Walter Isaacson’s authorised biography Steve Jobs (Little, Brown, Rs 799) contains a wealth of anecdotes. Here are some juicy ones...
![]() |
While in school, Jobs had set off an explosive under a teacher’s chair and pulled various other pranks, including dangling a giant illustration of the middle finger salute from the balcony with Swab Job written under it.
He was an incredibly fussy eater who stuck to extreme diets for most of his life. As a young man, he would fast for up to a week and make pronouncements like “I’m a fruitarian and only eat leaves picked by virgins in the moonlight”.
According to a friend, there is some truth to the story that he had turned orange after eating carrots for days.
Jobs believed, despite all evidences to the contrary, that his “pure” diet made it unnecessary for him to use deodorant even though he showered only once a week. While he was working at gaming company Atari, his in-charge had complained about his body odour. As a young man, Jobs walked around barefoot. When he was stressed, he would soak his feet in the toilet bowl!
Jobs was a great fan of Bob Dylan and The Beatles and had a huge collection of their bootlegs. The only time Jobs could recall being tongue-tied was in the presence of Bob Dylan in 2004. Jobs had wanted Dylan to perform at his 30th birthday party. He refused. Ella Fitzgerald provided the evening’s entertainment.
Jobs was in a relationship with singer Joan Baez for three years. He was 27, she was 41 when they met through her sister. One of Jobs’s friends said that he was attracted to her partly because she used to be Dylan’s lover.
In 1984, Jobs took the original Macintosh to Mick Jagger’s house at artist Andy Warhol’s insistence. The rockstar was not sure who Jobs was. The Apple boss later told his team: “I think he was on drugs. Either that or he’s brain-damaged.”
Jobs’s commencement speech at Stanford University in 2006 is well known. He had delivered talks at the university a number of times earlier. Once in 1982, he had asked students: “How many of you are virgins? How many of you have taken LSD?” He would later ask the same questions to an engineer he was interviewing for the position of software manager at Apple.
Jobs’s Mercedes did not have a licence plate. At Apple, he almost always parked in the space reserved for the disabled, next to the front door, sometimes in such a way that his vehicle blocked the slots of two cars. Employees made signs saying “Park Different”.
Burrell Smith, a key engineer at Apple, wanted to quit but was certain that Jobs would talk him into withdrawing his resignation. He told colleagues that he would walk into Jobs’s office, pull down his pants and pee on his desk so that he was fired. When Smith finally made an appointment and walked into the office, he found Jobs smiling broadly. “Are you gonna do it? Are you really gonna do it?” the boss asked. Smith was eventually allowed to leave less dramatically.
Bill Clinton had asked Jobs for advice on how to handle the Monica Lewinsky scandal. The Apple boss told the president that if he was involved, he should tell the country. During that time, a painting of a dress on a hanger went missing from Jobs’s house before the Clintons were to move in for a few days. The US secret service told Jobs’s wife that they had decided to hide it, “given the issue of the blue dress in the Lewinsky matter”.
Jobs had offered to create ads for Barack Obama’s 2008 campaign to become president but became annoyed when Obama’s strategist wasn’t totally deferential. Later, Jobs was unhappy that Obama had not called him after becoming president. In October 2010, when Obama was visiting the Silicon Valley, his aides had scheduled a session with Jobs. The Apple boss refused to meet him, saying that the president should have called personally and asked. Jobs’s wife eventually had to ask their son to come home from Stanford and persuade his father to meet Obama. When they met, Jobs told Obama at the outset: “You’re headed for a one-term presidency.”
Issey Miyake designed “like a hundred” signature black turtlenecks for Jobs so that he could wear them for the rest of his life.
While he was admitted to hospital for a liver transplant in 2009 and was barely conscious, he ripped off a mask that a pulmonologist tried to put over his face because he didn’t like its design. He wanted five different options for the mask, so that he could pick the design he liked best. He also wanted the oxygen monitor redesigned.
What was on Jobs’s iPod:
All six volumes of Bob Dylan’s bootleg series, 15 other Dylan albums, and songs from seven albums of The Beatles, six of the Rolling Stones and four of Joan Baez. Apart from that there was 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, The Monkees and Sam the Sham. Current musicians were represented by 10,000 Maniacs, Alicia Keys, Black Eyed Peas, Coldplay, Dido, Green Day, John Mayer, Moby, U2, Seal and Talking Heads. There were also recordings of Bach and three albums of Yo-Yo Ma, who he had asked to play at his funeral (he reportedly did). Jobs later moved his entire music collection to his iPad.
What was on Jobs’s iPad:
Three movies — Chinatown, The Bourne Ultimatum and Toy Story 3. One book — The Autobiography of a Yogi by Paramahansa Yogananda, which he had first read as a teenager, reread in India and read once a year since. He added Gregorian chants, Grateful Dead and Joni Mitchell to his music collection.