I'm sure it seemed like a great idea at the time. Cross cut between a detective story where a guy digs into the seedy underbelly of Hollywood and the drama of a C-level movie star committing suicide. These are two very different genres that have the potential of getting to the dark side of the American Dream. Some of the greatest movies in film history deal with this theme.
But it doesn't work here. In fact, this story devolves. A quick look at why highlights how important it is to explore your premise thoroughly before you write your script.
The first big structural mistake has to do with the detective line. This one doesn't build its revelations, leading to the biggest reveal of all, who-dunnit. Building revelations are the main reason people go to see detective stories, so that's a pretty big mistake. The detective in Hollywoodland goes through various scenarios. But about halfway through it becomes clear that his investigation is just one big stall. Without the rewards of ever-bigger reveals, the fuel runs out of the desire line. The result: the audience gets really pissed off.
The second structural problem has to do with the second storyline: the drama concerns a person I don't care about. This guy supposedly commits suicide because he can't get any parts other than Superman. That's a drag, no doubt, but Norma Desmond he ain't. A drama about a personal tragedy has to start with a complex character who has great flaws but also has an heroic quality, even when he's Willy Loman. The George Reeves character is bland, with little talent. He doesn't have great flaws. He doesn't have great strengths. Without a complex character to start with, the drama can't build as it explores the deeper issue at the hero's core. So again, the story becomes less, not more, interesting as it proceeds. You can't make a bigger mistake than that.
The third cause of failure has to do with the requirements and expectations of a cross-cut structure. When you do a cross-cut over the course of an entire story, you are highlighting the comparison between the two main characters and the two lines of action. That means that the juxtaposition between scenes in each line must create a greater meaning that only comes from comparison. That doesn't happen here beyond the most superficial level. Yes, both main characters are little men in the hierarchy of LA. Yes, both have personal problems with petty jobs and broken families. But you need a lot more detail than that for a comparison to trigger new insights.
If you want to see how to write a good drama and figure out the structural problems buried in your premise, take a look at the Great Screenwriting Class. Techniques for writing the detective story, including all the unique story beats, are found in the Detective, Crime and Thriller Class and the Detective Genre Software.
