All credit for this contest idea goes to @Freamwhole from Zed to Zed, the website and podcast dedicated to achievement hunting. He's got a similar contest going at the site, and I'm straight up stealing the idea.
Here's how the contest will work: I will post 12 different categories below. Starting May 1st through May 31st, any achievements/trophies (from now on, I'll refer to them as A/T's) you unlock that fit the requirements of any of the categories can be submitted. You'll receive entries into the contest based on the gamerscore of the A/T (If a trophy for a PS exclusive game is used, it will be scored 10 for bronze, 30 for silver, 100 for gold, and 200 for platinum. If the game is available on both XB and PS, the score will reflect the XB gamerscore, with the exception that platinum trophies will always be worth 200). If you are the only person to submit that particular A/T, you'll get the full score. If multiple people submit the same A/T, score for it will be divided between them. For example, you submit a 20 GS achievement for the first category, and are the only one to submit it, you get 20 entries. However, if 5 other people also submit it, each person will get 4 entries (20 divided by 6= 3.33; I'll always round up) To keep entries secret, you'll submit them to me via pm, not in this thread. You'll want to be registered on trueachievements.com and/or truetrophies.com so you can send me links to the A/T's you unlock as your entries.
For example, if one of the categories was "Unlock an achievement that has a word with double O's in it, such as "book", "look", "balloon", etc.", you could pm me a link like this.
UPDATE: A couple quick things I forgot to mention. Please only submit one A/T per category. If you find several A/T's that fit a particular category, that's great, but you have to choose just one to submit. Also, you don't need to submit them as you unlock them. The deadline for unlocking them is May 31st, but I'll give people until June 7th to get their entries organized and pm them to me.
IMPORTANT NOTE ABOUT ENTRIES: A/T's can only be submitted for one category, even if they qualify under more than one. For example, if there was somehow an A/T titled "Dad, would you please pass the big tub of popcorn?", it would qualify for category 2 (question), 4 ("pass"), 5 ("Dad"), 6 ("Big"), 8 ("Big"), 11 ("Popcorn"), or 12 (ten words), but you would have to choose just one to submit it for.
Here are the categories. You don't need to complete them all; you can enter the contest with a single A/T unlocked from any of the categories, but the more categories you unlock, the more entries you get.
1. Starvin' Marvin- Unlock an A/T with a 2 word title with words that rhyme.
2. Do the Handicapped Go To Hell?- Unlock an A/T with a title that is a question.
3. ManBearPig- Unlock an A/T that has a mammal in it's title.
4. Sarcastaball- Unlock an A/T with a sports-related word in it's title
5. Tsst!- Unlock an A/T with a palindrome in it's title (a word that reads the same forward and backward; i.e. "Mom", "Dad", "radar", etc.)
6. The Biggest Douche In the Universe- Unlock an A/T that has either the word "Big", "Bigger", or "Biggest" in it's title
7. Red Badge of Gayness- Unlock an A/T that has a color in it's title
8. The Return of the Fellowship of the Ring to the Two Towers- Unlock an A/T that has the name of a movie in it's title (Keep in mind that lots of movies have one word titles) Your A/T must contain the full title, including words like "A", "An", or "The".
9. Ass Burgers- Unlock an A/T whose title is a pun or a play on words
10. Elementary School Musical- Unlock an A/T that has a music-related word in it's title
11. Royal Pudding- Unlock an A/T that has a kind of food in it's title
12. I Should Have Never Gone Ziplining- Unlock an A/T whose title is 6 words or longer