Wtf. I am looking into this. I'll post what I find. (editing...... done)
http://www.youtube.com/watch?v=nSBbF5IkxnA
>"For everyone who does not know this is jesse rutherford on the neighbourhood before the band he had many different projects such as jesse rozz or jesse james it all the same person (jesse rutherford) this is his song." - yoChristian98
http://mp3class.com/mp3-Jesse+Rozz+Too+Cold%28demo%29.html (uploaded in 2007, nothing there)
Found it here (same as youtube vid): http://ex.fm/search/Jesse%20Rozz
Can't find anything about a chilean kid though.
> "Go to datpiff and search Jesse James truth hurts truth heals and you'll find the real Jesse. This kid is fake as fuck and stole his music and put a diff name." - youtube comments again.
So the song sweater weather has been around for years.. in some form or another.
Using HTML5 audio to play your streams is pretty straightforward. You can get easily find streams to online radio stations via sites like Shout cast.com. For streaming individual tracks I'd look at the ex.fm API.
The main difficulty will creating the interface and handling the APIs while switching between streams. Here's a pretty good tutorial on putting it all together
I found a link to what I think is the original. Short tune unfortunately
http://ex.fm/song/8pg8z/girlworld-CBoyardee
It also seems to be much faster than the one used in the italo disco video
I've got a NAS box with all of my music on it. I connect to it on my PCs via simple sharing and on my TVs with a DLNA server on the box.
I've also got an iPod with a bit of music on it, but I hardly ever use it since the native player can't play FLAC and 80%+ of my library is FLAC.
I use ex.fm if I can't access my box.