having a really awesome across-the-board “Heard ‘Em Say” video, I would choose an awesome video. I want you to want to run home to see a Kanye West video.

EW So you no longer care about winning awards?

WEST Well, when I was making the album I would use the Grammys as one of my muses. The media makes it seem like I feel I should always win even if I’m not in the category. But, duh, I feel like I should win Album of the Year because, um, it was. [Laughs] People always ask, “What’s the key to success?” And someone will say, “Well, I don’t know, but I know the key to failure is trying to please everybody.”

EW That sounds like sane advice.

WEST I disagree with that, though. I am scared of failure. I was scared to work on the second album, but I have eight people in the studio while I’m working on a track and I ask them a million questions. “What did you think of this? Do you think this is it?” And I want the truth. You can’t learn anything from a compliment. So I take all their opinions and by the time the record’s out, you can’t tell me s— about it.

EW I have friends who admire your music, but they hate your attitude. Does it bother you that people might think you’re an ass?

WEST There are times where I have leeway to spaz out because I’m a successful artist, but I really am trying my best not to be a jerk. I’m definitely a better person than I was two years ago. It’s hard coming in — that struggle to get through the gate and everybody’s dissing you, A&R people saying, “You’re never going to make it! No one’s ever going to play this track!” People talk to you the way guards talk to prisoners. So for me to finally make it, I felt like I was fresh out of jail. And you know I got to go back to the people who used to bring me down. I’m Robert De Niro in Heat! I got to go back for one more time.

EW But why can’t you let it go if only 95 percent of a review is glowing? On your “Touch the Sky” tour, you took time each night to lambast all of the reviewers who dared to criticize you.

WEST I’m trying to take the power out of their words and give it back to me. And I thought it would be entertaining. It always gets an “ahh” out of the audience.

[pagebreak]EW Have you ever looked out at your audience and felt dismayed by the number of white faces in the crowd?

WEST Never! You can never shun either audience. I love Fiona Apple and Portishead and those are two of the joints I wanted to base Late Registration on. But when my first single, “Diamonds From Sierra Leone” [which samples Shirley Bassey’s “Diamonds Are Forever”], came out, the lukewarm response I got from the hood put me in my place. It’s like they were saying, “Kanye, we still need you to bring us good quality black music. Don’t stray.” I’m not saying the hood can’t handle heavy instrumentation, but Curtis Mayfield and Ray Charles connect to black people. Black people never listened to Shirley Bassey when they were shorties. Every time I do a video, every time I do a song, I have to keep in mind everybody. It’s Mission: Impossible for real. I’m the only artist who has a responsibility to hit five, six different types of fans every time.

From the back of the van, someone suggests that OutKast faces similar obligations. West thinks on this for a second before relenting. “Yo, that was a great response,” he admits. His bodyguard, Barry, interrupts to point out the van’s slow coil down around the Hoover Dam, lit up at night to look like diamonds tossed down a massive well. “Yo, imagine if you shot a video out there!” says Barry. West peers out the window, eyes wide like a little boy on a cross-country family trip, and starts hopping up and down in his seat. “Man, this is a nice car ride, huh? You get inspiration from a car ride like this! Hmm…” He pauses, looking around. “I guarantee you that this dam was put together way better than those levees in New Orleans.”

EW You have a history of speaking out, against President Bush, against the black community for what you say is a tradition of homophobia. Do you think you’ll ever come out against all the “bitches” and the “ho’s” in rap lyrics?

WEST I’m not sure that’s really my movement. I think in the daily life of a black male, we gay-bash way more than we disrespect women. We would call a gay guy a fag to his face. But if we walked up to a woman and said “Aiight, bitch!” we would know that was disrespectful. I remember five years ago I was in this clothing store in Greenwich Village with my old girlfriend. I said the word fag kind of loud and there were some gay dudes in the store. My girlfriend was like, “Yo, c’mon, step into the new millennium.” Well, my level of consciousness has since raised. And I actually think that standing up for gays was even more crazy than bad-mouthing the president. In the black community someone could label you gay and bring your career down. But that was me showing what black people are really about today, or at least what we need to be about.

