RelentlessImp's post covers the character's origins.
It's a mini-meme of sorts on Something Awful Traditional Games. When 13 True Ways, a supplement for the game, came out, Sammy's portrait was posted on rpg.net without context or explanation and freaked people out. As a lot of 13th Age fans are Something Awful Goons, the glorious bard's visage was plastered all over the subforum and social media accounts, complete with altered images.