Patrick Stewart's Perfect 'Simpsons' Episode Reveals the Beloved Actor's Secret Weapon

Published Oct 31, 2026, 11:00 PM EDT “And now, the final ordeal, the Paddling of the Swollen Ass... with paddles.” — Sir Patrick Stewart Patrick Stewart was the perfect Simpsons guest star Image: Paramount Pictures/courtesy Everett Collection Yesterday, news broke that Sir Patrick Stewart died at age 86. With his background performing Shakespeare and his incredible sense of dignity and gravitas, Stewart is being celebrated primarily for his work as Captain Jean-Luc Picard on Star Trek: The Next Generation, as well as being the perfect man to portray Professor Charles Xavier in the X-Men films. But while he was beloved for the dramatic weight he brought to his roles, it's worth acknowledging that the man pulled off some incredibly memorable comedic performances, one of the first was on The Simpsons, where he guest-starred in the season 6 episode, “Homer the Great.” Written by Simpsons legend Jon Swartzwelder, “Homer the Great” is about Homer (Dan Castellaneta) joining a Freemason-like secret society called the Stonecutters. The episode begins with Homer finding out about the organization and begging to be a member. He’s finally able to join when he finds out his father is already a part of the group. Eventually, because of a birthmark Homer has which resembles the Stonecutters logo, he is elevated to the head of the organization, but prior to that, the Springfield chapter of the Stonecutters is led by the mysterious “Number One,” voiced by Patrick Stewart. Image: 20th Century Television/Disney Number One is the highly dignified leader of the Stonecutters, who runs their meetings and oversees the initiation of new members, but he’s also one of the guys. After Homer is initiated into the organization with a series of humiliating rituals, Number One exclaims, “Now let’s all get drunk and play ping pong!” That was just one of several silly lines given to Stewart. Another memorable one came during Homer’s initiation, when he says, “And now, the final ordeal, the Paddling of the Swollen Ass — with paddles.” Stewart, being the professional he is, delivered those lines with the same dramatic weight he would apply to Shakespeare, which is why the Simpsons writers on the old DVD commentary for “Homer the Great” praised Stewart so deeply. “Patrick Stewart, one of my all-time favorite guest stars on this show,” said Dave Mirkin, who was the showrunner at the time and came up with the premise for this episode. “It’s probably one of our best guest performances, if not the best guest performance because he’s so committed to this character and these jokes and he was just making me roar the entire time. He was so into it. He was so excited to do this. He was having such a great time. He played a very serious character on the Star Trek series and he just so enjoyed this and I just so enjoyed working with him.” A little later in the commentary, after the ass-paddling line was delivered, Mirkin further explained why Stewart was so good. “We gave him all these undignified things to say and yet he filled them with dignity and such commitment. He did it so deadly serious. That’s what I mean by commitment, there was no sign that anything is a joke. He did everything really really real.” Image: 20th Century Television/Disney The impressive thing about the performance is that this appearance was one of the first pieces of comedy Stewart ever did. While he hosted Saturday Night Live the year before, The Simpsons was only his second comedic role. After The Simpsons, however, he seemed to enjoy the occasional foray into comedy, making memorable appearances on Frasier, Family Guy, and American Dad. He also played the narrator on the two Ted films. Perhaps his best comedic performance, however, came on the Ricky Gervais series Extras, where he played a deeply perverted version of himself who was writing a project for himself to star in just so he could see a bunch of women nude. As he did with his Simpsons role, Stewart played all of these silly, undignified characters with the same integrity he’s now being remembered for. He never winked at the camera or did a silly voice or phoned in the effort. While that might seem obvious, it's the reason why some dramatic actors struggle with comedy. Stewart, however, got the joke. I’d even argue that these comedic performances are part of the reason Stewart was so beloved. While he always seemed kind in his interviews, and many of his characters had a trusting, fatherly persona, Stewart could have come off as austere had he not proven, time and again, how much he was willing to make fun of himself for a good laugh.