Not sure whether this is relevant to the thread, but I think of Mark Wahlberg who went from being a Calvins model with leaked cockpics from the shoot, and bro of NKOTB singer, and we never heard from him again .... or didn't he do Boogie nights and then Ted.
And then Sebastian/Simon Rex - known as an MTV vjay in the 90s and then in a few faux horror movies. With this guy (a) his porn shoot was innocent, cute, and really hot. He should be proud of it. (b) MTV was an idiot for dropping him. (c) He made it to the movies. good for him.
Why the resume gap? you were in the movie industry making low budget movies. Why wouldn't you pursue your dream by starting at the bottom, and then admit to yourself that you couldn't make it to the top?
The closest I get is someone who was on the cover of TheGuide travel (formerly magazine). It's modelling, not porn.
Watching election crap right now - I would imagine Jeb Bush's dickpic would be widely available if it were floating around. I doubt anyone would care about any fortune 500 ceo from 30 years ago (and dick and face wouldn't be recognised). unless you are planning a political career, I don't think it matters. The movie boogie nights addresses this when Julianne Moore goes for a job.
Back to this being pics of famous dicks.