iTunes

November 6, 2003: After porting iTunes to Windows, Apple sets a new record for digital music sales: a massive 1.5 million downloads in one week.

Bringing the iTunes Music Store to PC users opens up a new, lucrative market for Apple. The record-breaking sales clock in at five times more than the 300,000 downloads that peer-to-peer file-sharing service Napster achieved in its debut week (remember it?). And 1.5 million is more than double the 600,000 iTunes downloads per week Apple reported selling to Mac users prior to the Windows release.

October 31, 2005: Less than three weeks after launching video downloads with iTunes 6, Apple reveals that it has already sold more than 1 million music videos.

Apple’s dive into the online digital video market — with 2,000 music videos, Pixar short films and a selection of hit TV shows for $1.99 — looks like the logical next step after selling individual songs on iTunes. Passing the 1 million download benchmark so quickly suggests the plan is a roaring success.

October 16, 2003: Six months after opening the iTunes Music Store for Mac owners, Apple expands the service to Windows computers. This gives PC owners a new, legitimate way to download — and pay for — songs at a time when digital piracy threatens the music industry.

Apple CEO Steve Jobs later quips that making iTunes available to Windows owners is akin to “giving a glass of ice water to somebody in hell.”

October 9, 1991: A court orders Apple to pay $26.5 million to Apple Corps, The Beatles’ record label and holding company, for trademark infringement. The end of this Beatles versus Apple lawsuit marks the second time Cupertino is forced to pay the English rock band.

The ruling comes a decade after Apple swore it would never get into the music business.

October 1, 2011: Just days before Apple plans to unveil the iPhone 4s, the device’s name leaks after the latest iTunes beta inadvertently spills the beans.

The code also reveals that Apple’s new handset will come in black and white color options.

September 15, 2014: Responding to its disastrous U2 album giveaway, Apple provides iPhone owners with a tool for wiping all signs of Songs of Innocence from their phones.

It comes after one of the strangest PR debacles in Apple history. After putting a free copy of U2’s latest release on every iPhone owner’s handset as a special promotion, millions find themselves with an album they didn’t order in their iTunes library. Many weren’t happy about it.

September 8, 2003: Apple reveals that the iTunes Music Store recently sold its 10 millionth song download. The tune in question? Avril Lavigne’s “Complicated.”

Come to think of it, “You fall and you crawl and you break and you take what you get and you turn it into [success]” describes Apple pretty well in the late ’90s and early 2000s.

May 24, 2013: Apple begins phasing out the option to download movie trailers from its once enormously popular iTunes Movie Trailers website.

The move signals a major change in the way people consume digital content as the internet evolves. Downloads will continue to decline, as streaming services like YouTube and Netflix pick up steam.

May 4, 2011: Reports circulate that Apple is negotiating with carriers to bring over-the-air updates to iOS, beginning with iOS 5.

Such a move would free iPhone owners from using iTunes to get updates for their devices. That means no more plugging an iPhone into a computer via USB to download the latest version of iOS.

April 28, 2003: Apple opens the iTunes Music Store, revolutionizing the music industry and digital distribution of content.

At a time when getting music online mostly means illegal downloads from pirate services like Napster, iTunes quickly proves that customers will pay for songs — provided the service is good enough.

March 21, 2007: Apple launches the Apple TV, a gleaming-white set-top box with a remote control, for bringing iTunes media to the living room.

Unfortunately, the device lacks key features needed to make it a killer entertainment system. It’s something of a missed opportunity for Apple.

March 15, 2004: The iTunes Music Store hits a musical milestone, having sold an astonishing 50 million songs in less than a year. The achievement cements Apple’s place at the center of the rapidly changing music business — at least for the moment.

“Crossing 50 million songs is a major milestone for iTunes and the emerging digital music era,” Apple CEO Steve Jobs says in a statement. “With over 50 million songs already downloaded and an additional 2.5 million songs being downloaded every week, it’s increasingly difficult to imagine others ever catching up with iTunes.”

February 26, 2008: Less than five years after launching, the iTunes Music Store becomes the No. 2 music retailer in the United States, second only to Walmart.

