iTunes

Description

I remember the exact moment iTunes went from being software that I liked to being software that I was trapped in. It was 2008, I had just purchased my first iPod Nano — the third generation, the fat square one that everyone made fun of — and I plugged it into my family’s Windows XP desktop computer to load it with music. iTunes opened up automatically, scanned my hard drive, found my MP3 collection and promptly organized 4,000 songs into a structure of libraries I did not ask for.

Albums that I had carefully sorted out into folders by genre were rearranged alphabetically. Tracks that I had downloaded individually from various places were grouped under “Unknown Artist.” And one Metallica album somehow got split into three separate entries because the metadata on some tracks said “Metallica” and others said “metallica” with a lowercase M. I spent the rest of that evening manually repairing tags and learning about what ID3 metadata was. I was sixteen. I should have been outside.

iTunes started out in January 2001 as a Mac-only music player, a rebranding of a program called SoundJam MP that Apple acquired and gutted. The Windows version came in 2003 and that was the version that most of the world actually used because in 2003, most of the world used Windows. The iTunes Store was introduced the same year and it changed everything. A dollar per song. Legal downloads. Album art that appeared automatically.

For people who had been fighting it out on Kazaa and Limewire and risking both malware and lawsuits to get music, paying 99 cents to download a song that came with proper tags and artwork and did not turn out to be a mislabeled Bill Clinton speech, well, that was the future. And it was. The iTunes Store sold one million songs within its first five days. By 2010, it was the world’s largest music retailer (bigger than Walmart). Steve Jobs did not just create a music store. He persuaded an entire industry that had been fighting digital distribution to get on board and iTunes was the vehicle.

The problem is that Apple kept welding on new rooms to a house that was never designed to be this big.

First it was music. Then podcasts. Then audiobooks. Then movies and TV shows. Then apps for iPhone and iPad. Then iTunes U for educational material. Then Ping, Apple’s take on a music social network that nobody used and everyone forgot existed. Then Apple Music streaming. Then iCloud Music Library. Each addition made the application more heavy, slower, confusing and harder to navigate. By 2015, iTunes for Windows was a complete disaster.

Opening it took between fifteen and twenty seconds on a machine that could boot Windows itself in thirty. Syncing an iPhone meant waiting for iTunes to detect an iPhone, then waiting for it to back up that iPhone, then waiting for it to verify that it back up that iPhone, then finally letting you do what you actually wanted — unless it threw an ambiguous error code like “Error -54” or “Error 0xE8000015” and refused to explain what went wrong. I once spent forty minutes trying to sync a playlist to my iPhone 6 and wound up deconstructing the phone because iTunes said the sync session had “failed to start.” Twelve songs were on the playlist. Twelve.

The Windows version was always the neglected child. Apple designed iTunes for macOS first, and then ported it to Windows, with varying degrees of care, which over time approached zero. The application used Apple’s own UI framework, not native Windows controls, which meant that it never looked or felt like a Windows program. Scrolling was slightly off. Buttons did not react like buttons in Windows. The preferences menu was under “Edit” rather than “Tools” where a Windows user would expect it to be.

The installer included Bonjour, Apple Software Update, Apple Mobile Device Support and Apple Application Support – four different background services that ran at startup, used memory and sometimes clashed with other software. Uninstalling iTunes on Windows required uninstalling 6 different programs in the right order, and if you got it wrong, the uninstaller for one part would fail because another part was still running. I watched a YouTube tutorial in 2017 that was eleven minutes long and focused solely on the proper removal of iTunes from Windows. Eleven minutes to uninstall a music player.

And yet — and I cannot believe I am about to defend it — iTunes at its peak was genuinely good at being a music library. The Smart Playlists feature was genius. You could have rules: songs added in the last month, played less than three times, rated four stars or higher, genre is not holiday. iTunes would build the playlist automatically and update it as your library changed. I had a Smart Playlist named “Forgotten Favorites” – songs with a rating of four or five stars that I hadn’t played in over six months. It brought back tracks I loved, and simply stopped thinking about. No streaming algorithm has ever done this as well, because streaming algorithms optimize for engagement and Apple Music has no idea that I rated a song five stars on my iPod in 2009. That data died with iTunes.

