R.I.P. Apple’s iTunes: Remembering the Best, Worst and Wackiest Moments

The iTunes brand is no more. Nearly two decades after introducing the world to the digital store-library hybrid, Apple announced at its annual global developers conference on Monday that it will shutter the iTunes software this fall, replacing it with three standalone programs for music, television and podcasts. While core features will largely remain intact — the ability to buy songs, for example, remains and is merely moving to the new “Music” app — the death of the iTunes brand marks the closing of a particular epoch in industry history. Below are some of the most iconic moments of the digital-download era that iTunes ushered in.

2003: A revolution begins with giddy, colorful fanfare

Steve Jobs didn’t just bring the world an online music store in the early 2000s — he gave fans a sustainable and user-friendly way to pay for albums rather than pirating them off the internet. To promote the store, he roped in big names like Bob Dylan to help make the project a success. The iTunes Music Store served as a jukebox, discovery center and record shop (one free of judging clerks side-eyeing you from behind the counter) all in one. Time praised iTunes in 2003 as the “coolest invention” of the year, and the software — alongside its cheerful hardware counterpart, the iPod — would go on to reinvigorate the slipping music industry in the lawless internet age, even though profits could never compare to the gold mine of the record-store era.

In its first week alone, iTunes sold 1 million downloads and displaced Walmart and Best Buy as the top music retailer. Apple’s pretty and ubiquitous “silhouette” advertisements helped solidify the new line of products in fans’ minds.

2004: Green Day try to save music with iTunes and Pepsi

Not every promo worked out. At the 2004 Super Bowl, Apple partnered with Pepsi for an anti-piracy advertisement featuring a Green Day cover of “I Fought the Law” that was expensive, well-publicized and now infamous for its total failure. The ad featured teens who had apparently been prosecuted for illegal downloading — and who helped announce that Apple and Pepsi would be giving away 100 million iTunes songs for free. What made the ill-received ad worse was that the Pepsi bottles containing the song redemption codes were not as widely distributed as they were supposed to be, leading to only 5 million of the 100 million songs being claimed. “We had hoped the redemptions would have been higher,” Katie Cotton, Apple’s vice president of communications at the time, admitted.

2010: iTunes Ping is an unloved nightmare

While iTunes users have long complained of bloated software, the case of iTunes Ping, Apple’s short-lived social network, was one where they were heard and heeded. Apple launched Ping in 2010 to help iTunes users share their favorite artists and music with one another — but it spawned more ridicule than adoration. “The customer voted and said, ‘This isn’t something that I want to put a lot of energy into,’” Apple CEO Tim Cook acknowledged in 2012.

2011: The Beatles finally come on board

In 2011, Apple and iTunes scored their biggest win to date: The Beatles’ catalog. After withholding all their records for years, the band agreed to distribute their music through the iTunes Store with a direct royalty stream to their record company and publisher — a deal that industry sources said was one of the most lucrative in music history. The Beatles’ embracing of iTunes came around the same time as that of other holdouts like Led Zeppelin, Kid Rock, Metallica and AC/DC, and it signaled to music fans that iTunes’ business model was here to stay. (At least until the next iteration, a.k.a. Spotify’s streaming platform, came along.)

2014: U2 forces its album on the world

One day in 2014, half a billion music fans woke up and found a U2 album inexplicably in their library. Via “compulsory free download,” Apple had delivered the Irish rock band’s new record Songs of Innocence to every iTunes subscriber at the time — a move that seemed advantageous to both parties, as U2 had been a champion of the iTunes Music Store from the start. “We wanted to reach as many people as possible,” U2 manager Guy Oseary told Rolling Stone. Jimmy Iovine explained the thinking behind the gimmick: “There’s not much rock in the zeitgeist, so what the band were trying to do is defy gravity. And whatever tools you can use to do that, you should use.”

But iTunes users were less than happy. Some, like the writers of Wired, condemned the giveaway as “worse than spam,” and for a brief while, U2 seemed like the most hated band in America. (Within a week, Apple released instructions to iTunes users to explain how to delete the album, opening with the passive-aggressive line: “If you would like U2’s Songs of Innocence removed from your iTunes music library and iTunes purchases, you can choose to have it removed.”)

One Month Later: Bono apologizes for forcing U2’s album on the world

“Oops,” Bono himself said, less than a month later in a Facebook Q&A, in reply to a question about the mandatory download. “I’m sorry about that. I had this beautiful idea and we got carried away with ourselves. Artists are prone to that kind of thing: [a] drop of megalomania, touch of generosity, dash of self-promotion and deep fear that these songs that we poured our life into over the last few years mightn’t be heard. There’s a lot of noise out there. I guess we got a little noisy ourselves to get through it.”


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