Should you sue someone is small claims court who have felonies on his record?

Small Claims court is a civil court. Not criminal so a felony record has no bearing on the court. There are two types of court. Criminal which handles actual crimes. And Civil court which is a court of contracts. They handle all types of cases that deal with agreements between two parties. Check your state/province to see if max claim amount you can make in small claims.

If you believe the cost is enough to go through the courts to get, is enough. Then do so, regardless of the others history. One driving without insurance, on a suspended licenses, probably doesn't have anything. So you'll be trying to get water from a stone anyways.