Barry is the drummer for the Unabombers, and is one of the most frequently used altered pictures in animutations. It originated in the first, The Japanese Pokerap, and was frequently used by Neil Cicierega.
From Neil Cicierega's offical guide for Hyakugojyuuichi:
Barry is the drummer for a local band called The Unabombers. Alora is their guitarist’s sister, so she knows them all (these days she’s basically their manager.) Pictures of the band members are common fodder for her MS Paint alterations, and I’ve seen this stretched-neck picture of Barry so much I can’t remember what the original picture looks like.