Since he was a kid, Jack grew up on hard boiled crime fiction. He always imagined himself to be the tough protagonist in those books. When he is thrown in one of those pulp fiction situations at the age of 29, with tough guys, big dough, feminine dynamite and exotic romps, his perceptions about his masculinity and toughness is about to change.

Firstly, I agree with Karel, this is an interesting concept- a chance to strip down the hard-boiled detective genre. (Of course that’s not the route you have to take.)
But the logline needs to be polished up.
-Make sure that the logline is a single sentence even if you have to use complex/compound sentences. -Secondly, it will add a lot if you mention what the protagonist’s profession is at 29. The tone and the dilemma will drastically change If he’s a comic bookstore owner or a druglord or a doctor. Add that layer in here.
-Instead of saying “tough guys, big dough, feminine dynamite and exotic romps” use that space to tell us more about the exact situation that gets him in that position. Is it a case of mistaken identity? Did he get himself in trouble on purpose? Is he framed? That’s more important. Once you say he’s in the world of the pulp fiction stories he once loved as a kid it automatically entails that there will be the elements of the noir world.
-This logline doesn’t necessarily bring across the tone of the film. It can be a serious noir thriller or a comedy on the line of North by Northwest. Make sure the tone comes across when you frame the logline.

I know it sounds like a lot to bring in with a single sentence but it’s possible. And personally I like working and re-working on my loglines because sometimes a few words changed here and there gives a whole new exciting direction in the actual story that you’d never have thought of on it’s own.

Good luck.