In the late 90s, Bill Geerhart (a grown ass man and pop-culture historian) posed as a little kid and wrote to Charles Manson, the Unabomber, Richard Ramirez and other killers; as well as nonmurderous celebrities like Larry Flynt, Alan Greenspan, Dick Cheney (well, allegedly nonmurderous), Clarence Thomas, and Arnold Schwarzenegger, asking for advice on tough topics like dropping out of school and saving up for a speedboat. Radar Magazine posted their correspondence.
http://www.thecuriouslife.com/?p=76
Excuse my warped humor, I thought it was quite funny.