May attended Clarksville High School, but he told the Arkansas Times he was kicked out in 1990. At the time, he already knew he wanted to spend his life doing stand-up, so when he was suddenly faced with a choice, he said "it was a no-brainer." He was — unsurprisingly — known for pranks, but stealing the principal's car was one step too far. They couldn't prove it was him, he said, but when word got out they were going to kick a whole group out of school, May stepped up and took all the blame.
"The other guys were the valedictorian and the salutatorian," he said. "Those guys wanted college. I just wanted to do stand-up."
Once May hit it big, he was actually invited back to give the keynote speech at graduation. He was psyched to do it, he said, canceling a gig and getting a new suit. But two weeks before he was supposed to appear, the speech was suddenly canceled. The school said it wasn't appropriate to have him back for graduation, but May didn't see it. "It's like, come on, guys, I'm not that little white trash kid you had to be ashamed of. I'd love to come up there for graduation and shake everybody's hands, wish them luck, tell them to follow their dreams, say you can do anything, no matter where you come from."
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