I just started pin collecting/trading about a month ago, so I don't have much. Right now, I have only 2 Jessica pins - 1950s Jessica and 1980s Jessica - with a few more on my wish list.
The three Jessica pins that I really really really want are - Jessica as Esther in Meet Me in St Louis (my most wanted Jessica pin), 1920s Jessica, and the All Dressed Up Jessica. I love the Jezebel and Breakfast at Tiffany's and Summer Stock Jessica pins too, but those Esther and 1920s and dressed up pins knock out the top three. I've gotta get my hands on that Esther pin! I love the movie and the pin is gorgeous so it makes for a must-have for me.
I'm finding that collecting Jessica pins can be a little tricky though. I've seen quite a few pins where her face, in particular, just looks weird. And that one where she is all in snow, like a snowman, is just bad and frankly, kindof creepy