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I'm surprised no one has suggested the critical and commercial Gweneth Paltrow Rom Com View from the Top. It had a lot of potential and a great comedic cast (Mike Meyers, Candice Bergan, and Christina Applegate but it never really gelled together into any kind of remotely good film. It includes my favorite terrible rom-com trope "Woman achieves her dreams and realizes there worthless without a man". Also featuring Gweneth Paltrow's cup size go up and down between scenes depending on what costume they put her in.