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The Sound Track of His Life

Jimmy Iovine, Bono, Jobs, and The Edge, 2004

On His iPod

As the iPod phenomenon grew, it spawned a question that was asked of presidential candidates, B-list celebrities, first dates, the queen of England, and just about anyone else with white earbuds: “What’s on your iPod?” The parlor game took off when Elisabeth Bumiller wrote a piece in the New York Times in early 2005 dissecting the answer that President George W. Bush gave when she asked him that question. “Bush’s iPod is heavy on traditional country singers,” she reported. “He has selections by Van Morrison, whose ‘Brown Eyed Girl’ is a Bush favorite, and by John Fogerty, most predictably ‘Centerfield.’” She got a Rolling Stone editor, Joe Levy, to analyze the selection, and he commented, “One thing that’s interesting is that the president likes artists who don’t like him.”

“Simply handing over your iPod to a friend, your blind date, or the total stranger sitting next to you on the plane opens you up like a book,” Steven Levy wrote in The Perfect Thing. “All somebody needs to do is scroll through your library on that click wheel, and, musically speaking, you’re naked. It’s not just what you like—it’s who you are.” So one day, when we were sitting in his living room listening to music, I asked Jobs to let me see his. As we sat there, he flicked through his favorite songs.

Not surprisingly, there were all six volumes of Dylan’s bootleg series, including the tracks Jobs had first started worshipping when he and Wozniak were able to score them on reel-to-reel tapes years before the series was officially released. In addition, there were fifteen other Dylan albums, starting with his first, Bob Dylan (1962), but going only up to Oh Mercy (1989). Jobs had spent a lot of time arguing with Andy Hertzfeld and others that Dylan’s subsequent albums, indeed any of his albums after Blood on the Tracks (1975), were not as powerful as his early performances. The one exception he made was Dylan’s track “Things Have Changed” from the 2000 movie Wonder Boys. Notably his iPod did not include Empire Burlesque (1985), the album that Hertzfeld had brought him the weekend he was ousted from Apple.

The other great trove on his iPod was the Beatles. He included songs from seven of their albums: A Hard Day’s Night, Abbey Road, Help!, Let It Be, Magical Mystery Tour, Meet the Beatles! and Sgt. Pepper’s Lonely Hearts Club Band. The solo albums missed the cut. The Rolling Stones clocked in next, with six albums: Emotional Rescue, Flashpoint, Jump Back, Some Girls, Sticky Fingers, and Tattoo You. In the case of the Dylan and the Beatles albums, most were included in their entirety. But true to his belief that albums can and should be disaggregated, those of the Stones and most other artists on his iPod included only three or four cuts. His onetime girlfriend Joan Baez was amply represented by selections from four albums, including two different versions of “Love Is Just a Four-Letter Word.”

His iPod selections were those of a kid from the seventies with his heart in the sixties. There were Aretha, B. B. King, Buddy Holly, Buffalo Springfield, Don McLean, Donovan, the Doors, Janis Joplin, Jefferson Airplane, Jimi Hendrix, Johnny Cash, John Mellencamp, Simon and Garfunkel, and even The Monkees (“I’m a Believer”) and Sam the Sham (“Wooly Bully”). Only about a quarter of the songs were from more contemporary artists, such as 10,000 Maniacs, Alicia Keys, Black Eyed Peas, Coldplay, Dido, Green Day, John Mayer (a friend of both his and Apple), Moby (likewise), U2, Seal, and Talking Heads. As for classical music, there were a few recordings of Bach, including the Brandenburg Concertos, and three albums by Yo-Yo Ma.

Jobs told Sheryl Crow in May 2003 that he was downloading some Eminem tracks, admitting, “He’s starting to grow on me.” James Vincent subsequently took him to an Eminem concert. Even so, the rapper missed making it onto Jobs’s iPod. As Jobs said to Vincent after the concert, “I don’t know . . .” He later told me, “I respect Eminem as an artist, but I just don’t want to listen to his music, and I can’t relate to his values the way I can to Dylan’s.”

His favorites did not change over the years. When the iPad 2 came out in March 2011, he transferred his favorite music to it. One afternoon we sat in his living room as he scrolled through the songs on his new iPad and, with a mellow nostalgia, tapped on ones he wanted to hear.

