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Macdonald plays Kate, who just recently moved to Chicago to 'start a new life,' 'make a fresh start,' or any other cliché you choose to apply. She was formerly married to a guy involved with some shady people who stood ominously around her front door, and who presumably gave her the black eye she sports as the film opens. Kate is one of those characters so fraught with emotion that she has to go sit in the middle of a garish, empty Catholic church to demonstrate her spiritual turmoil.
Kate meets Frank Logan (Keaton), a tortured contract killer, through some sort of strained coincidence by which she mistakes a staked-out Logan for a suicidal man (don't ask). In so doing, she kinda sorta bears witness to Logan's covert operation, which piques the interest of a jolly detective (Tom Bastounes) who becomes suspicious of Logan and amorous of Kate. This sets up an awkward love triangle the movie will try, and fail, to legitimize for the duration of the story, if for no other reason than the film is incapable of establishing any real connections between its characters. The detective clearly wants Kate, and she is clearly repulsed by him, which leaves the stoic Logan as a mysteriously attractive force. Clearly, the film intends for us to feel the palpable connection between Kate and Logan, but the laborious hitman plot delays their connection to such a degree that they barely share any scenes before it's time for the Big Finale.
Keaton makes his directorial debut with this film, and like many actors' first features, Gentleman's visual storytelling is a bit heavy-handed, with an over-reliance on over-emotive close-ups and a few too many choppy edits. In all honesty, though, the visual element is not key to this film's demise. Nor is the acting; Keaton has always possessed one of Hollywood's most interesting screen personas, and he adds intriguing spice here. Macdonald is also good, even if she's doing a variation on the do-gooder she almost always plays.
The Merry Gentleman's central flaw is its script, which is an uneasy clash of pleasant character study, cutesy human comedy, insipid woman-in-crisis story, and hard-boiled hit-man tale. The quiet emotional connection between MacDonald and Keaton works, but the dangerous intrigue cumbersomely takes up so much time that when the romance hits an emotional high and Kate tells Logan, 'you are the sweetest man I've ever met,' it literally means nothing to us. The strange subplot involving the smitten cop exists as nothing other than awkward plot filler, until the movie brings the detective back at the end to participate in a gumshoe climax that makes no sense for the story or the characters.
What's so depressing about The Merry Gentleman is that it came from Keaton, who exudes such intelligence on screen that it's surprising it didn't seep into his work behind the camera. His work as a first-time filmmaker is not so much a failure as a surrender, allowing Ron Lazzeretti's disastrously confused script to play out without much additional tweaking. The result is a film lost in a boondoggle of hazy plot mechanics.
The DVD includes a making-of featurette.
God bless ye.
