Having been in many of them myself, I have to admit that I'm a sucker for a bad high school yearbook photo.
Planet Dan has some hilarious pics he's gleaned from various annuals. The captions are pretty funny, too.
He writes: "I remember when I got my senior picture taken and I brought my stuffed Hershey's Kiss, I at least wore an outfit to compliment it."
"Very tasteful."
"Maybe she's shy, or just really really ugly."
"A pose that any mother/gay porn director would love. (p.s. he's a Bears fan)"