9. Manhattan (1979)
The terribleness of this film is more than debatable: It sits with a comfortably "fresh" rating of 98% on Rotten Tomatoes, Roger Ebert awarded it 3.5/4 stars, and I myself - a longtime fan of Woody Allen's - enjoy the movie immensely. So why include it on the list? For starters, the director himself thinks it's terrible. After it was completed, Allen asked United Artists not to release it, offering instead to make a movie for free. In Woody Allen: A Documentary, he recalls thinking to himself, "At this point in my life, if this is the best I can do, they shouldn't give me money to make movies." The other reason is that despite how beautiful New York City looks in black & white with the 2.35:1 aspect ratio and the often hilarious dialogue, this movie is ripe with Romantic Comedy cliche. This may be because Woody Allen himself reinvented the Romantic Comedy just two years earlier with Annie Hall, arguably paving the way for the next forty years of "guy meets girl" movies. They're all here: A twice divorced leading man (Allen, obviously) whose ex-wife is writing a confessional about their marriage. Since their divorce, she has come out of the closet, is now living her new partner, and has custody over their son. His best friend is going through a tough time in his marriage and has begun seeing another woman named Mary (Allen regular Diane Keaton). Classically, the relationship between Allen and Mary begins with distaste before blossoming into a romance. The romantic entanglement creates the familiar love-triangle as two best friends fight over the same woman. Add to the mix Tracy, the 17-year-old high school student Allen's protagonist is seeing at the beginning of the film. He constantly reminds her she can't get too serious because of their difference in age and urges her to go to London and study acting. When things become serious with Mary, breaks it off much to her dismay. After all of his relationships fall apart, he has the cliche realization that what he was looking for had been right in front of him the whole time: Tracy. The movie ends with Allen running out of his apartment, through the streets of New York in a cliche last-minute-sprint. Predictably, he arrives at the lobby of Tracy's apartment just as she's about to leave for London and confesses his love for hear by asking her to stay behind. Is it predictable? Certainly. Is it worth 96 minutes of your time? Without a doubt.