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Based on what I have seen I do not think Jay Leno is a Hollywood Liberal. First of all, he grew up outside of Boston. He lives part of the time in LA. The other part in Newport, RI. He has been married to the same woman for 44 years.

When he was on the Tonight Show he told jokes about all sorts of politicians. Not just Republicans.
His Jay Walking segments on the show basically made fun of STUPID LIBERAL Americans. Basically dumb people.

He owns literally HUNDREDS of classic cars. So many that he opened a museum of them in RI. HE actually works on those cars himself. Which is where he got burned when the fuel from one of those classic cars ignited when he was working on the engine. There are several videos on YouTube of various people touring his garages.

I just listened to an interview about this fall this morning on the radio. He said he decided to walk down a hill (he is 78) instead of taking the long way around. He fell and tumbled to the bottom where he hit his face on a couple rocks. He made a joke about it being an old man he should have known better.