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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.

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This movie is insanely bad, but features really great actors failing marvelously. Like slowing down past a car wreck I want to watch this on repeat to find out how this was made.

 

Accurate tag lines for the movie: Like Miss Congeniality in reverse, you slowly hate every character more and more. Paltrow in her least convincing role yet: trailer trash... Featuring a cameo by Mike Myers to add the final nail in his coffin.

 

If you like boobs, bad makeup, bad hair, and an exhausting rags to riches (but not really rich because she is still just feeding jerks drinks all day) you'll love this movie!

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 So funny that garbage like this was what Ruffalo was up to before he got cast as the Hulk. I also felt bad for Mike Myers, seemed to be trying really hard for what amounted to probably 5 min worth of screentime. 

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