Starting here, where I pick the winner of 40, that winner will then be THE JUDGE for the winner of the next contest (but cannot participate). After that, the next winner will be the judge of the next one (and the previous judge can then resume participating). Everybody got that? Victory not only nets you a sweet image that you should meme all over the internet, but it also lets you pick out who your followup is!
So with that out of the way, last week's winner was... um... Angel Bob from accounting!
Hah, I'm kidding. Nobody likes Angel Bob. No it was a tough choice between blsedbx3 and Lilah_Kane who both appealed to my 90s nostalgia with references. I decided to pick the shorter, pithier one, so congrats to blxedbx3. Make sure you can direct message me on here or twitter so next week you can tell me the winner. (but seriously go check out the song lyrics entry Lilah put in - then make me feel old by asking what it's referencing)
Anyway, the next episode had a buffet of choices and I decided to go with some guys we don't see in this contest often.

Best of luck everyone, and feel free to vote on your favorites anyway just to give your favorite captioneers some love.