So much has been said about Sullivan's Travels that I don't see too much use in simply talking about how good it is. On top of that, since one of its chief aims is to suggest the vitality of simply enjoying something that's light and funny, especially amidst the turbulence of real life, I feel that maybe it's best just to sit back and enjoy this one. After all, what the film suggests about making movies is precisely what the film is itself. John Sullivan goes from wanting to make serious, socially conscious motion pictures to realizing that the greatest virtue a movie can have is to incite laughter. The film, likewise, feels like Preston Sturges' grand statement about his own purpose in making movies. Let's not forget that he first achieved success by writing serious material for films like The Power and the Glory (arguably a precursor to Citizen Kane), and Diamond Joe.
So I won't go into any great detail about why Sullivan's Travels is so good because the only way to understand what it's trying to do is to watch it.
But there are two quick points I want to make about it that came to my attention when I re-watched it recently. The first is that this a comedy that's partly about what happens when you disguise yourself into something that you're not. Now this is a common trope among comedies, from Barbara Stanwyck pretending to be an English socialite in Sturges' own The Lady Eve, to Melanie Griffith faking it as a business executive in Working Girl. What makes Sullivan's Travels stand out though amidst this comedy tendency is that usually the disguise involves someone attempting to enhance their status. In Sullivan's Travels, though, it involves Sullivan diminishing it, going from wealthy Hollywood director to bum in order to gain life experience. There are two problems here: the first is that this would work if it were an end in itself, but for Sullivan, the end is to enable him to create his socially realistic movie, under the mantra make what you know. As a result, he always has an out, the ability to simply jump a train (or in this case, a bus from Hollywood that follows him around to report on his journey and make sure he's okay) and go back to his lavish Hollywood home. This makes his entire venture seem every bit as artificial as it is. And I realized that it's easier to pretend to be someone higher up than you really are than to be try to be someone lower. It's also funnier. While there are some humorous moments, like when Sullivan is trying to be a bum, like a train scene where he's clearly an amateur among a couple seasoned pros, most of his encounters with the homeless play out awkwardly because, well, that's how it would be in real life I suppose.
The second problem is that to really gain this sort of experience--to not just mingle with the lowest of the low but to be a part of it--will only really occur out of circumstance. It's circumstance that makes the real bums in Sullivan's Travels, not choice. Sturges realizes this, and the film really becomes a work of genius to me when circumstance turns Sullivan into not just a bum, but a prisoner sentenced to 6 years in a labor camp. It takes circumstance, in this case a bum who robs Sullivan before being killed by a train, after which he's mistaken for Sullivan because of the identifying shoes he stole.
Because he's considered dead and confined to a prison, Sullivan has no way to reach out to his Hollywood friends, and thus what was a game becomes an entirely real situation.
The other point I wanted to make was that at this point, the film, which had been a perfect example of Sturges at his funniest, becomes an actual drama, dark and even a little disturbing in the way Sullivan's innocence is rendered completely useless because of the nature of his circumstance. The music grows more ominous, the images cloaked in the kind of heavy shadows you'd find in a crime picture.
The realism Sturges is able to create is the kind Sullivan wants as well, and his sudden arrival into legitimate bleakness is exactly what he needs to make his film. The big irony of course is that it's only through this experience that Sullivan is able to reach his epiphany when he and his fellow prisoners get to attend to a Disney cartoon, the laughter it ignites in them serving as an antidote for their miserable lives.