Well, there was the retake where the photographer, rather than ask me to take my glasses OFF, tilted them so I looked drunk or stoned. And my sister's hair that would never stay put. And the baby/daycare picture where they had to bribe my child with a random block to get her to sit still. And the home haircut (not by a parent) that everyone seems to have one of...
My worst photo, though was senior pictures. The girls in charge of our section screwed up the whole senior section and did not use people's retakes. My yearbook photo is HORRIBLE. My only consolation is that anybody who sees me now will say, "Wow, she looks great!" Well, that and I know at least one of them dropped out Feb of our senior year and didn't even graduate. I will take my ugly picture and my diploma, thanks.
ETA: Senior pictures for SD - she wore a cowl necked shirt and in one of the proofs it was a tad revealing. She also had a bad 6th grade photo. My DH sees no use in sit down portraits. He says they are overpriced (agreed) and often not the best. I like having a few around, but getting HIM to sit for one is a pain in the butt. SS is no better. They use picture day for the yearbook and the school ID but he hated them every year. One year he actually ripped them up. No more prepaid for us.
Just recieved DD's photos. Locally, they give you a bunch of photos and you pay for the ones you want. A waste, IMO. And expensive! So I get to choose between the one where she has a cute smile, but they gave her a double chin somehow, the full body pose where her face is totally "just take the picture" with a fake smile and the one where she's probably talking. Oh, and she goes to preschool every day, but they only included the class photo from the day she was assigned to take her picture. I called to see if we could get the other set of kids, too.