Christmas Eve Puzzle: Guess the Book!

I have a tradition with my brother. He likes to figure out what's in his Christmas presents, so I give him a book. Unable to figure out which book just by shaking and groping it, I give him clues to the plot, subject and title. It's also tradition that I post all the clues on this website.

This year's title is eleven letters long, so you get eleven clues, one per letter. If you're stuck in an airport, bored waiting for your date, or need something to play with your family for the holiday, feel free to guess along. Post any answers or guesses to the eleven clues below. Some years commenters have cracked this together long ahead of Dave.

1. This record company released more of his albums than any other. They deliberately mis-spelled their name, and this is the only letter than appears twice in it. Hint: see 11.

2. One of the first movies he appeared in never made it to theaters because he allegedly destroyed the negative himself. It was sensitively titled "_____ Tom's Fairy Tales: The Movie for Homosexuals " This is the first letter in the missing word.

3. The last letter in the last proper album he recorded with his label, and his second-to-last stand-up album ever. Compilations and anthology releases came later, but this was it, a one-word title referencing a superhero movie he appeared in that same year. He was a villain.

4. He was born in this Midwestern state. It's the most populous. The first letter of that state goes here.

5. This letter occurs three times in the title. This is the first time the letter occurs, though.

6. This vowel occurs twice in the title.

7. He wrote for this sitcom, titled after its two main characters whose names both started with the same letter. That letter goes here.

8. This is the first letter in a drug he was famous for doing. It's not much of a hint given how many American entertainers have done it, but few set themselves on fire while under its influence. He was a trailblazer.

9. Comedy Central once spent three hours by counting down the hundred greatest comedians of all time. This is the first letter in the number of where he ranked. Hint: he was in the top seven.

10. If a cop asks if you've committed crimes before, they might ask if you have any "prior ____." This is the first letter in the missing word.

11. This record company released more of his albums than any other. The first letter in their four-letter name goes here. The letter also occurs twice in the name of his home state.

Happy guessing!