Last November, Steven P. Jobs finally achieved his long-sought goal of bringing the Beatles to iTunes. But years before he made the deal, he began working on the promotional campaign for the music, personally designing advertisements that would sit in virtual mothballs for as long as necessary.

“He just sat them there waiting for the day,” said Roger Faxon, the CEO of the EMI Group, the Beatles’ label. “They were beautiful ads.”

As the man who introduced the iPod, iPhone and iPad to the world, Jobs became a kind of folk hero of US business for his intuitive understanding of consumer sentiment and his ability to make deals with some of the most obstinate players in entertainment and media.

He was, according to Bono of U2, “one of a very small group of anarchic Americans who through technology literally invented the 21st century. We all miss the hardware software Elvis.”

In many ways, the Beatles agreement was the perfect distillation of Jobs’ determination — and his complete confidence — in melding technology and culture. But for the media companies at the other end of those deals, Jobs was a far more complex figure. As executives in music, film and publishing have learned, a deal with Jobs and Apple meant inclusion in one of the most important digital marketplaces on the planet, and the potential for greater sales than from any other outlet. But the deals were inevitably made on Jobs’ strict terms.

“Steve’s approach to the magazine industry was, ‘My way or the highway,”’ said Jann Wenner, the founder and editor of Rolling Stone, who dealt with Apple over the magazine’s iPad edition.

Of all media businesses, music has had the most fraught relationship with Apple. It was the first entertainment industry to find its basic business model shaken by the Internet, when Napster in 1999 ushered in mass illegal file sharing. ITunes was clearly the only workable solution, said one senior executive at a major label, but Jobs’ demands that songs be sold individually and all at 99 cents made the labels uncomfortable.

“He was a genius and he was creative, but he was also fairly imperious,” said Bill Werde, the editorial director of Billboard. “When Apple has leverage, Apple uses leverage.”

Stories about Jobs’ efforts to persuade the leaders of the industry to his side are legion. For years, he remained stubbornly, victoriously inflexible about matters like pricing. He personally demonstrated iTunes to figures like Bono and Jimmy Iovine, the chairman of Interscope Geffen A&M, wowing them in much the same way he did crowds of software developers and journalists at the company’s regular product introductions.

“We swallowed hard,” said the senior label executive, who did not want his name used because of Apple’s well-known secrecy about negotiations and contracts. “But if anybody could pull this off, Steve could.”

The iTunes store has sold 16 billion songs in its eight years in business. Yet for music companies, it has been a mixed blessing. Overall music sales declined 32 per cent in 2010 from 2003, when the iTunes store was introduced, according to the International Federation of the Phonographic Industry. Digital music, while still growing, has not made up for the money lost from CDs.

For many in other forms of media, however, Apple has all but saved the music labels from a far worse fate. For others, music has been an example of an industry that gave up too much control to Apple. The company faced a revolt from magazine and newspaper publishers this year when it insisted on keeping 30 per cent of the money from subscriptions sold in its app ecosystem and on controlling all customer data for those transactions. With services like Google offering more favourable terms to publishers, Apple agreed to some flexibility.

Hollywood’s relationship with Jobs has also been tense. As the founder of Pixar Animation Studios and the largest shareholder in the Walt Disney Company, Jobs was not cowed by Hollywood. Pixar, which Jobs subsidised for years before the company hit pay dirt with “Toy Story,” established the template for much of Hollywood’s output of well-crafted digital animation that combines fairy-tale narratives with sophisticated adult humor. (It also made Jobs one of Hollywood’s richest moguls and the single largest shareholder in Disney.)

But the major movie studios and television companies have dealt carefully with Apple. Jobs’ business genius, as many see it, has been his ability to negotiate and bring virtually any company into the Apple fold, while compromising little, if at all. His tenacity was the stuff of legend. But many executives say his love for art and media in even its most minute details made him persuasive.

Richard Stengel, the managing editor of Time, said despite Jobs’ reputation as a digital Svengali, he had an almost romantic attachment to print. “He used to talk about the aesthetics of magazine making,” Stengel said. “He always fancied himself as better than anybody else at anything. And I think one of his fantasy jobs would have been as a magazine editor.”

Jobs’ understanding of the mind of the consumer never failed to impress other executives, like Robert A. Iger, Disney’s CEO.

“He would call me on Saturday afternoons and we’d chat for an hour,” Iger said. “We had great talks about the future of digital media, and each one was about how people would ultimately consume things.”

“It was never about the distribution mechanism,” he said. “It was, ‘What will people want?’”