just be aware that anything that's 'free' is illegal best way to go if he's gonna get a lot is to pay monthly, w/ which you almost always get unlimited downloads for that set price BUT w/ yahoo & itunes at least there's an additional charge IF you're going to burn the song to a cd (transfering to an mp3 player is fine) sites that charge per song will be $0.88 (walmart i believe) & up, sometimes 2 or 3 bucks depending, but this can really add up basically you pay & you have either a set amt of time (a month if that's what you paid for) to dl as much as you want, or you have an account & you're charged whenever you dl a song...itunes is by far the most popular (bc so many people have ipods), but i would research on price vs selection...most sites have millions of songs best deal i think would be yahoo, which is $4.99/mo if you pay for a year, or $6.99 if you pay month by month, & $0.79 per song you want to burn to a cd http://music.yahoo.com/unlimited/ ive prob confused you tho, try going to that site & read about the service