Ever wonder what kind of mentoring advice such diverse personalities as Alan Greenspan and Charles Manson would give a 10-year-old kid who’s thinking about dropping out of school? So did “pop-culture historian” Bill Geerhart, who posed as “Billy” and wrote them both, along with several other notable names.

From serial killer Richard Ramirez, known as The Night Stalker came an odd request for a photo:

Billy,
Greetings. Got your letter. What school do you go to? Who’s your friend? You should stay in school. Send pictures.
Richard

(Ramirez later requested photos of Asian girls… but without “scenery”.)

The Unabomber, Ted Kacynzski, sounded surprisingly sane as he noted “I can’t advise you whether to drop out of school, because I don’t know anything about you…whatever you decide to do, I wish you the best of luck.”

Erik Menendez, who is serving a life sentence for the murder of his parents, apparently has a rather busy schedule in California’s Pleasant Valley Prison but that doesn’t stop him from trying to help a kid.

Dear Billy,
I apologize for the length of time it has taken me to respond. That will not happen again. [...] It is hard for me to imagine that you should drop out of school. Fill me in some more on the details of your life.

I am here and would like to listen to you and do what I can to help you Billy. But I really need to know more about you. No need to send stamps or that sort of thing. Thank you though Billy.
Your Friend,
Erik

When “Billy” wrote to Alan Greenspan in search of advice about the fastest way to save up money for a speedboat, the then-Federal Reserve Chairman was apparently too busy to write back himself. His assistant (who kindly enclosed a photo of the unphotogenic Greenspan) explained in a neatly-typed letter that it’s never too soon to begin saving since “the longer you have to invest your savings the higher the return will be.”

And notorious, freakazoid serial killer Charles Manson’s advice? It’s as freaky as you’d expect.

Find out why the L.A. Times hasn’t sent my newspaper —Charles Manson.
P.S. O-yes HI BILLY
Easy easy EASSY

(Manson also attached the mysterious picture of a barn.)

I bet you don’t remember this —you dont [sic] even know where its [sic] at. HAHA. I got you there.
Charles Manson
Easy BILLY

But things get really interesting when Geerhart writes back 9 years later and tells Charles Manson he not only stayed in school but wants to become a prosecutor. Read it at Radar Magazine and be glad they haven’t let that sick bastard out.