My current calendar is the one from Cockeyed.com, mentioned here.
Last year was this Bob Masse collection of concert posters, and 2004 was an “I Hate Cats” calendar by Skip Morrow.
Georgia O’Keeffe
I get a shitload of those Chinese grocery store / business calendars every year from my mother-in-law. We give most of them out but I keep the nicest one for myself.
Whoops, forgot to mention the Racing Girls Calendar calendar! Hot babes and the bikes they race, as opposed to merely standing next to them looking pretty you get with most calendars involving ladies and vehicles 
2005 calendar was the London cast ofl Woman in White, starring Michael Crawford as Count Fosca.
2006 calendar is the Broadway cast of Woman in White, starring Michael Ball as Count Fosca.
On my night table I’ve got a 365 day knitting calendar with little pictures of objects and the patterns for making those. Today’s is a knitted bead bracelet. :eek: (this involves by-gum-are-they-TINY needles and oh-jeez-MICROSCOPIC beads)
The office calendar (once I remember to bring it in) is a Mutts calendar. Yay for Earl and Mooch! Last year’s was that Brian Froud Smashed Fairies calendar – that was fun.
I got many options. My wall calendar at home is from my alma mater.
At work, I have the college academic calendar where I work posted on my wall. My brother-in-law gave me an Onion calendar, not knowing I find the Onion spectacularly unfunny (or rather, never more than a mildly amusing idea streeeetched out until it’s not funny any more.)
Really.
A fire safety calendar from my sister (a per-call firefighter)- contains winning fire safety posters from kids.
I’ll see what the stores have for my at-home calendar-I always wait and get them for 75% off.
Brian
I’ve got several:
At home, on the wall: 365 Kittens a Day (we get a new one of these every year)
At work, 3 desk calendars:
- Calligraphy (complete with a pen, so you can practice on their example each day)
- Cat Fancy (a cat a day)
- German (one German phrase a day–I’m learning the language, so it’s cool)
Bought them all myself (or, in the case of the home one, with the spouse).