2008
Barack O'Lantern (Yes We Carve.com):

Heath Ledger's Joker from The Dark Knight:

2007
Pale Man monster from Pan's Labyrinth:

2009?
If I end up having time, I'd probably stay with my "movie I've enjoyed that year" theme and do a pumpkin of Dr. Cockroach from Monsters vs. Aliens:
Hm, that was easy. Maybe I'll just Photoshop pumpkins from now on...
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