2020 - Didn't carve anything for Halloween (though did bring the pumpkin with me to Atlanta, where I spent Halloween, and back) but the pumpkin was still uncarved as of XRII MMXXI...I had a broken arm at the time, but enlisted Casey Hunt to carve "XRII / #XX / MMXXI" onto it.
2019 - Didn't carve anything for Halloween but the pumpkin was still uncarved as of Thanxgiving so I made pumpkin soup and pumpkin pancakes and carved a turkey into it for Thanxgiving at Lauren & Patrick's.
2018 - I don't exactly remember but I mighta just totally biffed it this year. Pretty sure I at least made pumpkin soup out of the pumpkin I had otherwise bought to carve, though.
2017 - I carved the pumpkin into a helmet to wear on my head. I dressed all in green and my costume was "a vine." Not bad! Got kinda annoying to have a heavy-ass pumpkin on the dome for extended periods of time. I kept carving out a little more and a little more to make it lighter.
2016ish - I was busy, and lazy, and whatever-else was going on, and I never had time to carve a jack-o-lantern for Halloween. BUT I had bought a pumpkin. And the pumpkin I kept for months on end, until early January 2017 came around, and it was good buddy Kevin Stroup's 60th birthday, and for his big 60th party I carved "HAPPY LXth KEVIN" into the pumpkin, which was still totally fine and carve-able and not at all mushy or otherwise showing the least signs of being several months off the vine. The party was on 01/07/2017 and I gotta say I love the idea of a January jack-o-lantern. Who does that!?
2015 - The Flux Capacitor (my costume was BTTF2 Doc Brown from "the future" of October 2015)
2013 - Team Pancakes (as you can see, our team name was carved into it and also it was a storage receptacle for the pumpkin pie raisin spice pancakes I brought both to Saratoga Lanes and to Ross & Kim's party)
2012 - STL Cinemas' logo (it was on display at the Moolah Theatre & Lounge for a few days) and when that one got too ripe, CLOUD ATLAS (the movie the Moolah was showing at the time)
2011 - I made SIX that year: Fishboy (webcomic version)'s face, "Turn/Other" & The/Cheek, King, Kong, and Mag/Net/Ics. All were made for particular concerts (Fishboy @ PPHQ, Turn The Other Cheek Burlesque @ Handle Bar, and KKM @ Upstairs Lounge)
2010 - Eric Von Damage With A Macaw Eating His Head, an artistic interpretation of the photograph on the back of this Pancake Platter
2009 - Billy The SAW Puppet
2008 - Mayor McCheese Campaign
2007 - Lurch from The Addams Family (no salvageable pictures taken, weird!)
2006 - Rolling Stones Tongue (see userpic)
2005 - Award-winning Unicorn Head
2004 - Scuba Diver (there were some pictures on Ron's old Webster University server space but I believe that's all gone now) (Courtney did an underwater scene with fish and reeds to complement)
2003 - Schroeder (of PEANUTS)'s Face (Courtney did Lucy wearing a witch's hat)
BEFORE 2003 - I guess I wasn't regularly doing Jack-O-Lanterns for a few years, and before that, who knows?