There is a moment in Henry's Crime when Vera Farmiga is teaching Keanu Reeves how to act. He delivers a line from Chekhov's The Cherry Orchard, terribly, and after some gentle coaching from her repeats the line... with exactly the same delivery. A smile breaks out over Famigo's face as she realises that her struggling play has found it's lead. "Wow" she gasps "You're a natural" leaving Keanu smiling and the audience puzzled over what exactly happened.
This may give you an idea of why Henry's Crime doesn't work.
The premise of this baffling mess is that Henry (Reeves), having been sent to prison for a bank robbery he didn't commit, decides that if he "did the time he may as well do the crime". After discovering an old tunnel running from the bank to the next door playhouse, he enlists the help of fellow jailbird Max (James Caan) and the two decide the only way to access this tunnel is to get Henry the lead in The Cherry Orchard. I'm sure you can see the cracks in this already and the cracks start and stop with Reeves.