Woody Allen is a pretty inconsistent filmmaker. While last year's Midnight in Paris deserved all the praise that it got and more, the 2010 film You Will Meet a Tall Dark Stranger was a real disappointment. His entire career is spotted with truly great work intermingled with mediocrity. With To Rome with Love, he provides both in the same film.
In the style of New York, I Love You and Paris, Je T'aime, To Rome With Love tells a collection of stories that are largely unrelated except that they take place in the same city. Those stories include:
Hayley (Alison Pill), an American student studying abroad, falls in love with and gets engaged to Michelangelo (Flavio Parenti). Her parents, Jerry and Phyllis (Woody Allen and Judy Davis) are coming to meet Michelangelo and his parents.
Antonio and Milly are newlyweds on their honeymoon. Milly goes out for a walk by herself and gets lost, while Antonio has to pretend that a prostitute (Anna, played by Penélope Cruz) is his new wife.
Jack (Jesse Eisenberg) is an architecture student living with his girlfriend Sally (Greta Gerwig). When Jack meets all-star architect Jerry (Alec Baldwin), Jerry spends all his time trying to make Jack fall for Sally's best friend Monica (Ellen Page).
Leopoldo (Roberto Benigni) is a completely ordinary man with a normal office job who suddenly finds himself the most popular man in Rome. The public can't seem to get enough of even the most mundane aspects of his life.
The stories aren't really connected, but they're told in an intertwined manner that allows us to stay involved with all the characters for the duration of the film. This is an interesting approach, but it seems to backfire because while each of them starts strong and maintains that plateau for most of its duration, each also has a weak ending. As a result, the first eighty minutes of the movie is the kind of charming perfection we get for all of Midnight in Paris, but it almost immediately transforms into something lackluster and clumsy as it begins to tie up loose ends and finish up those stories. Had the stories been told serially rather than in parallel, then the moments of tedium would have been shorter and the film immediately revitalized by the start of the next. On the other hand, if they'd managed to come up with a decent ending to even one of the stories, then the whole thing could have also been saved.
It's not fair to imply that To Rome with Love is a bad film, because that's far from the truth. When it's hitting on all cylinders, it's on par with some of the best of Allen's films, and when it begins to flounder it never becomes bad but rather just stops being good. In the beginning, it's easy to overlook minor flaws (like a very stuttery 360-degree sweeping shot when Milly begins to realize she doesn't know where she is), and there seem to be fewer technical missteps near the end when they would be more easily noticed. It's really the hope of what could have been rather than any specific shortcoming that leave you with a soured impression.