EW Did the inevitable whisperings about your own sexuality make you regret ever saying anything?

WEST One of my friends said, “Yo, I used to wear a College Dropout T-shirt and think that it was cool. But after you said that, I just stopped wearing it.” When you stand up for any form of civil rights, you put yourself in the line of fire. But I feel like I’m here to change people’s hearts and minds, to say something that’s right for a change. And it goes all the way down the line, from telling people to stop being so cliché, to stop saying what you think your record label wants you to say, to stop giving drab acceptance speeches. Speaking from the heart is so much more entertaining.

EW Do you ever allow yourself to just be dull and quiet? Just zone out with a good book?

WEST No, I don’t. I feel like I’m too busy writing history to read it.

EW Groan.

WEST Ha! I’ve had everything from the past six years written down in my head. I’ll put together a collage of an album sequence in my head, or this “Touch the Sky” video; I’ll sequence out my whole next year and my outfit for tomorrow. I see music, too. Like a bass drum will be all round, in burgundies and browns; pianos—ladolodoludulololo! — are in the sky blue range; the kick drums — puh kickaakick-ka, ahpuhpuhkickakick! — that s— is dark, dark, dark espresso brown; and the snare is like an eggshell cream. I completely visualize the beat before I do it.

EW In the end, what do you think you’re best at?

WEST My greatest talent, more so than being a rapper, is the ability to produce, to grab things that seem like they don’t belong and put them together. I love building things, all the labor and refining and fine-tuning. My favorite thing in the world is postproduction. I like it more than sex.

EW [Laughs] Huh.

WEST And I like sex a lot! When I’m working, when I’m creating my gifts for the world, I want it to be good. I’m like the guy in The Aviator. They already made a movie about my life story.

EW But Howard Hughes ended up crazy and alone.

WEST Well, I hope I can avoid that part. At some point, I’m getting out of the rap biz. Maybe in three years, I’ll be a movie producer. I have a meeting on Monday with Steven Spielberg! Maybe I’ll act sometimes, in Spike Lee or Quentin Tarantino movies. But it would be such a shame for me to stop making music, because I’m just so good.

In the drive’s final stretch, with West’s third 18-hour day in a row drawing to a close, his bodyguard perks up. “I know where we are,” he announces happily. “There’s a Kentucky Fried Chicken right up the road! Get ready to pull over.”

Ask West what he’s got planned for the rest of his evening in Sin City, and he laughs. “Yo, Barry, y’all want to go to a strip club with me later tonight? Nah, I’m kidding. I’m going to just take a bath and call my girlfriend, who’s a regular girl, the funniest girl I ever met, with a regular job, by the way.”

West drifts off and starts singing one of the lines from “Touch the Sky” — “I’m trying to right my wrongs,” he repeats over and over under his breath — before suddenly breaking into a now-familiar lament. “‘Heard ‘Em Say’ is my favorite song of all time that I ever did! So why couldn’t I have had a good video for it?” he whines. “Man, I feel like I sent my gifted child to a bad school.”

The winking twinkle of the Las Vegas skyline in the distance distracts him from his obsessive hand-wringing. “On a beautiful road trip like this,” decides West, “you really have to appreciate all those hours in the studio. Look at all the s— I get to see and do! I was in the helicopter the other day coming back from the Grand Canyon with the sun setting in the background, and I just thought, Life is good. You have to appreciate how good things are, even with all the problems and the headaches. Maybe if Kurt Cobain had just rode in one helicopter in his lifetime, he’d still be here with us.”

Finally arriving back at the hotel at 10 p.m., somebody complains about having to turn around and wake up tomorrow at 3 a.m. to start the drive back to the video shoot. “Yo, y’all got room for me in the car?” says West, who’d earlier been told that as the star, he could sleep in until seven. “I wanted to get some rest, but I’d rather get up and go back to work.”

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