hmm... i know it's silly, but have you tried with a different set of headphones? the problem might be the headphone jack itself. another thing to try would be to hook up a male-male headphone cable and check the positive/ground wires for a voltage with a multitester. you will probably find that nothing is getting through, but you never know. do you have a virtual machine on your mac? if so, is it able to get sound out through the headphone jack?
i'm just coming up with abnormal stuff here, because the normal stuff is done. you might try finding the sound configuration files in the operating system and seeing what they show.