In February 2011, I became aware that my local paper, the Peoria Journal Star, organized a yearly Oscar contest where you could win tickets to the different theaters around Peoria, IL. At first I thought the prizes would be fairly small, a couple tickets here, a couple tickets there, but I went to the rules webpage and found that the total estimated value of all the tickets they were giving away totaled more than $2000. The biggest prize was 104 movie passes to Willow Knolls, my favorite theater in town. Nothing to scoff at considering back in 2011 I would frequent Willow Knolls pretty much every week (it was only a five minute walk from my apartment).
So there were a bunch of prizes, and in order to win I would need two things: lots of entries and some confidence that I could out-choose the general public.
How does one get multiple entries in this contests? Well, the rules limited the entries to 1 per household, and because I wanted to not break the rules, I would just need multiple households. How to get entries from multiple households? Use your friends! All I would need to do is make my friends aware of the contest, tell them how to fill out the ballot to fit our larger strategy, make everyone agree to share in the bounty, and immediately we have a leg up on the competition, while still staying within the letter of the law with regards to the rules.
After working out how to get multiple shots at winning, how does one out-pick the public on an Academy Awards ballot? I'd need data that strongly correlates with the real probability of nominees winning. What data is readily available and represents the best possible knowledge available on the odds of a future occurrence? Online bookie websites.
Bookies require knowing probability within a tight tolerance, because if they are off, they stand to lose a lot of money in the long term. In early February 2011 you could go online and find out what the payouts are for correctly guessing if "127 Hours" will win best picture. By taking data from many online bookies you can harness their collective understanding and through a little manipulation find the nugget of truth within. This method of utilizing the knowledge of bookies is a useful tool for other applications as well. Bookies won't tell you the future, but they will tell you how much more likely one future is than another, and often do it with a high degree of confidence.
I made a quick and dirty spreadsheet that took data I copied and pasted from easyodds.com and converted that data into usable probabilities for each of the categories. Once we have the probabilities for each category we can come up with a theoretical ballot and come up with the odds that ballot will be correct. It is a trivial task to find the most likely ballot from here (just select the odds-on favorite in every category), but what is not trivial is picking the top 15 or so ballots and determining if any of these should entered by more than one of our 'team'.
Through an intuitive process of determining what deviations (or combination of deviations) are the most likely, I came up with the best 25 ballots and double checked to make sure it was right. The combined probability of the top 7 was about 32% (see the graph below) and the top ten had a 40% of one of those ten being perfect. This is a huge improvement over a simple random selection that only had about a 0.008% chance of getting a correct ballot in 10 tries.
It should be noted that this strategy is only optimized to get the best likelihood of having a correct entry. What we really want is a strategy to maximize the amount of tickets we will win, which may (or may not) be different than what we are doing. To understand this, imagine if a million people all put the most likely ballot in, then if that ballot turned out to be correct than we would only have a one in a million chance of winning any of the prizes, whereas if we played the 8 top ballots, minus the top ballot, we would decrease the odds of having a correct ballot (by about 7%), but the conditional probability of winning in a drawing would go up more than enough to compensate. To find these optimums however, it would require knowing how many people would enter each possible ballot (or at least relative percentage of entries among ballot choices), which is impossible to know. So we just played the strategy that would optimize our chances of picking correct ballots, and hoped for the best from there.
This analysis is a little bit of overkill, but it won us some tickets. The local paper published ther results here, and you can see my friend Allen Chu won 52 tickets to Willow Knolls movie theater the first year we did this. We also won a fair number of tickets in 2012, and 2013 (they did not publish the winners in these years). By 2014 the contest had been discontinued. We continued to enter the local Willow Knolls Movie Theater Oscar contest, but didn't win anything in 2014 and 2015, despite having 2-3 people having perfect ballots. The last couple years there were fewer prizes and a much simpler ballot (fewer categories), so many more people got perfect ballots, crowding us out from winning in the random drawings that resulted.
This shows the limit of the strategy in contests that are overly simplified and overcrowded. Look for contests that have fewer entrants, hard to get perfect entries, and/or have lots of prizes to make it worth your time.
Always check the odds using online bookies when doing an Oscar contest, making sports bets with friends, or if you just want to know how likely something is to happen. They provide their research to you for free, and they back up their findings with cash. Learning how to read betting odds can be pretty useful.