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Phillips was born at the Subic Bay Naval Station in the Philippines, the son of Lucita Umayam Arañas and Gerald Amon Upchurch, a crew chief on a C-130 in the United States Marine Corps.    His father was an American of Scottish-Irish and one-quarter Cherokee descent, and his mother, a native of Candelaria, Zambales , is Filipina , with distant Chinese , Japanese , Hawaiian, and Spanish ancestry.   
Phillips was named after Marine legend Leland "Lou" Diamond.  After his father died, he took his stepfather's surname "Phillips" as his own. 
He was raised in Texas, where he attended Flour Bluff High School in Corpus Christi , graduating in 1980. He graduated from the University of Texas at Arlington with a BFA in Drama.