The rating system was one of the quiet losses. Five stars. Simple. You listened to a song, you rated it, and over time your library was a curated reflection of your taste. I rated all of the songs I owned. Over 6000 tracks with a star rating that I personally assigned. When Apple Music came along and streaming was the new ownership, ratings were irrelevant. You do not rate songs that you do not own. You “heart” them, which is a binary choice — like or not like — that contains none of the nuance of deciding whether a song is a three or a four. The difference between a three-star song and a four-star song is everything. A three is fine. A four is the song you would put on a mixtape. Apple flattened that distinction into a heart icon and called it progress.

The iTunes Store still exists in 2026, technically, but it is a ghost town compared to what it was. Apple quit reporting individual download sales years ago, which tells you all you need to know. The store page is loaded inside Apple Music on Mac and the Apple TV app on Windows. The finding requires the knowledge that it exists. Buying a song — actually owning an MP3 that lives on your hard drive and can’t be taken away by a licensing disagreement — is a feeling of rebellion in an age where every company wants you to rent everything forever. I do buy albums from the iTunes Store from time to time, partly because I want to own them and partly because of a stubborn loyalty to a purchasing model that the entire industry has abandoned.

Apple stopped iTunes on the Mac in 2019 with the release of macOS Catalina. They divide it into three applications: Music, Podcasts and Apple TV. The Music app took over the library management features and Apple Music streaming. Podcasts got its own separate app. Movies and TV shows went to Apple TV. On paper, this was the right decision. iTunes was a bloated monster attempting to do seven things at once and doing none of them well. In practice, the Music app on Mac is fine — faster than late-era iTunes, cleaner interface, still has Smart Playlists buried in the menus if you know where to look.

But it lost some features during the split. Some visualizer options were lost. App management for iOS devices was removed years ago. The DJ feature — which used to allow you to crossfade between tracks with a simple interface — was gone. Each feature in itself was minor. Collectively, they added up to the feeling that Apple was gradually taking away all the things that made iTunes feel like yours, and substituting an interface optimized for a subscription service.

On Windows, iTunes had a longer life than it should have. Apple finally made the Apple Music app, the Apple TV app, and the Apple Devices app available for Windows in the Microsoft Store in 2023 and 2024. The classic iTunes desktop application still exists and still works if you download it from Apple’s website, but it is clearly in maintenance mode — receiving security patches and compatibility updates but no new features. Using iTunes on Windows in 2026 is like going to a restaurant, and it’s technically still open, but half the lights are out and the menu hasn’t been updated in three years. Everything functions. Nothing is new. The staff looks tired.

I want to be clear about one thing: for all its bloat, all its slowness, all its Windows sins, iTunes was the most important piece of consumer software in the history of digital music. It did not just play music. It developed the economic model that saved the recording industry from piracy. It provided a distribution platform for independent artists that did not require a record deal. It helped the podcast go from being a niche format to a mainstream medium. It made purchasing digital media normal. Every streaming service that exists today — Spotify, Apple Music, YouTube Music, Tidal, all of them — exists in an ecosystem that iTunes built. Spotify did not make people believe it was OK to pay for digital music. iTunes did that 10 years ago. Spotify just convinced them that renting was better than buying.

My iPod Nano is in a drawer somewhere. The last time I turned it on was two years ago and it worked then. The battery contained enough charge to play an hour or so of music. The screen was tiny. The click wheel was mechanical and satisfying in a way that touchscreens never will be. And every song on it had a star rating, a play count, and a last played date – a complete record of what I loved and when I loved it. That data exists nowhere else. iTunes put it there, and nothing that replaced iTunes thought it was worth keeping.

The software is dead. It earned its death. But I miss what it was before it forgot what it was supposed to be.