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I am seeking to 'rip' an MP3 file from an audio cassette. I own an iMac DV. I'd appreciate anyone's advice as to how to do this.
As far as I can understand, MusicMatch Jukebox can handle the software end of things, and a copy was bundled with a purchase of my CD-RW drive. So hopefully, that should take care of that end of things. (However, if anyone is aware of other software alternatives, including freeware or shareware, I would appreciate you advising me of same.)

Where I am really running into difficulty, however, is the hardware end of things. I own only two audio cassette players. One is a Sony stereo which has absolutely no line in/line out plugs. The other is a Walkman. What I would like to do is figure out some way to have the Walkman play the tape, and have it run into the iMac's microphone jack. (Am I misunderstanding my hardware, or is that the only 'line in' for the iMac DV?)

A visit to Radio Shack indicates that will be problematic. According to the technician there (who could, granted, be misinformed), the jack that the Macintosh uses for its 'line in' is fairly atypical, and he doesn't have anything that could assist me.

Has anyone been able to successfully rip MP3s from cassettes using an iMac or Macintosh? If so, can you advise me of how you did it, both in hardware and software respects? Any specific advice for this situation?

The guys at RadioShack are among the brightest young minds our nation has to offer. But they should have sold you a plain old stereo 1/8 inch (miniplug) cable (miniplug on both ends...also known as 3.5mm). That is, I assume, what you need to get signal out of your Walkman. The other end will definitely work on the Mac.

Then, go to download.com and search for 'Coaster', excellent freeware recording software. Record stereo aiff at 16 bit and 44.1kHz.

Search for iTunes at download.com also. It is free for all Mac users and will convert your aiff files to mp3.

You are welcome.