I think what surprised me about #1 was more the time period and the way you had Jon be different from Jonathan, but still similar.

I think a lot of stuff is open to interpretation in The Colbert Report world. Sometimes I like taking everything at face value (like Stephen being able to trap people under his desk or the existence of a time traveling brandy thief) and sometimes I'm more in the mood to think that "Stephen" just faked those things the way it works in reality. That's what's so fun about exploring this world, and I think your story captured that perfectly. And a Mad Lib is the perfect metaphor! :D