"Forest Whitaker now = good. Forest Whitaker then = not so good."
A hitman by the name of Dekker (Forest Whitaker) is sent on what will be his final job, but every step of the way something just feels wrong about it. First he’s asked to meet the client, something he never usually does. Then the client turns out to be an asshole, which doesn’t leave our hero confident about the job. Those feelings are then multiplied when the client lays out the targets of the hit… his girlfriend (Sherilyn Fenn) and child. “It’s a crack baby, you’d be doing it a favor!” he exclaims. We’re supposed to be shocked at this, but it comes off a little too comical for real effect, like much of the film.Based on the play Insider’s Price by Kenneth Pressman, Diary of a Hitman follows Dekker as he tries to bring himself to make an animal of himself. If he opts not to fulfill the job, his boss (Seymour Cassel) tells him, he’ll be pissing off some very scary folks. For the rest of the running time we basically watch Whitaker gearing up for and talking about the task at hand, generally in a way that is supposed to see us feel like he’s an enigma, but the dialogue fails to find the spark that could pull such a thing off.
Excessively self-aware and not entirely finding a point to hang its story on, Diary of a Hitman was directed by occasional director, occasional writer, most of the time acting coach Roy London, so it’s not surprising that a lot of time is given to the actors to prove their mettle. Sherilyn Fenn in particular shows that she’s far more talented than her roles allow her to be, but Whitaker doesn’t grab the ball she’s passing him, let alone run with it. It was early in his career and he was only three years past playing a small part in Jean Claude Van Damme’s Blood Sport, so maybe this was just part of his progression and education in the acting field, but whatever the reason it’s just not going to light up Forest fans.A little too much Lifetime and not enough Showtime, Diary of a Hitman doesn’t stink, but it won’t exactly be a film you can’t look away from. Wait for a cable showing.