It would be one thing if Cherry was simply a listless, ill-conceived star vehicle designed to show us that a Hollywood star has more thespian chops than we realize — a forgettable misfire along the lines of Ashley Judd's Helen, Sandra Bullock's 28 Days or Bill Murray's The Razor's Edge. But Cherry leaps off the screen at you every chance it gets, with the kind of swagger and self-assuredness that usually signifies a film that has the goods. It's like watching somebody strut into a room thinking he owns it, oblivious to the toilet paper hanging off his shoe.
The brothers Russo certainly never let you forget that they are behind the camera, employing all sorts of complicated shots, jazzy titles, breaking of the fourth wall and other attention-grabbing techniques. In addition to their resistance towards giving the main character a name, other characters have names like "Pills & Coke" or "Black" (an ominous man barely glimpsed, whose face seems to be covered in some mixture of tattoos and facial hair). At one point, Holland seeks help from an uncaring physician (Thomas Lennon) whose desk placard reads "Dr. Whomever"; the banks he robs to support his habit have names that riff off well-known institutions (Capitalist One, S***ty Bank, etc); this all feels like some kind of ripoff of films like Repo Man and Natural Born Killers, stripped of any commentary beyond the cheap joke of a subversive logo.
So what is Cherry trying to say exactly? It's hard to tell beyond "life sucks," but there sure are some divine moments of directorial inspiration that could have yielded meaty moments if given the chance for fuller exploration. During basic training, Holland's character says that he feels like they're all children playing grown up — and we see them transform into children wearing oversized military uniforms. Another brief shot has soldiers dancing in a Busby Berkeley-esque overhead formation.
Everything is touched upon so briefly, the next topic moved to so breathlessly, that it's a reminder of that old axiom: Jack of all trades, master of none. If you want to watch a great film about the madness of the battlefield, watch Full Metal Jacket or Jarhead or Three Kings or The Big Red One or Saving Private Ryan or a dozen other better movies. If you want to dive into the mind of a junkie, watch Requiem for a Dream or Trainspotting or Bug or Naked Lunch. If you long for doomed lovers, reach for Sid & Nancy, Blue Valentine. Want a better movie about bank robbing? That would be, literally, any movie ever made about bank robbing.