iTunes

Long-term owners

Just about everything I watch or listen to is served from the same iTunes Library I've had for over 20 years.

Jun 2026 · comment

I'm in the same boat as you, even with a botched migration about 12-14 years ago and am really passionate about this stance.

Nov 2025 · comment

What hackers pick instead

• WinampPeople recommend Winamp for its fast, simple, customizable interface, and old versions still run on Windows 11; the main caveat is that it feels dated.60recommend
• foobar2000People recommend it for its simple, customizable layout, broad format support, and long-running reliability, and it has no real equivalent. Critics say it is Windows-first and weaker on other platforms.54recommend
• PlexampMusic player valued for discovery in large libraries and smooth Plex server use. Main caveat: it costs money, and critics call the price too high.31recommend
• Audacious music playerPeople recommend it as a fast, minimal, cross-platform music player that plays almost any format and supports classic Winamp skins. The one recurring complaint is that it struggles with HiRes displays.17recommend
• SymfoniumPeople recommend it as a top Android music player for self-hosted libraries, and say it works well with Jellyfin and Navidrome.11recommend

Every quote

The 40 most detailed of 147 comments. Each links to the original.

1. When it just did what it was supposed to (rip CDs and put the contents, neatly labeled and organized on your iPod) it was unsurpassed to this day.

   Mixed · Jan 2026 · in “Tech Is Fun Again: The Tech Monoculture Is Finally Breaking”

2. iTunes had become this gigantic everything-but-the-kitchen-sink kind of monstrosity and I think it was the right call to split it up

   Mixed · Jun 2026 · in “Stop the Apple Music app from launching”

3. iTunes (Apple Music, not to be confused with Apple Music the service) is still here, still working with original hardware

   Recommends · Feb 2026 · in “Resizing windows on macOS Tahoe – the saga continues”

4. Just about everything I watch or listen to is served from the same iTunes Library I've had for over 20 years.

   Recommends · Jun 2026 · in “Stop the Apple Music app from launching”

5. Because with iTunes, I could and did have regular playlists and smart playlists using conditions like ratings

   Recommends · Nov 2025 · in “Android/Linux Dual Boot”

6. has worsening UX over time and it will prompt you to buy Apple Music's subscription service

   Mixed · Jan 2026 · in “Ask HN: How to go back to listening to MP3s?”

7. being able to plug in a cable and hit the big Sync button was really simple and convenient

   Mixed · Aug 2026 · in “Apple introduces M6 and M5 Ultra”

8. My plex library has my entire library that I've been curating since iTunes was released

   Mixed · Oct 2026 · in “Plex vulnerabilities being exploited in the wild to drop a cryptominer”

9. iTunes was also unrivaled in its first versions, before it became an everything app.

   Recommends · Aug 2026 · in “Apple introduces M6 and M5 Ultra”

10. This is not the Apple which lovingly created the first few versions of iTunes.

    Recommends · Jan 2026 · in “How Spotify Made Me Self Host”

11. Because back in the dawn of OS X it was legitimately a good music utility

    Recommends · Aug 2026 · in “Apple introduces M6 and M5 Ultra”

12. iTunes is still the best I have, mainly because it syncs well with iPhone

    Mixed · May 2026 · in “Show HN: We missed Winamp, so we built an audio player for macOS”

13. the level of seamless integration between iPhone and Windows via iTunes

    Recommends · Jan 2026 · in “Microsoft kills official way to activate Windows 11/10 without internet”

14. there was a time when iTunes actually had a clean, intuitive UI

    Mixed · Nov 2025 · in “Winamp clone in Swift for macOS”

15. It was a bloated mess, but somehow better than the horror-show

    Mixed · Jun 2026 · in “macOS 27 Wishlist: What Do You Want from Apple at WWDC 2026?”

16. probably objectively the best desktop music app ever created

    Recommends · Apr 2026 · in “Tim Cook to become Apple Executive Chairman”

17. you needed a computer with iTunes for the first use of iPad

    Mixed · Jan 2026 · in “Prediction: Microsoft Is Going to Do the Funniest Thing Imaginable”

18. Beautiful. I remember running iTunes 5 on my Powerbook G4

    Recommends · Nov 2025 · in “Winamp clone in Swift for macOS”

19. They've kept the local iTunes method working from day 1.

    Recommends · Mar 2026 · in “Setting up phones is a nightmare”

20. iTunes on Windows was horrible and it was even more horrible when trying to use it for managing Apple devices. Obscure errors, convoluted error mesages, slow...

