What do I do if a lien holder won't sign the lien release after I pay the lien?

You still have the receipt for the money order - yes or no? If yes, contact the sheriff’s office in your locale and see if they can help. If no, then you are up the creek. The title should be in your possession, not his. You were simply naive in this transaction and your “friend” is an SOB who is taking advantage of you.

In the future you should get a separate bill of sale for any major purchase such as a car. And you should have the title with the name of the lien holder on the title. Sometimes a bank or a leasing company will hold onto the title, but never another individual.

If you are listed as the “owner” on the current title, then the “friend” can’t sell the car without forging your signature. Forgery is illegal, but perhaps not beyond what this friend might do. You have the car and he has the title and neither of you can do anything (legally) to sell the car. If you give up possession of the car under intimidation then you have zippo. Hold onto the car. Document the $200 money order made out to the seller, and seek legal help.