We went through the usual Dylan and Beatles favorites, then he became more reflective and tapped on a Gregorian chant, “Spiritus Domini,” performed by Benedictine monks. For a minute or so he zoned out, almost in a trance. “That’s really beautiful,” he murmured. He followed with Bach’s Second Brandenburg Concerto and a fugue from The Well-Tempered Clavier. Bach, he declared, was his favorite classical composer. He was particularly fond of listening to the contrasts between the two versions of the “Goldberg Variations” that Glenn Gould recorded, the first in 1955 as a twenty-two-year-old little-known pianist and the second in 1981, a year before he died. “They’re like night and day,” Jobs said after playing them sequentially one afternoon. “The first is an exuberant, young, brilliant piece, played so fast it’s a revelation. The later one is so much more spare and stark. You sense a very deep soul who’s been through a lot in life. It’s deeper and wiser.” Jobs was on his third medical leave that afternoon when he played both versions, and I asked which he liked better. “Gould liked the later version much better,” he said. “I used to like the earlier, exuberant one. But now I can see where he was coming from.”

He then jumped from the sublime to the sixties: Donovan’s “Catch the Wind.” When he noticed me look askance, he protested, “Donovan did some really good stuff, really.” He punched up “Mellow Yellow,” and then admitted that perhaps it was not the best example. “It sounded better when we were young.”

I asked what music from our childhood actually held up well these days. He scrolled down the list on his iPad and called up the Grateful Dead’s 1969 song “Uncle John’s Band.” He nodded along with the lyrics: “When life looks like Easy Street, there is danger at your door.” For a moment we were back at that tumultuous time when the mellowness of the sixties was ending in discord. “Whoa, oh, what I want to know is, are you kind?”

Then he turned to Joni Mitchell. “She had a kid she put up for adoption,” he said. “This song is about her little girl.” He tapped on “Little Green,” and we listened to the mournful melody and lyrics that describe the feelings of a mother who gives up a child. “So you sign all the papers in the family name / You’re sad and you’re sorry, but you’re not ashamed.” I asked whether he still often thought about being put up for adoption. “No, not much,” he said. “Not too often.”

These days, he said, he thought more about getting older than about his birth. That led him to play Joni Mitchell’s greatest song, “Both Sides Now,” with its lyrics about being older and wiser: “I’ve looked at life from both sides now, / From win and lose, and still somehow, / It’s life’s illusions I recall, / I really don’t know life at all.” As Glenn Gould had done with Bach’s “Goldberg Variations,” Mitchell had recorded “Both Sides Now” many years apart, first in 1969 and then in an excruciatingly haunting slow version in 2000. He played the latter. “It’s interesting how people age,” he noted.

Some people, he added, don’t age well even when they are young. I asked who he had in mind. “John Mayer is one of the best guitar players who’s ever lived, and I’m just afraid he’s blowing it big time,” Jobs replied. Jobs liked Mayer and occasionally had him over for dinner in Palo Alto. When he was twenty-seven, Mayer appeared at the January 2004 Macworld, where Jobs introduced GarageBand, and he became a fixture at the event most years. Jobs punched up Mayer’s hit “Gravity.” The lyrics are about a guy filled with love who inexplicably dreams of ways to throw it away: “Gravity is working against me, / And gravity wants to bring me down.” Jobs shook his head and commented, “I think he’s a really good kid underneath, but he’s just been out of control.”

At the end of the listening session, I asked him a well-worn question: the Beatles or the Stones? “If the vault was on fire and I could grab only one set of master tapes, I would grab the Beatles,” he answered. “The hard one would be between the Beatles and Dylan. Somebody else could have replicated the Stones. No one could have been Dylan or the Beatles.” As he was ruminating about how fortunate we were to have all of them when we were growing up, his son, then eighteen, came in the room. “Reed doesn’t understand,” Jobs lamented. Or perhaps he did. He was wearing a Joan Baez T-shirt, with the words “Forever Young” on it.

Bob Dylan

The only time Jobs can ever recall being tongue-tied was in the presence of Bob Dylan. He was playing near Palo Alto in October 2004, and Jobs was recovering from his first cancer surgery. Dylan was not a gregarious man, not a Bono or a Bowie. He was never Jobs’s friend, nor did he care to be. He did, however, invite Jobs to visit him at his hotel before the concert. Jobs recalled:

We sat on the patio outside his room and talked for two hours. I was really nervous, because he was one of my heroes. And I was also afraid that he wouldn’t be really smart anymore, that he’d be a caricature of himself, like happens to a lot of people. But I was delighted. He was as sharp as a tack. He was everything I’d hoped. He was really open and honest. He was just telling me about his life and about writing his songs. He said, “They just came through me, it wasn’t like I was having to compose them. That doesn’t happen anymore, I just can’t write them that way anymore.” Then he paused and said to me with his raspy voice and little smile, “But I still can sing them.”

