The Simpsons (1989): Season 16, Episode 16

16 - 16: Don't Fear the Roofer

In the milestone 350th episode, Homer befriends beer-loving barfly and roofer Ray Magini, guest-voiced by Ray Romano. After discovering a shared passion for sandwiches and the Three Stooges, Homer and Ray become inseparable friends. However, Marge believes Ray is a figment of Homer's imagination and enlists the help of Dr. Hibbert to literally "shock" Ray Magini out of Homer's system.