It was somewhat entertaining and some parts were funny, but it was mostly cringey. The problem I have with the movie is that Hal, being shallow, only sees beauty as skin-deep, until he is hypnotized. Then, he begins to see an obese woman, who is kind and good-hearted, as skinny. BUT HE IS STILL SHALLOW!!! That didn't change,
because he still has no idea she is obese! This first of all implies that only skinny women are actually pretty. What would have been better was if Hal still saw the obese woman as she was on the outside, but began noticing and caring for her heart and character instead, while she remained looking the same physically. Maybe that would have made a less entertaining movie and someone else other than Gwyneth could have played the part, but it would have been a better moral to the story - and the movie was a flop anyway, so no big loss!
Another issue I had was that Gwyneth's character was actually way too good for Hal. He was an a**hole and she was kind and good-hearted, deserving a much better, higher-value man than Shallow Hal. I couldn't even understand why she would be attracted to him.