I can't think of any lies I've told that I've directly benefitted from, but I can think of the most gratifying one I've ever told. About a year after Michael Jackson died, a friend of a friend made a sleeping pill crack about Michael Jacksons death, and I deadpanned "Wait, what? Michael Jackson's dead?" She didn't get that I was joking, and was like "What?!? How didn't you hear about that?" so I just kinda ran with it for a while. I kept making increasingly more boneheaded-yet-obscure inquiries ("Wait, Janet's little brother? The guy from that Moonwalker game? The dude who did that song for the movie Ben?!") until I couldn't hold up the ruse anymore and cracked.