It certainly had something to do with his time with Russ Meyer, but he also was capable of liking a movie just for the simple reason that it had attractive women in little to no clothing.
Having said all that, The Pirates movies have never really been good. They are all 8 hours long with fight scenes and chase scenes that go on forever and romantic plots that feel out of a Marx Brothers movie. They have also increasingly relied on Depp as the series went on..... to limited returns at best.
I actually saw the second one in a theater, and it was a mistake. They are movies best show on TNT where you can take fifteen minute breaks to fold laundry, go to the bathroom, and check baseball scores on your phone.
He and Russ were friends before they made Dolls. Roger loved his movies from an early age, which probably did flavor his career as a critic. He comprehended that great acting, great writing, and great cinematography were all... well great; but he also appreciated boobs.
I saw the first Pirates. It was OK. I couldn’t help but notice that Depp was basically doing his Hunter S Thompson from Fear and Loathing, which is a much better movie. So I’ve skipped all the rest.