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Cupidity (2004)
8/10
Entirely entertaining
18 May 2004
The New York International Independent Film and Video Festival closed with the very funny and entertaining "Cupidity", a new film by director John Gallagher ("Blue Moon", "The Deli"). The docucomedy is based on improv revolving around James, the lead character, and his journey into the fiery pits of dating hell in an attempt to find true love.

After being dumped by his girlfriend Bethany, James goes on an odyssey of 20 dates, all seeming to come out of a fun house of incompatibility. Each date serves as its own comedic set piece in which James is confronted with a wide variety of women who present him with roadblocks in his quest to find Miss Right.

The film is wall to wall with talented new faces, who are exactly the type you would hope the festival would shine its light on. The brightest of these future stars is the lead, James Gilmartin, who has tremendously appealing charisma, personality, and comic timing as he carries us through the film date after date. He has a strong leading man sensibility, and is a consistent point of reference as we see him matched with swarms of wrong women. Gilmartin demonstrates a true understanding of what an actor must bring to the role of the male lead in a romantic comedy: a man who has a personal sense of dignity and charm, while having the ability to laugh at himself. His performance makes us feel sorry for the poor guy, while at the same time leaving little question that he's of a strong enough personal character to find his way through the loneliest moments of doubt; enabling us to feel secure that this guy's going to be okay, and stronger than before. Someone to laugh with, not at, we are drawn in to James, and are thoroughly entertained for the entire ride.

The actresses who play his 20 dates also deserve much praise for their ability to individually create interesting characters who, one after the other, simultaneously offer James different and bizarre obstacles to finding the right woman; and each give the audience something fresh, interesting, and funny to watch. The film could have chosen to cover a little less of the entire dating spectrum than it did, allowing for a deeper narrative thread between the main couple's breakup, journey, and resolution. But that said, Gallagher has non the less presented a funny, entertaining, and successful experiment in romantic comedy that deserves the attention of audiences everywhere who are looking for love, laughs, and something to soothe the soul.
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