The Merry Gentleman is the story of Kate, a young woman who flees her abusive policeman husband, moving to Chicago. In her new life, she befriends a co-worker but otherwise generally keeps to herself, due to her embarrassment over a black eye left over from her husband's latest attack. Most everyone she encounters is of low character, which reinforces her feelings of loneliness and reclusion.
One night, she is seen in an office window through the rifle scope of professional hit man Frank Logan, who is on the roof of the opposite building, as he prepares to shoot the occupant on another floor. Afterwards, rather than leaving, he removes his hat and steps out on to the ledge as he apparently prepares to jump. As Kate steps out onto the sidewalk, she looks up at the falling snow and sees Frank on the ledge. She cries out, startling him into safely falling backward onto the roof.
She decides to bring a small bit of joy to her life by buying a Christmas tree. Later that night, she encounters Frank at her apartment building. She doesn't recognize him as the man on the roof, and he helps her carry the big Christmas tree to her apartment. He later returns to meet with her, but collapses from pneumonia before he can reveal why he's there. Kate rushes him to the hospital, and despite the awkwardness of their conversation there, they develop a friendship that has hints of romance. Some time after his release, she mentions the old hat that he wears and wonders about "the things it has seen," unknowingly referring to the many men that Frank has murdered. Meanwhile, Kate also becomes the romantic interest of Murcheson, the detective investigating Frank's latest murder. Murcheson asks Kate out to dinner, but she mistakes the date for a meeting about the investigation, and cuts the date short when she realizes Murcheson's romantic interest.
Initially, the police remain oblivious to the fact that Frank is a professional killer, due to his framing the murder on another man, who he then killed in a manner to make the police suspect suicide. However, complications arrive when Kate's husband, Det. Michael Elkhart, tracks her down and breaks into her apartment. Michael swears he has become a safe and spiritual man, but the encounter leaves Kate badly shaken. She turns to Murcheson for help, but before he can intervene, Frank fatally shoots Michael in his motel room and makes it look like a suicide. The police begin to suspect that Frank may be behind all three deaths.
Murcheson asks Kate out on a second date, which she reluctantly accepts. The date turns horribly awkward, however, when he reveals that he suspects Frank to be a killer. Feeling guilty about her dead husband and disturbed by Murcheson's suspicions, she visits a church. Frank finds her there, but she is not comforted by his promise never to hurt her. Frank leaves the church and quietly walks out of her life, choosing not to subject her to the fear of knowing a professional killer.
The exact details of Frank's departure remain ambiguous. Apparently considering suicide, he drives to a high bridge over a forest and tosses his hat into the river far below. Then another car arrives and a man comes out. We later see Frank retrieve his hat from the water. Unsatisfied with his dreary day job as a tailor, having left behind the only pleasant aspect of his life, and placing the familiar symbol of his sinister side back on his head, he walks off into the woods.Frank Logan: Michael Keaton
Kate Frazier: Kelly Macdonald
Murcheson: Tom Bastounes
Michael: Bobby Cannavale
Diane: Darlene Hunt
Goldman: Guy van Swearingen
Mr. Weiss: William Dick
The film was presented at the 2008 Sundance Film Festival, and was well received. A review from the festival stated:
"The Merry Gentleman is slow paced . . that's an attribute. Keaton doesn't rush anything in his story . . It is a glowingly photographed, impeccably performed magical realist drama . ."
The movie was released on May 1, 2009 to positive reviews (noting Keaton's crafted directing of the film and MacDonald's performance), with a 'fresh' 67% rating from 73 critics at Rotten Tomatoes. Lisa Schwarzbaum of Entertainment Weekly wrote of the film, "This Debbie Downer of a drama is a bitter slug".