[AdmiralAsshat]

> My first encounter with "sideloading" I think was loading up a MP3 player with music, for some reason that was called "sideloading" by some people. In that case, "sideloading" was just transferring basically, nothing about installing.

Probably influenced by the original iPod, which really wanted you to sync your iPod with your iTunes library (conveniently directing you to purchase all of your music from Apple's platform). "Sideloading" referred to the few extra steps to get your computer to simply expose the iPod as a removable storage device and drag-and-drop your mp3s over that way.

It wouldn't have made sense in the context of other mp3 players, because for many of the ones I remember (like my Creative Zen Touch), that was the only way to add the mp3s. I don't think Creative even supplied a front-end media manager...or if they did, I never bothered installing it.

[raw_anon_1111]

Well actually..

Steve Jobs himself said in his famous “Thoughts on Music” letter that was posted on the Apple home page that less than 10% of users music on iPods were bought from iTunes.

> Probably influenced by the original iPod, which really wanted you to sync your iPod with your iTunes library (conveniently directing you to purchase all of your music from Apple's platform).

iTunes (the software) came out before the iTunes (the music store) and iPods and Apple actually marketed the iMacs as “rip mix burn”.

[ryandrake]

Even before the iTunes store appeared, I always hated the over-complicated import/sync pattern.

1. "Import" your files into iTunes "library"

2. "Sync" that library with a device

My computer already has a filesystem. Why do I need to involve some application's "library"? I hate applications that insist on grafting its own "library" container on top of my already-working filesystem. My OS already allows me to copy files. Why do I need to rely on that application to copy files? Just expose the thing as a mass storage device and let me use my OS!

[raw_anon_1111]

Because with iTunes, I could and did have regular playlists and smart playlists using conditions like ratings, last played, play count, number of times skipped (so that it would automatically be removed from a playlist if I continued to skip a song on my iPod or computer), genre, year released, etc.

You couldn’t have that metadata with just file syncing. Later when iTunes was introduced, it had to support DRM.

Later it also had podcast syncing.

I used iTunes to burn CDs before I had an iPod.

And don’t forget that Jobs being able to negotiate users being able to buy music on iTunes with DRM [1] and letting users burn them to a DRM free CD was so revolutionary that even Bill Gates was impressed.

https://9to5mac.com/2021/07/09/unearthed-email-shows-bill-ga...

[1] later Jobs argued in the same “Thoughts on Music” letter that instead of Apple licensing its DRM the record label should license DRM free music to everyone since most music was already sold as DRM free CDs and then everyone’s music could work anywhere. Only one record label took them up on the offer from day one. It wasn’t until 2009 that all of the record labels agreed.

[embedding-shape]

Yeah, people in my circles and also people on the internet would refer to it as "sideloading" even though none of us were using iPods (I think this was all before the iPod actually, but my memory is a bit hazy), just copy-paste the files with explorer.exe over to the built-in MP3 player storage, people calling it "sideloading".