In that relatively short period, iTunes sells more than 4 billion songs to more than 50 million customers. The rapid rise to prominence stands as a massive achievement for Apple — and for the revolutionary digital distribution model Cupertino helped pioneer. If you’re looking for ways to use iTunes on MacBook, check out this milestone in Apple’s history.

November 20, 2007: In a milestone for iTunes movie distribution, Purple Violets becomes the first feature film to launch exclusively on Apple’s platform.

A romantic comedy directed by Edward Burns, Purple Violets stars Selma Blair, Debra Messing and Patrick Wilson. With limited offers from Hollywood’s traditional players, the filmmakers pin their hopes on iTunes distribution as an alternative way to get their movie in front of viewers.

Windows users can now download full versions of the Apple Music and Apple TV applications, as well as a new Apple Devices app. They make the venerable iTunes app almost obsolete.

The software combination is the new way to manage an iPhone or iPad on a Windows PC.

The iTunes Store application in the just-released iOS 17.2 simply redirects users to the Apple TV app for accessing previously purchased films and TV series.

The iTunes app for iPhone and iPad is now exclusively for music. For video, go directly to the Apple TV app.

Big-time PDF applications like Adobe Acrobat are great, but for many folks, splurging on them seems like hauling a pricey, seven-course banquet to a picnic at the beach. Many people are better off spending less to get only what they need. (You wouldn’t want to get sand in the caviar.)

Editor’s note: We originally published this illustrated history of the iPod to celebrate the device’s 10th anniversary on Oct. 22, 2011 (and updated it a decade later). We republished it on May 10, 2022, when Apple finally pulled the plug on the iPod.

The iPod grew out of Steve Jobs’ digital hub strategy. Life was going digital. People were plugging all kinds of devices into their computers: digital cameras, camcorders, MP3 players.

The computer was the central device, the “digital hub,” that could be used to edit photos and movies or manage a large music library. Jobs tasked Apple’s programmers with making software for editing photos, movies and managing digital music. While they were doing this, they discovered that all the early MP3 players were horrible. Jobs asked his top hardware guy, Jon Rubinstein, to see if Apple could do better.

An accidental collaboration with Apple saved NBC sitcom The Office from cancellation during its second season.

A fifth-generation iPod took a starring role in an episode of the comedy series. Then, the unlikely cameo spurred sales of reruns of the show on iTunes. And the rest is history.

Apple rolled out a new version of iTunes for Windows on Monday alongside iOS and iPadOS 15, but it should be avoided at all costs if your system isn’t set up in English. iTunes no longer works under any other language.

The problem seems to affect the version 12.12.0.6 version of iTunes no matter where it’s downloaded from — the Microsoft Store or directly from Apple — which means it’s not currently possible for some users to sync their devices.

So, you’ve already installed the iPadOS 15 beta beta on your iPad and now some of your favorite apps and features are broken. Don’t worry — it’s really easy (if a little time-consuming) to revert back to iPadOS 14.

We’ll show you how.

If you’ve already installed the iOS 15 beta on your iPhone and run into issues, you might want to downgrade to iOS 14 until more stable releases are available. Luckily, it’s really easy to do that if you have a Mac handy.

We’ll show you how.

A federal judge gave the go ahead to a lawsuit that claims Apple is tricking customers with the iTunes “Buy” button. There are questions about whether what’s happening qualifies as a purchase of the movie or TV show.

Apple was hoping to have the suite completely dismissed. As it is, the company may have to make a change to the way it offers this type of content.

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Over a platter of sushi, Steve Jobs once bragged to Amazon CEO Jeff Bezos that Apple had created the greatest Windows application ever built. The Apple co-founder then suggested, in a roundabout way, that the software could kill a major stream of revenue for Amazon.

Jobs was referring to iTunes for Windows, which Apple introduced in October 2003 (and which Jobs later referred to as the equivalent of “giving a glass of ice water to somebody in hell.”) Bezos got a look at iTunes for Windows before the rest of the world did. And he also endured a typically Jobsian dig about CDs and Amazon’s future.

January 9, 2001: Steve Jobs introduces customers to iTunes at Macworld.

In a world before the iPod or the iTunes Store, iTunes is simply described by Apple as, “the world’s best and easiest to use jukebox software that lets users create and manage their own music library on their Mac.” Even the biggest Apple fanboy can’t imagine just how significant a step this will be for Apple.