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It's kind of like has such an interesting concept that it's worth a watch just for the story.
Jack Black plays Hal Larson, a shallow guy who chases after beautiful women just for their looks.
In reality, she is morbidly obese, and everyone can see it except Hal.
That means that we have Gwyneth Paltrow alternating between looking like Gwyneth Paltrow and wearing a fat suit and prosthetic makeup.
Olyphant and Kevin Smith play two of those friends. Mc Gregor plays Catcher Block, a playboy journalist who goes undercover to try to get her to fall in love with him, undermining everything she wrote in her book. The story takes place in the flashy world of magazine journalism in 1962 New York City.
Also, please note Amanda Peet's very bad punk rock hair when the characters first meet.