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John Mayer in 1990s

Varsity Blues
"I went to school to get it over with," John Mayer, the middle son of Richard (a high school principal) and Margaret (a teacher), tells ABC News in 2003. "I remember asking my mom, 'Mom, will you please let me drop out?'" (He'll later capture that angst in his breakthrough hit, "No Such Thing"). After graduation, Mayer spends 15 months working as a full-service gas station attendant for $7 an hour, and uses the cash to buy a guitar.