(Disclaimer: I am not affiliated with the Sidewise Awards or any of the individuals associated with presenting and maintaining the prize. I am a just an alternate historian who appreciates what they stand for. Some of what I might say could be misleading or false. I based these answers from what sources I have been able to find on the Internet.)
What are the Sidewise Awards?
The Sidewise Awards for Alternate History are an annual award given out every year at Worldcon for the best alternate history publication of the previous year.
What are the categories?
There are two major categories, the Short-Form Award and the Long-Form Award. Short-form works are those publications under 60,000 words and long-form is for publications over 60,000 words. There is also a special achievement award that is given out occasionally.
What are the requirements?
All works must have been published in the English language the year prior to when the awards are presented. Thus if a book is published in 2014, it won't be eligible for the Sidewise Awards until 2015. There is some wiggle room on this requirement if the work was published outside the United States, but wasn't available there until much later.
How is a short story/book nominated?
Review copies need to be submitted to all of the judges. These include friend of The Update Steven Silver and well-known author Stephen Baxter.
What does "Sidewise" mean?
The Sidewise Awards take their name from Murray Leinster's "Sideiwse in Time", which introduced the concept of travelling between alternate realities to pulp fiction.
When will the next Sidewise Awards be announced?
The 2013 Sidewise Awards will be announced at Loncon 3 on August 16th at 8 pm. It will not be live-streamed.
Why wasn't [insert book title here] nominated?
I don't know. Perhaps the judges didn't like it, the author never submitted their work for consideration or it was ineligible due to when/where it was first published. Direct all inquiries to Steven Silver (shsilver at sfsite dot com).
What about games, film and TV? Why aren't they considered?
Again, I don't know. Go ask Steven.
Why should I care?
As far as I know there are no other organized awards that celebrate literary accomplishments in alternate history. AlternateHistory.com and the AltHistory Wiki both have their own awards, but they are informal and focus only on the accomplishments of the members of their community. The Sidewise Awards focus on the professional literary side of the genre and help identify the best works of alternate history ever published. You can't go wrong by recommending a Sidewise winner (or even a nominee) to someone when they ask for a book recommendation.
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Matt Mitrovich is the founder and editor of Alternate History Weekly Update and a blogger on Amazing Stories. Check out his short fiction. When not writing he works as an attorney, enjoys life with his beautiful wife Alana and prepares for the inevitable zombie apocalypse. You can follow him on Facebook or Twitter.