On May 19, 1995, O'Rourke and his friends sneaked under the fence at the University of Texas at El Paso (UTEP) physical plant, and were arrested by the UTEP police for burglary. He stayed in jail overnight and posted bail the following day. He was initially charged with burglary, but UTEP decided not to press charges. O'Rourke was arrested for drunk driving after a car crash on September 27, 1998. The charges were dismissed in October 1999 after he completed a court-recommended DWI program.