Last year I was honored to work as an Assistant Producer of the 27th annual National College Comedy Festival at Skidmore College (as all student producers of ComFest do their Junior year). To learn more about this comedy festival that changed my life you should visit its website, or read the cool New York Times writeup about it from a few years ago.
As an assistant my job was primarily running errands that the busy producers Hannah and Boco couldn't get to. Luckily for me, the producers also entrusted me with designing and illustrating art for the festival's promotional and merchandise materials. This was a dream come true for me, although I encountered a couple of obstacles along the way that helped me grow as a versatile designer. Most notably, my first drawings were of things I felt conveyed "comedy" or "college," but all felt too cliche or (ironically) unfunny.
Eventually I got on a roll of drawing things related to US Presidents. My thought was: instead of starting with the "college" or "comedy" component of the festival, why not start with "national"? Every year the festival brings about 14 different schools from all over the country to Saratoga to perform comedy. So, after several different ideas and iterations, I landed on this two-tone illustration of Mt. Rushmore decked out with comedy/party props.