How to take music from cassette tapes to iPod

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So I have this large cardboard box full of hundreds of cassette tapes with music I absolutely positively had to buy in the 1980s and '90s. If I wanted to listen to the music contained on those tapes on my iPod, I imagine I could follow a process something like this:

  1. Put new batteries in my old Walkman®

  2. Connect some sort of cable between the headphone jack on my Walkman and the audio jack on my mid-2011 MacBook Air

  3. Play tapes on the Walkman and record the incoming music on the MacBook Air using some sort of software.

  4. Use iTunes Match to upgrade the quality of the resulting audio files.

  5. Put the iTunes Match audio files onto my iPod.

I know this workflow would take a long time (each tape would have to play its full length), and I don't know if it would work.

So my questions is, what should I do? Again, my goal is to get music from my audiotapes to my iPod without having to repurchase all the tracks. The procedure outlined above is just my guess at a solution; if your answer doesn't look much like that process, but it doesn't cost much more than iTunes Match, I'm open to ideas. I'd love a solution that worked faster than my idea.

Best Answer

I'm afraid there is no alternative without playing the full length of the cassette. Since it's an analog signal, you can't just move a file from the cassette to your Mac... If you want to convert your VHS to DVD, you have to play your entire tape too because it's a analog signal.

But I'm sure, since you care so much about the music, you won't bother listen (and enjoy!) the cassettes one last time on your walkman while recording them to your Mac.

I've done this with my collection of cassettes a few years ago, and I must say, it was a true delight to listen them once more with the "cassette noise"! Now I can enjoy this lovely music everywhere I want!
So, do as you thought and enjoy your music!