The Archie Jukebox 6000 was freaking huge because it used a laptop sized HDD. It was portable much like a boom box was portable, but at the size of a CD player and a small stack of CD’s it wasn’t clearly better.

The 2001 iPod cost 400$, but it was smaller than a CD player (4.02inx2.43inx0.78in) and could hold 1,000 songs. That’s point where it could start to kill off personal CD players.

Exactly, the Archie Jukebox didn't fit into a jeans pocket. There were MP3 players that did fit into a jeans pocket, but they used flash, which at the time only had the capacity for a few CDs at most. So, it was the iPod with which you could carry your entire music library (or a good chunk of it, nearly 100 CDs) in your pocket.

Wikipedia also claims (https://en.wikipedia.org/wiki/Archos_Jukebox_series):

“The Jukebox is historically notable for shipping with a user interface and operating system so unfriendly and bug-ridden as to inspire Björn Stenberg and other programmers to develop a superior, free and open-source replacement operating system. This project became Rockbox.[citation needed]”

Anybody know whether that (especially the “so unfriendly and bug-ridden” part; that Rockbox started on that device seems less controversial to me) is true?

Yes, but nobody ever heard of it until it was mentioned as an also-ran in Wikipedia's article about DAPs. (That said, I did just finish updating my prior comment to reflect that the iPod wasn't the first HDD-based player to market, but I think it is still fair to say it was the first one that mattered.)

Kids had MP3 players before the iPod. I remember them in high school and yes they were a known music player alternative to CDs. The iPod landed with a unified marketing campaign that promoted itself as a music device vs an MP3 player. The marketing campaign was sleek and different.

But those flash based MP3 players didn't have much storage (certainly not several GB), and typically had a terrible UI, if they could handle meta data (song, artist, album, genre) at all.

Before the iPod, a DAP was an alternative to a Discman. After, it was the other way around - at first for rich kids whose families could afford the requisite Macs for iTunes, but once iTunes for Windows came out, a Discman was what you had if you were poor.

Even if they weren't nearly as ubiquitous as they would become, people absolutely had heard of DAPs before the iPod came out. And, like the iPhone, it took 2 or 3 generations before it was obvious to a lot of people that this was something different--in part because of the ecosystem.

Here for example, is a not very flattering account of the introduction from PC Magazine: https://web.archive.org/web/20011121170057/http:/www.interac...