Forty years ago, the idea that Rowdy Yates from TV’s Rawhide would turn out to be a talented director would have seemed ridiculous. Yet it came to pass, with Clint Eastwood proving to be one of Hollywood’s most celebrated filmmakers. In addition, he’s also one of its most prolific, churning out an average of one film almost every year over the past decade. But in spite of making such well-regarded films as Unforgiven, Mystic River, and Million Dollar Baby, the truth is that when a filmmaker works at such a rate, there are bound to be some clunkers in the bunch. Surely enough, Eastwood had his share of mediocre or even subpar films throughout his career, even in the fertile period of the nineties. In the case of movies like True Crime and Blood Work, the middling quality of the films wasn’t too big a deal, as they were disposable adaptations of forgettable airport novels.
Then there was Midnight in the Garden of Good and Evil. A far cry from the likes of Absolute Power, Midnight was based on an honest-to-goodness acclaimed work of literature. John Berendt’s book, based on an actual Savannah, GA murder case, was a publishing phenomenon, residing on the New York Times bestseller list a full four years. For the first time since his Academy Award-winning Unforgiven, Eastwood was making an honest-to-goodness prestige project, and he devoted all his attention to directing the film, handing over the acting duties to the likes of Kevin Spacey and John Cusack. Anticipation was high, especially among fans of the novel who were curious to see how Eastwood would translate it to the screen.
Trouble is, like many really good books, Midnight in the Garden of Good and Evil doesn’t exactly lend itself to being adapted. While most good adaptations are inspired by books with strong, tight stories, much of the appeal of Berendt’s book is anecdotal, with plenty of fascinating characters orbiting around the story’s center, the trial of Jim Williams. Unfortunately, Eastwood is generally at his best when working with a relatively straightforward plot, and consequently, his attempts to mix the court case with the incidental dramas in Savannah just don’t quite work. It doesn’t help that Eastwood never really allows Savannah to become a natural element of the story like it ought to be. Watching his more successful adaptation of Mystic River, it’s hard to imagine the story taking place anywhere else, but I almost never got that vibe from 
Midnight, in which the city feels more like a backdrop than an actual setting.
Part of the problem is that Eastwood shies away from one of the book’s most important themes- the hypocrisy of Savannah’s upper-class when confronted by Williams’ homosexuality. Berendt’s novel addresses the almost tangible sense of abandonment that Williams felt when his “friends” refused to testify on his behalf once word of his sexual predilections came to light. But while it’s mentioned in passing in the film, Eastwood makes far too little of which should be a central issue. Without this undercurrent, the trial loses most of its energy, becoming little more than a mediocre courtroom drama with a few mild twists.
Also disappointing is the film’s treatment of the friendship between protagonist John Kelso, a Berendt surrogate played by John Cusack, and the story’s most famous supporting player, The Lady Chablis, who plays herself. In both the book and the film, the two characters- one a straitlaced northerner, the other a local transsexual- get to know each other as the story progresses, and while it’s pretty clear that nothing sexual ever transpires between them, there’s a tantalizing ambiguity about Chablis’ 
feelings toward Kelso. Sadly, Eastwood and screenwriter John Lee Hancock seem skittish about the possibility that audience members might think their hero is gay, so they concoct him a love interest who wasn't in the book, played by Eastwood’s daughter Alison. The romantic subplot is a complete waste of time, never advancing the story or working in any other way other than to reassure the audience that John Kelso is all about the ladies.
That said, both Cusack and The Lady Chablis are actually quite good in the movie. Cusack plays his usual charming, brainy type, but then, the story needs a levelheaded character in the middle of the eccentric locals. And The Lady Chablis is pretty priceless, especially when she’s playing off Cusack- I can’t imagine a more established actor playing the role even half as convincingly, no doubt because she’d already been playing the role for years even before the book, let alone the movie. And most of the rest of the cast is also fine- Spacey is courtly but subtly menacing in one of finest performances, and Jack Thompson has fun as Spacey’s defense attorney, a local hero (he’s the owner of the University of Georgia’s mascot “Uga”) who’s surprisingly neither a blowhard nor an over-the-top rube. The weak links are Alison Eastwood (who to her credit has almost nothing to do) and Jude Law as the murder victim, who when we see him in flashbacks is too mannered by half.
More than most filmmakers working today, Eastwood works in the classic tradition, allowing the film’s story to dictate his directorial decisions. Unfortunately, it never feels like he got a handle on the story. The courtroom scenes have no momentum, there’s too much gratuitous material involving Alison Eastwood’s character, and the local color just doesn’t work like it does on the page. After all, it’s one thing to imagine a guy walking a nonexistent dog or tethering flies to his clothing, and another 
entirely to actually see them. And late in the game, Eastwood abandons his low-key and realistic style to inject some magical realism into the film, but the moment doesn’t work because it feels so out of place with his style.
In the end, one gets the sense that Eastwood’s brand of filmmaking just didn’t mesh with Berendt’s story. Perhaps someone like Robert Altman could have pulled it off, given his gifts with ensemble casts and Southern settings, or even the documentarian Ross McElwee, chronicler of the Deep South in films like Sherman’s March and Bright Leaves. I might have suggested Errol Morris, considering his ability to portray eccentrics without condescending to them, but then, Morris' previous fiction feature didn’t turn out so well, did it?