The Rejected Photo
Senior year of high school I was selected for the February "Student of the Month" award. I needed to submit a photo for the award page. I was working on my Photoshop skills, so I thought it would be cool to hand in the following photo:
The photo was rejected, and the award people just sent someone to take a picture of me instead.
A week or so later, I got accepted to Olin's "Candidates' Weekend." They asked me to email a photo to be used in a prospective student slide show. I sent in this photo... and it got rejected again!