HW is a mix of George Carlin, Dr. House, Hunter S. Thompson and Sgt. Hartman.
None of which could get elected to any office. Also, George Carlin was a very liberal atheist, as was Thompson.
Oh hush this would be hilarious. Plus if they were Christian there'd be no real issue if they started small, particularly George Carlin (NYC shouldn't be too hard for a Democrat) and Thompson thought about a run for senate, right Cathcon? I know he didn't win, but how did that turn out (if I'm right that is).
From what I remember reading, there were three positions Thompson either aspired to, ran for, or considered running for.
One was Sheriff of Aspen on the "Freak Power" ticket. He lost by a comfortable margin in a two way race. It was two-way since the Dems and Reps decided to team up to make sure that the Freak Power slate of candidates didn't win a single office.
Second was American Ambassador to some island country. Can't remember. He made several references to it and being told that he would get it then later being disappointed. ("He tells me to go out and by six white shark suits. Then that fu
cker tells me not to get my hopes up!")
Third was Senator from Colorado in '74. He considered it in some of the post-'72 election haze. He talked with Gary Hart about it and it turned out Hart (who had helped run the McGovern campaign) was considering it. He later gave it up entirely.
Now remember those three accounts are according to Thompson himself, so he's not the most reliable narrator. So this page casts a tiny bit more light on his run for "Aspen Sheriff" which apparently was for something else.
Thompson's "Our Campaigns" Page