    Criticizes · May 2026 · in “Show HN: We missed Winamp, so we built an audio player for macOS”

21. If you think the iPod software experience in the early 2000s was good then you and I had very different experiences with iTunes

    Criticizes · Jan 2026 · in “Tech Is Fun Again: The Tech Monoculture Is Finally Breaking”

22. Getting music on an ipod was always a pain unless you bought the music on itunes or ripped a music CD directly with itunes

    Criticizes · Mar 2026 · in “Apple Just Lost Me”

23. iTunes at the time was notorious for deleting all of your library if it thought you didn't buy something through them

    Criticizes · Jul 2026 · in “The lost joy of music piracy”

24. iTunes would take all your hard work, shake it around, rename all the files and dump them in a single folder

    Criticizes · Aug 2026 · in “Apple introduces M6 and M5 Ultra”

25. Then iTunes went all streaming and wiped out my local library, not the media files, just the library.

    Criticizes · May 2026 · in “Spotify Will Start Reserving Concert Tickets for Fans”

26. I've felt they are increasingly de-prioritizing the old iTunes business to focus on Apple TV+

    Criticizes · Jun 2026 · in “Fox to Buy Roku Streaming Service in $22B Deal”

27. Some of the most effective mechanisms in history for shifting people away from copyright infringement have been iTunes and Netflix.

    Recommends · Jun 2026 · in “European ISPs Want Rightsholders Held Accountable for Overblocking Damage”

28. I'm in the same boat as you, even with a botched migration about 12-14 years ago and am really passionate about this stance.

    Recommends · Nov 2025

29. iTunes integration was compelling enough that Palm implemented iPod imitation in the Pre so it would work with iTunes.

    Recommends · Jul 2026 · in “Nokia's 14 Years of Mobile-Phone Supremacy Ended in an Afternoon”

30. I'm the guy who fixed the wine bug that blocked new iTunes versions, because I like to keep my music in iTunes

    Recommends · Mar 2026 · in “MacBook Neo Is a 'Shock' to the PC Industry: Asus Co-CEO”

31. nothing has been more satisfying than an old unsupported version of iTunes that doesn’t even support FLAC

    Recommends · Dec 2025 · in “Ask HN: What Are You Working On? (December 2025)”

32. Apple had iTunes already, they very well could've acqui-hired and improved their service themselves.

    Mixed · Mar 2026 · in “AirPods Max 2”

33. I do agree that it had been getting worse and worse on Mac before it was rebranded "Music" in 2019.

    Mixed · May 2026 · in “Show HN: We missed Winamp, so we built an audio player for macOS”

34. Itunes will let me make playlists where if I own the song, I can't play it cause it's not synced.

    Mixed · May 2026 · in “Show HN: We missed Winamp, so we built an audio player for macOS”

35. if I don't buy the movie on Apple iTunes then it's almost always the case that I buy the blu-ray

    Mixed · Jun 2026 · in “If You Can't Hold It, You Don't Own It”

36. Apple managed to land on a good thing with Apple iTunes and iPhotos in the early oughts

    Recommends · Apr 2026 · in “Tim Cook to become Apple Executive Chairman”

37. the only way to get a custom ringtone was to buy one on iTunes at a hefty premium

    Mixed · Sep 2026 · in “Nokia Design Archive (2025)”

38. iTunes and Quicktime were never half as scummy as their modern counterparts are.

    Recommends · Sep 2026 · in “Apple has added persistent 'ads' to iOS, and it's driving users crazy”

39. if Apple blocks solutions from the App Store then they want you to use iTunes

    Mixed · Dec 2025 · in “Ask HN: Seeking advice in how to deal with frustration against big corps as dev”

40. the problem is that iTunes imposes a very “flat” structure on your library

    Mixed · May 2026 · in “Show HN: We missed Winamp, so we built an audio player for macOS”