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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.

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  • I doubt that step four will work. There's metadata missing that iTunes Match needs in order to match songs.
    – gentmatt
    Commented Mar 16, 2012 at 13:15
  • Is it metadata that can be added?
    – Daniel ♦
    Commented Mar 16, 2012 at 13:17
  • I don't know what the minimum requirements are for iTunes Match to match a song. But I've had cases where songs were not recognized just because the rip was a bit longer.
    – gentmatt
    Commented Mar 16, 2012 at 13:22
  • I've asked a new question to focus on the issue of iTunes Match and analog sources, specifically. apple.stackexchange.com/questions/43903/…
    – Chris W. Rea
    Commented Mar 16, 2012 at 14:35

3 Answers 3

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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!

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  • Does the full-length song need to be in the file for iTunes Match to correctly identify it, or if I get, say, the first two minutes, would it still positively identify?
    – Daniel ♦
    Commented Mar 16, 2012 at 13:21
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    I'm not sure. It depends on the meta data I guess. I just cut a song in half and matched it with iTunes and the full song showed up on my iPhone... So I bet it's really depending on the meta data (which you can add by yourself apple.stackexchange.com/questions/31227/…)
    – Michiel
    Commented Mar 16, 2012 at 13:25
  • @DanielL you need enough of the song for the signature to be generated. Usually it's based around a sample from a portion of the music with a fairly high power level. It's probably easiest just to let software import all of the songs. There also may be a time length sanity check on Match so it cannot be gamed.
    – Ian C.
    Commented Mar 16, 2012 at 13:25
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    @Michiel That's amazing! I didn't know that this is possible.
    – gentmatt
    Commented Mar 16, 2012 at 13:35
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For step 3, I'd recommend Rogue Amoeba's Audio Hijack Pro which has the ability to break up the incoming audio into tracks for you and import it directly into iTunes.

But otherwise, you've got to do pretty much exactly what you planned to do.

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There are a number of cassette tape decks with USB ports on them now that can make this process a little smoother. The advantage to going with a USB-enabled deck is you don't have to worry about output levels. Or more specifically, you don't have to worry about clipping the input to your Mac with a too hot analog output from the tape deck.

With your approach you'd need to scan every tape, look for the peak level, and make certain the output level of the deck didn't clip the input when it played through that peak level. That's a time consuming process. The USB-enabled decks let you gloss over that.

Looking around, it appears that ION makes the most popular line of decks for this purpose, thought I can't personally speak to their quality. It is listed as plug-and-play on Mac though their minimum version is 10.4, so I'd check with them to make sure they support the CoreAudio changes in 10.7.x before buying. They make software that will connect to the deck and automate the extraction and splitting process for you. It doesn't mention if the software can play the tape back at a fast-than-realtime speed. Probably it cannot. So your transfer is going to be limited to realtime.

Once it's in iTunes, Match should do its thing and upgrade the tracks.

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