Should I be able to play my ipod connected via a 3.5mm analog in?

So I have a 3.5mm male to male connector. I connected my ipod to the audio in jack on the mbp. When I play music from the ipod, I don't hear anything from either the internal speakers or a pair of usb connected speakers...
Is this configuration suppose to work?

The "line in" on an MBP is just that - an audio line in, which 'expects' line-level input. The headphone output of the iPod does not have sufficient power for a line-in port. A microphone port (which the MBP does not have) is what you'd need, or an amplifier. Since the MBP is a 'pro' computer, the line-in port is designed to work with audio devices which provide line-level output.
Having said that, there's no need to use the headphone port to play the music from the iPod. Just connect the iPod to the USB port (via a dock connector). Do NOT sync it (decline the option if offered), select the iPod in the devices list on the left side of iTunes, tick the box to "manually manage music..." Then, click the little triangle to the left of the iPod in the devices list, and you'll see your music. Click on a playlist, then double-click on a song in the main window to start playing it.

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Should I be able to play my ipod connected via a 3.5mm analog in?

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