In the diner one, the actor talking to The Messenger is Lex Medlin ("Happy Hour"). The waitress is Kate Micucci ("Raising Hope"). The actor playing The Messenger is remaining nameless right now...
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No. Two different guys. "Keith Stone" is actor Mitchell Jarvis. The Progressive guy is actor John Jenkinson.
The same guy as what? If you are referring to the other guy in the commercial, then it does appear to be the same guy.
Just a guy who likes savings and pie. His name is John Jenkinson. The girl who asks him who he is, is Kate Miuncci who is in Garfunkel and Oats.
Paul Whitehouse
The Bald Guy is Martin Fortier. The Asian Guy is Russell Yuen.