How can I redownload purchased songs from iTunes?

“My hard drive crashed and I lost all my iTunes music, including about $1000 worth of songs I purchased from iTunes Music Store. I’m already stuck re-ripping a bunch of CDs but what about all those songs I paid for? Can I re-download songs purchased from iTunes or am I out of luck?”
Sorry to hear about your data disaster. Losing files is never fun and I don’t envy you having to rip those CDs. Hopefully I can offer some good news for you with regard to those songs you paid for from iTunes. You can redownload music purchased from iTunes, they just don’t make it easy.

The official Apple stance on downloading music more than once is they won’t do it. On the other hand, I know of at least 6 different people and have found additional reports online from people who contacted customer service and were able to redownload purchased songs. The important thing to do in this situation is to submit a polite request via the online form available from iTunes support.
In all likelihood they will take pity on your situation and provide you with a way to redownload your songs. I would also recommend taking an additional step and implement a backup plan. Get an external hard drive and some affordable backup software. I know plenty of people who have lost data because they didn’t back it up the first time – a second time shouldn’t happen.