Portrait of the asshole as a young man
Tony Montana, Mark Brian Smith
Troy Duffy
The Setup: 
Boston bloke get a film directing gig and record label. Then it vanishes. He's an asshole to everyone throughout.

Overnight tells the story of Troy Duffy, a guy from Boston who wrote a script called The Boondock Saints, sold it to Miramax, got a deal to direct [with final cut] the movie himself, got a record deal for his band, and pissed it all away. And the movie establishes pretty directly that the reason these projects failed is because Duffy is such a class-A loser asshole.

How many of us [myself definitely included] have ever created that song/screenplay/novel/artwork/bad movie website and been completely sure that it was a work of untold genius that the unwashed hordes may not in fact be ready for, but will surely blow their minds, and they will all fall down and proclaim our genius? Then you actually show it to someone else, and start getting those "Well, I liked it, but did the moose have to step on the frog?"-type comments, and your satisfaction suddenly turns to rage and angry withdrawal, because the morons do not understand the perfection of your creation. In fact, it is perfect precisely BECAUSE it exists free of outside influence. And you realize [or do not realize] that that blissful period of creative satisfaction could only exist in a vacuum, before your work is held up to any kind of review, and once it has been tainted in such a way, it's kind of ruined, and you lose a great deal of interest in it. You also realize, at the same time, that it will never be published/displayed/whatever without anyone else seeing it, and so you retreat back to your cave, defeated.

Thoughts of that nature [run amok, in this case] are what this movie made me think about, as well as the variety of conceptions people have about their own abilities, and about Hollywood. When the movie deal is concluded [at the point where the only tangible evidence of Duffy's creativity is his script], Duffy buys into the generic concept that these morons in Hollywood need to be shaken out of their dream worlds by the "real" voice of the blue-collar schlub, and him and his script is just so raw and utterly beautiful that it is JUST the thing to do it. He is constantly interpreting the behavior of the Hollywood people he meets as being shaken to the core by his raw authenticity. He talks about how he attends meetings with people in suits, and he comes in unkempt and hung over, in overalls, and blows them all away with how blindingly brilliant he is, and how he alone, who has no Hollywood experience until now, understands the true nature of Hollywood. He sneeringly dismisses the work of Keanu Reeves, Ethan Hawke, and Jerry Bruckheimer. My particular favorite is, after being turned away at the door of Maverick records [where he thought he had a record contract] he decides that this must mean the Maverick execs are "scared shitless" and "holding emergency meetings" because of the threat Duffy represents. On the other side, it's also interesting to see stars like Mark Whalberg expressing the complementary idea that Hollywood is out of ideas and we need a more "real" voice from the outside to shake things up. It's delusions all round, and the rest of the film chronicles them being systematically torn down.

First the Boondock Saints goes into turnaround. This isn't handled directly, but the calls from Miramax slow to a trickle, then stop. Duffy, sure that he is the hottest thing and that everyone wants a piece of what is obviously pure magic, only grows more belligerent, assuming that if this one falls through, another deal is just around the corner. It isn't. Then his record label drops the band. At this point Duffy's nearest targets are his friends and bandmates, and he turns his force on them. He won't let them direct any part of their own future, blames then when things go wrong, and takes the credit-and I mean ALL the credit-when things go well.

The other subtext here-the first being the aforementioned study of various delusions about creativity and Hollywood-is the story of Duffy's friends and band managers Tony Montana and Mark Brian Smith. They are also the directors of this movie. They agreed to make a documentary charting Duffy's rise to fame, and you can sense at a certain point that they decided to change their project into a document of his monumental assholishness. This moment may have been when they found out that the band, which they were co-managers of, had signed to Atlantic without their knowledge, and Duffy refused to give them any money for the work they had done on his behalf until that point.

This movie also makes a fantastic anti-smoking commercial, as they are all smoking so much--in virtually every shot--that it kind of becomes nauseating and pathetic after a while.

Anyway, things go from bad to worse, and near the end, after everything's gone bust, Duffy's brother [and band member] stages an intervention to try to talk some sense into Duffy. He is met with a sound "Fuck You." Soon after this the band is shown having their pictures taken for the album cover. I found it kind of funny that for all the big talk about how great they were and how, in one record exec's words "It's either going to fill arenas or go over people's heads" [i.e. it couldn't just be that it SUCKS], the pictures they take are the utterly generic stand-against-a-desert-backdrop-wearing-sunglesses-with-a-three-days-beard-and-leather-jackets garbage that all but announces "this band sounds pretty much like any other." One is gratified to find out that the album sold 690 copies during its first six months, but I do feel bad for the other guys. Though, of course, if it had done better, they'd still be stuck with Duffy.

Incidentally, a good condition used version of the CD is currently retailing for $30 on Half.com.

By the end, the movie's a bust, Duffy's film career is finished, his music career is finished, and the film shows his bandmates working in construction, supermarkets, as bartenders, etc. One feels bad for the band, but not for Duffy, who has drained any possible sympathy by making himself such a royal asshole, and pissing away an opportunity any of us would kill for.

Should you watch it: 

Yes. Even though I've essentially told you the entire story, the nuances and the portrait of delusion still makes it worth watching.