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The smallest is this one: Pin 6749: Tiny Pluto HeadIt is smaller than a dime and about the size of a nail. Pinpics would not let me copy the picture to show you.
My smallest pin is a little owl pin in the O-Pin House Graveyard framed set, and without a doubt my largest is th 2009 O-Pin House Haunted Mansion Super Jumbo pin. It's enormous! It comes in it's own box!
Smallest would depend on what you define as a pin- I have several of the "fake" pins on the Marie Osmond dolls, and the mini-pins from the "Build Your Own Pin" thing.
But actual pins with posts, it would be one of these:
Ditto for me! I also have pin #4475. And then I also have this pin that has a similar tiny heart pin, about the same size as the coin from #4475. Pin 3876: Donald and Daisy Valentine's Day 2001
For biggest, I thought it would be this one.... Pin 36234: WDW - Pin Route 498 - Super Jumbo Pin - Tree of Life
But in checking the size listed on Pic Pics, this one is two inches taller! Pin 43418: WDW - Happiest Celebration On Earth - Cinderella Castle (Super Jumbo) #2