Google isn't a lot of help. Here are some hit returns from Google (I'll leave it up to you to decide which is the cooler):
How to get this data? Perhap look at the frequency of the word's use on sites focused on entertainment rather than those focused on business (and other serious endeavours)? Or perhaps look at the word's frequency on Twitter (likely to be more "cool" than business)?
Also, it would be useful to assess phrases or word combinations, e.g. "mission accomplished".
...and on the pirate vs ninja debate: