Watson grew up in poverty outside of Pasadena, Texas as one of four boys. Watson's father and brother Jim were both musically inclined and guided what have become his longstanding musical influences. Watson began writing his own songs at age 12, making his first recording two years later. By day he went to school and by night he played local Houston clubs and Honky Tonks with Jim in an aggregation called the Classic Country Bandin. He moved to Los Angeles in 1988 on the advice of Rosie Flores and soon joined the house band at North Hollywood's now-legendary alt-country venue the Palomino Club. Not long after, he moved to Nashville and spent some time writing songs for the Gary Morris publishing company where his first daughter was born. Watson relocated to Austin, TX, where he formed a backing band called the Lone Stars. He released his debut album, Cheatin' Heart Attack, in 1995. It was greeted with enormous acclaim for the vitality Watson brought to his vintage-style material and performances and also featured a dig at mainstream country in "Nashville Rash.
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