Hired killer Frank Logan (Keaton) hates himself and wants to die. We catch this tidbit pretty early on as after each hit, Frank starts to commit suicide but pulls himself back from the edge at the last second. During another day at the office, Logan spies a pretty, angelic figure in the window adjacent to his mark and nearly blows his hit. Yet he pulls through and pops his target and then contemplates jumping off the roof he’s on. That is until the angel figure on the window spies him, screams and inadvertently foils the suicide attempt.
From there Logan seeks out this saving grace, a recently single Scottish girl named Katie (Macdonald) and a sort of friendship is struck up. Katie has secrets of her own as she has recently left an abusive relationship and is trying to find her way in the big city of Chicago while keeping her past a secret. “The Merry Gentleman” is clearly supposed to be a character study however the solemn tone and overall quietness of the film do nothing to establish characters and that makes getting to know the people up onscreen rather difficult.
Following the assassination from the rooftop, a couple of local cops interview Katie and one of them (Bastounes) takes more than a professional interest in her. Funnily enough, we end up knowing more about the “recently divorced, chain smoking, alcoholic” cop than the other two main characters in the film. And the more we get to know him, the more annoying and stalkerish he becomes. I should add that this film features an outstanding, adorable and quite sad performance by Macdonald as Katie, possibly the most naïve woman on planet earth. She gets picked up on no less than 5 times in the film and each time doesn’t figure out that she’s being picked up on until her only recourse is shooting down guys at the last moment. Again, Macdonald is fetching and her using her true Scottish accent is cute, but it’s just hard to believe someone this sheltered and gullible can live in a big city and not get trampled.
Although I’m always game for anything with Michael Keaton, this film just feels uneven and struggles with what it’s trying to say. Tempo is also a problem as the film is super slow. I’m not against slow films and I did enjoy seeing Keaton’s character grow somewhat in the film, but it’s a tough haul when there’s lots of silent long shots and no real build up or resolution.