I just used the site
yearbookyourself.com to create some pictures of what I might look like in yearbook photos from different years. Here are some of the best ones:

1952

1960
(I think I look a lot like my grandma in this one.)

1992

1994
(As I recall, my actual hairstyle in that era wasn't all that different.)
I just have one thing to say about this: BWAHAHAHAHA!!!