I can't tell you how many times I listened to the same songs on my Ipod during my trip. I basically stopped listening to my Ipod, because I had listened to them so many times. By the time I made it to SE Asia I had been traveling for about 7 months, and I needed a new play list. I had no idea how this was going to happen until I arrived in Vang Vien, Laos.
There was this internet cafe that was located across the street from the only Indian restaurant in town. This internet cafe would allow you to drop off your Ipod one day and pick up your Ipod the next day with new songs on it! They would charge you $1 US Dollar to upload 12 songs.
Since I hadn't had any new music for 7 months I decided to go crazy and spend $5 US dollars on new songs. The internet cafe had a huge catalog of music. They had a ton of US artists, and also some European artists to choose from in this catalog. All I had to do is fill out a card with what albums or songs that I wanted to upload and give the card to the owner of the cafe. The next day I picked it up and had new music. It was as simple as that!
I also saw another internet cafes that offered Ipod songs to upload in Phnom Phen, Cambodia. Other than that I didn't see too many other places around the world advertising in the window to upload new songs onto your Ipod. This is probably because it is illegal to do in other countries, but who is going to say anything in Asia. Sometimes if you get lucky at an internet cafe a computer will have Itunes with some songs on it for you to upload. You have to have luck on your side for this to happen, because it does not happen too often. The other option is to meet a traveler that is carrying a computer who has Itunes. Then you can use their computer to upload different songs!
