Written and directed by Estevez, the film follows the aforementioned twenty two people throughout the day leading to the assassination of the Senator. Most are employees of the famed Ambassador Hotel, some are guests. In order for the film to work, we have to have an idea of what makes a majority of these characters tick. Clearly, with this many people, this sort of thing has to happen quickly and make an impact. Also, the characters have to have a connection to the story or the idea of the film. Estevez, whose previous credits as a director include "Men at Work”, starring Estevez and his brother, Charlie Sheen, as garbage-men in a wacky adventure, is working on a larger canvas here and he doesn’t seem able to control it. Some of the characters are interesting and we learn a little about them, others are mere names and actors playing them. Some of these characters have a connection to the main story, others don’t. When you have this many characters, everything has to fit, like the pieces in a jigsaw puzzle or we begin to wonder why we are wasting any time with them.
Martin Sheen, Emilio's dad, plays a well-to-do guest at the hotel whose wife (Helen Hunt) has forgotten her good shoes. Ashton Kutcher plays a drugged out hippie who leads two of Kennedy's campaign workers on an LSD trip. Heather Graham plays a switchboard operator at the Ambassador who is having an affair with the hotel manager. Harry Belafonte plays a retired man who hangs around the hotel lobby. At one point, he disappears for a nap. I felt like joining him.
Clearly, many of these actors wanted to be involved in the film to be involved in the film. They simply aren’t on screen long enough to make an impact or advance their careers. I suspect many felt the message of this film was worth telling. More on that later.
Then, there are a number of promising characters who don't really work. Nick Cannon plays a Kennedy Campaign worker who is talked up for a Secretary position. But rather than develop his character, he stops and delivers a monologue about the poll conditions in Watts. A more experienced actor may have been able to make the role seem more natural, less high school play. Estevez plays the emotionally abused husband of a fading, alcoholic singer. In each of his scenes, he has a blank expression plastered on his face. He must be thinking about all of those actors on his payroll. Laurence Fishburne plays a sous chef at the hotel. His main contribution to the story is an extended discussion with some of the Latino kitchen help, to discuss how he gets ahead in this unfair world.
Then, there are a handful of people who are either interesting, connect to the story or both.
William H. Macy plays the manager of the Ambassador Hotel. Throughout the day, he has to deal with a false fire alarm, various personnel issues, his wife (Sharon Stone) who works as the hairdresser in the hotel's salon and his new mistress, a switchboard operator played by Heather Graham. Anthony Hopkins plays a retired doorman at the Ambassador, trying to stay alive by hanging around the lobby, interacting with the employees and guests he has known his entire life. Hopkins' role doesn't seem to have a lot to do with the story, but let's face it, watching Hopkins read the phone book would be interesting; he always imbues his characters with so much history and personality. Sharon Stone plays the hairdresser at the hotel and interacts with a young bride (Lindsay Lohan) and the boozing singer (Demi Moore). Her character has a world weariness to her and she has a couple of interesting conversations, making her believable and watch-able. She explains to Lohan why she got married. "He was the most handsome man in the world." William H. Macy? He has charm, but the most handsome man in the world? And then there is Demi Moore who does a surprisingly good job of playing the fading chanteuse. She is not a likable character and is all the more convincing because she is so unlikable throughout.
In more experienced hands, all of these characters (and the many I didn't even mention; Elijah Wood's soon to be drafted groom, Shia LeBeouf's drugged out campaign worker, Freddy Rodriguez’s Dodgers fanatic busboy, would have a connection to the story, work together like the pieces of a puzzle. In Estevez's hands, many don't seem to have any connection to the main story, that of Kennedy's assassination.
Because so many name actors appear in the film, I suspect many appeared for scale, simply because they wanted to be part of the story, part of the message. But what exactly is that message? Many of the monologues are intended to give a feeling of what life was like in that era. This would lead to Robert Kennedy. The filmmaker wants us to feel that Bobby would have fixed all of the problems we were having. I firmly believe this as well, but the filmmaker does not get the message across. He doesn't connect the dots. If someone has an exchange about something, we should also see part of this. Why can't we see footage of what is happening in Watts? Then hear Cannon's character discuss it? It would be much more compelling.
Ultimately, because the characters don't make a lasting impact (i can't even remember most of their names) and the message is not artistically or convincingly portrayed, the film is a mess.
"Bobby" is a noble effort, but Estevez doesn't have the skill or the talent to pull off such a thing. He gets credit for trying, but that's about it.