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.