The Jackass Regatta is an annual event that occurs in Olcott, New York requiring participants, with strong character similarities to pirates and vikings, to race two per canoe, and drink nine beers each on a one mile voyage to their bridge and back. This event was started initially by two great friends, Bob and Tom, (not sure when, but probably a very long long time ago- as it became wide spread tradition long enough that it required t-shirts and memorabilia), and then was passed on to their sons to carry on that tradition. While working for Daytona Sportswear, I had the good fortune of being introduced to this wild bunch of people, never short on jokes and always super fun to work with. I was privy to the mayhem in my Florida office by way of phone calls and funny emails and set to task to recreate the shenanigans. This is what that looked like in a sample time line of their shirt designs: from the first rather rough design I did for them in 2007, (please scroll thru to the end – they get more fun as you go along) and the very wild and crazy designs that followed over the years. I also included some “how it was made” images and a few close ups.