In an attempt to revive his career, he put out a movie a long time ago called Pauly Shore is Dead. The movie is about his character's quest to become an accomplished, Shakespearean actor because he recognizes that he was extremely lucky and doesn't have the skills to save his fading career once the novelty is over.
I can't emphasize enough that he was playing himself, Pauly Shore, but was doing a piss poor job of it because of how bad of actor he was. And the entire plot he was failing to act in revolved around Pauly Shore learning to act in order to revive his career.
It was a strange type of meta-fail that I can't articulate properly. It was very jarring that he recognized that he needed to expand his skills, but refused to do so and would only (poorly) play a character expanding his skills.
A truly cringe-inducing moment came during the closing credits, when he played answering machine messages to the audience in which actors and industry professionals left polite messages saying he was excellent to work with and they enjoyed working on his project. It was painful to see that he wasn't willing to study acting to become an actor, even though he knew he should, but would settle for playing messages to the audience hoping someone would listen to how nice he was to work with and give him a job.
