Stuff you'll need:
Soldering Iron [optional, recomended for best results]
Solder [likewise]
A replacement headphone plug. I recomend:
this but anything similar will work. (be sure to get 1/8" no 1/4" stereo!!)
A wire stripper
A lighter [optional]
Electrical Tape [optional]
I'm leaving for work soon, but later on I'll post some pictures.
Headphone jacks that come with devices always suck. Especially when they are in the L shape. I've done this repair more times than I could count.
1.) The repair is actually quite easy. First, take your wire stripper (or cutters) and snip off the entire faulty plug. Throw it out.
2.) Assuming you are using the connector I showed you from radio shack... Unscrew the device. You should have 4 parts. The outer housing, a spring, a slieve, and the jack. Note the order how this should be assembled.
Take your brand new connector and slide onto the wire (in the correct direction, and in this order) The outer housing, the spring, and finally the plastic shield (if it comes with one). Slide that far away from the end, as it will just get in the way later.
3.) Split the 2 thick black wires apart about 3/8 of an inch.
4.) Take your wire strippers (or use your finger nails) and strip off about half of the black rubber coating. Inside you will find 1 of 2 things: 1 un shielded copper wire and 1 shielded (either white or red), or 1 un shielded copper wire and 1 kinda painted copper wire. (if it turns out that inside each black wire, you have 2 shielded wires, then awesome.. You've got some serious headphones... )
5.) On each wire, take the unbraided, unshielded copper wire and twist it into a new straightish piece. For the other, either strip off a little bit of the plastic coating to reveal the wire inside (and then twist that into a neat single wire), or use a lighter to burn off just a bit of the painted part. If you used a lighter, let it cool for a moment and run your fingers on it to remove the black soot.
6.) Take the 2 original grounds (the ones that were unshielded to start, or were the same color in the black wire) and twist them together. Do not twist the signal wires together (the red and white, or red and green (or whatever color the designers used)).
7.) Bring over your replacement end. You will notice 3 prongs with small holes in them. The one that sticks out the furthest is the ground. The other two are signal. I'm not sure which is left and which is right, but it doesn't really matter.
Attach the twisted pair of ground wires to the hole in the big prong. You can twist it tight if you don't have a soldering iron.
Attach the other two to the signal leads in the same fashion. If you need to, you can bend them out temporarily to do the work, then gently bend them back in.
8.) Place the black wire over the clip at the end of the big prong and using the plier part of your wire strippers, crimp over metal tabs to lock the wire in place. Don't make it too lose where the wire will be able to fall out, but don't do it so hard that you may damage the inside wires.
9.) Make sure none of the leads touch eachother!!! Otherwise you'll have a dead left/right side(s).
10.) If you had a plastic slieve, bring that down over the work area. If you don't have the slieve (or lost it) wrap the work area with about an inch of electrical tape. You can optionally wrap the leads separate to ensure there are no shorts between the wires. Then follow up by twisting on the outer housing. Screw down tight and then test to see if they work! =]
Thats it.