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.”