In the late ’90s, pop-culture historian Bill Geerhart had a little too much time on his hands and a surfeit of stamps. So, for his own entertainment, the then-unemployed thirtysomething launched a letter-writing campaign to some of the most powerful and infamous figures in the country, posing as a curious 10-year-old named Billy.

To his surprise, replies soon started pouring in. Everyone from Dick Cheney and Donald Rumsfeld (on tree-fort diplomacy) to Oprah Winfrey, Mister Rogers, Janet Reno, and members of the Supreme Court had words of wisdom for Billy. (”I like the Egg McMuffin,” wrote Justice Clarence Thomas when asked about his favorite McDonald’s food. “Actually, I like almost everything there.”) Responding to Billy’s idea for a “Hustler for kids,” Larry Flynt wrote back encouraging the fourth grader to “Hang in there. You’ll be 18 before you know it.”

As it turns out, no group hates to disappoint a child more than convicted killers, all of whom responded promptly to Billy’s questions about dropping out of school. Their letters, published here for the first time, range from criminally insane to downright sensible, offering snapshots of the personalities behind some of America’s most hideous crimes. Recently, Radar asked Billy to follow up with his mentors as a college student. (Click here to skip ahead and read Billy’s correspondence with Arnold Schwarzenegger, Larry Flynt, and other non-murderous celebrities)

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