The next time Dylan played nearby, he invited Jobs to drop by his tricked-up tour bus just before the concert. When Dylan asked what his favorite song was, Jobs said “One Too Many Mornings.” So Dylan sang it that night. After the concert, as Jobs was walking out the back, the tour bus came by and screeched to a stop. The door flipped open. “So, did you hear my song I sang for you?” Dylan rasped. Then he drove off. When Jobs tells the tale, he does a pretty good impression of Dylan’s voice. “He’s one of my all-time heroes,” Jobs recalled. “My love for him has grown over the years, it’s ripened. I can’t figure out how he did it when he was so young.”

A few months after seeing him in concert, Jobs came up with a grandiose plan. The iTunes Store should offer a digital “boxed set” of every Dylan song every recorded, more than seven hundred in all, for $199. Jobs would be the curator of Dylan for the digital age. But Andy Lack of Sony, which was Dylan’s label, was in no mood to make a deal without some serious concessions regarding iTunes. In addition, Lack felt the price was too low and would cheapen Dylan. “Bob is a national treasure,” said Lack, “and Steve wanted him on iTunes at a price that commoditized him.” It got to the heart of the problems that Lack and other record executives were having with Jobs: He was getting to set the price points, not them. So Lack said no.

“Okay, then I will call Dylan directly,” Jobs said. But it was not the type of thing that Dylan ever dealt with, so it fell to his agent, Jeff Rosen, to sort things out.

“It’s a really bad idea,” Lack told Rosen, showing him the numbers. “Bob is Steve’s hero. He’ll sweeten the deal.” Lack had both a professional and a personal desire to fend Jobs off, even to yank his chain a bit. So he made an offer to Rosen. “I will write you a check for a million dollars tomorrow if you hold off for the time being.” As Lack later explained, it was an advance against future royalties, “one of those accounting things record companies do.” Rosen called back forty-five minutes later and accepted. “Andy worked things out with us and asked us not to do it, which we didn’t,” he recalled. “I think Andy gave us some sort of an advance to hold off doing it.”

By 2006, however, Lack had stepped aside as the CEO of what was by then Sony BMG, and Jobs reopened negotiations. He sent Dylan an iPod with all of his songs on it, and he showed Rosen the type of marketing campaign that Apple could mount. In August he announced a grand deal. It allowed Apple to sell the $199 digital boxed set of all the songs Dylan ever recorded, plus the exclusive right to offer Dylan’s new album, Modern Times, for pre-release orders. “Bob Dylan is one of the most respected poets and musicians of our time, and he is a personal hero of mine,” Jobs said at the announcement. The 773-track set included forty-two rarities, such as a 1961 tape of “Wade in the Water” made in a Minnesota hotel, a 1962 version of “Handsome Molly” from a live concert at the Gaslight Café in Greenwich Village, the truly awesome rendition of “Mr. Tambourine Man” from the 1964 Newport Folk Festival (Jobs’s favorite), and an acoustic version of “Outlaw Blues” from 1965.

As part of the deal, Dylan appeared in a television ad for the iPod, featuring his new album, Modern Times. This was one of the most astonishing cases of flipping the script since Tom Sawyer persuaded his friends to whitewash the fence. In the past, getting celebrities to do an ad required paying them a lot of money. But by 2006 the tables were turned. Major artists wanted to appear in iPod ads; the exposure would guarantee success. James Vincent had predicted this a few years earlier, when Jobs said he had contacts with many musicians and could pay them to appear in ads. “No, things are going to soon change,” Vincent replied. “Apple is a different kind of brand, and it’s cooler than the brand of most artists. We should talk about the opportunity we offer the bands, not pay them.”

Lee Clow recalled that there was actually some resistance among the younger staffers at Apple and the ad agency to using Dylan. “They wondered whether he was still cool enough,” Clow said. Jobs would hear none of that. He was thrilled to have Dylan.

Jobs became obsessed by every detail of the Dylan commercial. Rosen flew to Cupertino so that they could go through the album and pick the song they wanted to use, which ended up being “Someday Baby.” Jobs approved a test video that Clow made using a stand-in for Dylan, which was then shot in Nashville with Dylan himself. But when it came back, Jobs hated it. It wasn’t distinctive enough. He wanted a new style. So Clow hired another director, and Rosen was able to convince Dylan to retape the entire commercial. This time it was done with a gently backlit cowboy-hatted Dylan sitting on a stool, strumming and singing, while a hip woman in a newsboy cap dances with her iPod. Jobs loved it.

The ad showed the halo effect of the iPod’s marketing: It helped Dylan win a younger audience, just as the iPod had done for Apple computers. Because of the ad, Dylan’s album was number one on the Billboard chart its first week, topping hot-selling albums by Christina Aguilera and ............
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