Of course, it's not a stretch to say Shallow Hal wasn't the most politically correct movie ever made, especially by 2020 standards.
Here's the synopsis:
The story revolves around Hal (Jack Black) who, taking his dying father's advice, dates only the embodiments of female physical perfection. But that all changes after Hal has an unexpected run-in with self-help guru Tony Robbins. Intrigued by Hal's shallowness, Robbins hypnotizes him into seeing the beauty that exists even in the least physically appealing women.
As her svelte self and in a fat suit, Paltrow played Black's love interest Rose. The fat suit represented the real-world morbidly obese character, and Paltrow as she actually looks was the version only Black could see.
Paltrow and Keating were taking what Netflix calls "The BFF Test." Keating was asked to guess Paltrow's least favorite role. He apparently nailed it when he said Shallow Hal.
"Exactly," said Paltrow.
Keating said he wasn't sure who advised her to do the movie, but it wasn't him, as he didn't work for her then.
"That was before your time," Paltrow said. “See what happened? Disaster.”
She illustrated one probable reason the role caused second thoughts—the way people acted around her when she was wearing the fat suit.
Paltrow said that the first time she ever tried on the fat suit, she walked through a hotel lobby. "It was so sad," she said, "It was so disturbing. No one would make eye contact with me because I was obese.” she said.
She noted that clothes made for heavy women were "horrible," then said she “felt humiliated because people were really dismissive."
No one has asked Jack Black how he feels about this, as far as we know, but he also made Pauly Shore comedy misfire Bio-Dome and something titled Johnny Skidmarks, so it's a sure bet he's not into regretting much of anything.