I'm really torn about this! There are scenes I really love, and scenes that I just didn't think worked.
I think it's clumsy with some of its musical numbers. Take the bank number: The guy says no, then we get a song about him saying yes. I guess the fantasy is just, "I wish he said yes?" But that's hollow, and it kind of goes across the suddenness with which it hits in the story. The song comes about 20 seconds later than it should - this should be Martin anticipating the yes, praying for the yes, fantasizing about how good the yes will feel... until the fantasy is punctured by the no. But instead, it's just a song and dance - a good one, and funny! - for the sake of having a song and dance. That's not generally how really great musicals work. The final musical number shares the same flaw - it shows us something then gives us a fantasy contradiction, not realizing how much more powerful it is to have the fantasy punctured rather than letting it linger.
But then, the bar segment is great, particularly the crassness of his compatriots deflating his fantasy despite his own crassness within it; he has wildly different standards for everyone else than he is able to hold for himself. As Amy recognizes, he genuinely believes that he's good. He's a romantic in the moment, a lover, someone who can support the homeless, but he's also a someone who stays with his wife for a record store, threatens a homeless man, a date-rapes a girl who might like him.
I also disagree with Devin's assessment that the ending is random. To me, the ending - Martin being hanged for a crime he didn't commit - is essential. He's a guy who did awful things, who shat on everyone around him, the sort of 'nice guy' who constantly shares MRA memes on Facebook, but who is handsome and charmingish-enough to lie his way out of most scenarios and feckless enough to abandon those he can't lie away. So the universe destroys him with something he didn't do, but that his lies and running make him look guilty of.
I think the movie recognizes how scummy and shitty Steve Martin's character is, but I think it wants to takes its time to really show it to us. His first scene shows him as an idle dreamer, and while it's also kind of scuzzy and misogynistic, we see that exact scene played straight a thousand times to show the lead as unfulfilled at home thanks to a frigid wife. She won't support his dreams; how could he not cheat, especially with an innocent schoolteacher? Sure, he kind of stalks her, but that's pretty standard romantic comedy behavior, right? And yeah, their first sex scene leaps right over the edge of sexual assault to me, but maybe it's setting up a redemption arc for him?
But it isn't. He just keeps getting worse. He just keeps destroying everything he touches. And the movie gives him out after out after out, nigh-infinite opportunities to realize that the only problem in his life is himself, but he just doesn't have the sense or maturity to take it. Hell, when the blind girl dies, he immediately realizes he should go to the police, Eileen tells him to, and he chooses to try and hide instead. But even there, he's undone by wanting to fuck in a car.
Ultimately, I think I have to lean for a very soft no. It's a solid deconstruction of the musical with a post-70s edge and a Steve Martin just getting used to stretching himself... but literally everything it did was done more ambitiously, smarter, and better-looking 2 years earlier by Bob Fosse in All That Jazz, even up to the ending. I think the last 5 minutes in particular are where Pennies from Heaven loses my vote, honestly.
I totally get loving an ambitious mess, and I'm glad I watched this, but - at least on first viewing - it leans just a little harder on the 'mess' side than I'd like. But these sorts of movies often improve on second viewing, and this one might too. Just, you know... not in time for voting.
Sorry, Amy. You made some great arguments, though!