re: Actors with two (or more) successful careers

Ronald Lee Ermey

Some of these are pretty tough to pin down...

for guys who are popular pro wrestlers and standup comedians, a good bit of the "success" translates over because of their initial popularity. When I watched Eddie Murphy or Richard Pryor in movies, I didn't want or expect deep dramatic performances, I wanted them to be funny. And they were.
Robin Williams really pushed the bubble there, as he became one of the best dramatic actors around, and his standup routines were insanely funny.

Same thing with wrestlers (or bodybuilders); these are big ol' dudes that you expect to be action stars. And with wrestlers, they've already been "acting" with their personas. It isn't a huge leap, going from one medium to the next.
In Bautista's case (and some other fighters/combatants, like Van Damme, Chuck Norris and Bruce Lee), it might take some work to keep from killing people on stage , but again, I've never seen a wide range of acting ability. They're "action" stars. Bautista does come across pretty good with comedy, though.

Musicians are interesting, some could really act, others simply relied on their celebrity.

Actors -> politicians are basically the same angle. You can't deny Reagan or Arnold weren't successful politicians, but they got elected (initially) due to being known and liked. Nobody really cared what Arnold's ideas for running a state were going to be.

Guys like Wayne Rogers, and some others who go into business, law, medicine, or other fields where 'popularity' doesn't matter- that's interesting.

Country western star Jimmy Dean’s hit song “Big Bad John”


The hit got Jimmy Dean a tv show and with his money, he & his brother started the Jimmy Dean sausage brand.

Sinatra.

Jimmy Stewart

Arnold

Reagan

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Arnold Schwarzenegger

Mr. Universe / Mr. Olympia
International Powerlifting Champion
Box Office Star
Governor of California

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Can’t see anyone topping Arnold.

You forgot crazy arse moonbat also.

Brad Pitt was successful working as a fast food sidewalk Chicken in LA before he got famous

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Ken Jeong

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Oh that reminded me, Masi Oka, known for Hereos but also had a recurring role on Scrubs and was on the Hawaii Five-O reboot, started out working for ILM and continued to work for ILM while doing Heroes:

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In addition to his work on the show, he continued to work at ILM up to three days a week as a research and development technical director, writing programs that create special effects.

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And later started a video game studio:

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Oka has turned his digital effects skills to video game production, founding the video game development studio Mobius Digital, where he was a producer on the critically acclaimed Outer Wilds.

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