Check out the Will Rogers Writing Contest. If you can write Will Rogers style, you have a chance to win. Write a 500-750 word essay of commentary, humor, human interest, or a brief (not your underwear). There are examples of each on the website.
Entries must be received by October 1st, so mail early or take the easy way and email.
Prizes: First Place $200
Second Place $100
Third Place $50