Try spraying the iPod port and cable end with compressed air, or blowing on it with a dry mouth. Sometimes dust ends up messing with the electronic connection between the metal pins.
I would try a few different speakers such as an AUX port in a car, headphones, or a stereo system to eliminate the possibility of the problem being with the iPod itself. Consider replacing the speaker if it's still under warranty - it may be faulty.
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