Luckily, the majority of my parental embarassment came at only one time of the year - Christmas! My dad used to (and still does) wear a Santa cap everywhere he went for most of the month of December, and has carols playing on his outdoor speakers at all waking hours, and overnight of Christmas eve. He would always pick up the bargain bin Christmas albums put out by whatever band was hot a few years ago... last year he got New Kids on the Block and Rita MacNeil (a little Canadian joke, there).
My dad is also a serious amateur photographer, so every time I turned around, he was taking a picture of some minor event in our lives - every dance, every party, every date (I didn't date much, so it was an occasion
, Easter, Thanksgiving, Christmas we had to pose, lined up tallest to shortest. It is quite amusing now that my brother and I are grownups, you can't tell one "event" from another by the pictures, unless Mom and I can remember when we bought a certain dress.