Paul Simon on Saturday Night Live. Photo: NBC

With a career spanning more than 60 years, there are many moments from the long life of Paul Simon that might be considered highlights. Like winning the first of his 16 Grammys alongside his musical partner, Art Garfunkel. Or like proving to himself that he could successfully navigate the business as a solo artist with the success of his monumental album Graceland. But, if you’re a comedy nerd looking back on Simon’s life, you might consider the real highlight to be that time he wore a turkey costume on live television.

Simon has appeared on Saturday Night Live over and over again throughout the show’s 44 seasons, with four hosting stints, nine musical guest appearances (most recently in the latest episode), and six cameos under his belt. He’s played a part in several iconic moments in SNL history, no doubt owing to two major factors: His music has been an enduring part of American popular culture for as long as he’s been making it, and he’s been close friends with Lorne Michaels for longer than the show’s existence.

According to Paul Simon: The Life by Robert Hilburn, Michaels and Simon were introduced to one another by Edie Baskin, who had been hired as a photographer for what was then known as NBC’s Saturday Night when it was still several months away from its first live broadcast. Baskin invited Michaels to Simon’s house on Long Island, and together they immediately bonded over comedy. “Lorne allowed me to be comedic,” Simon says in the book. The two became fast friends as Michaels attended recording sessions for Paul’s Still Crazy album, and Paul would hang out at pre-production meetings at 30 Rock.

Simon appeared in a very short filmed cameo in the first episode of Saturday Night Live, announcing that he would be hosting the following week’s show. In Tom Shales’s oral history, Live From New York, Simon mentions that he was up for hosting the first one, but Michaels turned him down. “Lorne said, ‘No, let me just work out the kinks on the first show.’” Speaking with Hilburn, Michaels elaborates on this: “It’s always been a strategy of mine to try to make the second show ‘hotter’ than the first because you want the ratings and the word-of-mouth to go up, and I thought Paul could do that.”

The first thing viewers saw as the second episode began was Simon sitting on a stool singing “Still Crazy After All These Years.” As the song continued, suddenly the show’s breakout star and original Weekend Update anchor Chevy Chase appeared as a stagehand, carrying equipment behind the singer. He fell over, looked up, and announced, “It’s Saturday Night!” At this stage in the show’s development, the balance between music and comedy was not quite the same as it is today, and on this night in 1975, the scale tilted way further towards music. Paul was the host, but despite the fact that he wasn’t even that episode’s musical guest (Randy Newman was, if you’re curious), he still managed to perform eight different songs (and “Me and Julio Down by the Schoolyard” shows up in a pre-taped piece he starred in). Notably, this episode marked the first televised reunion of Simon & Garfunkel since their breakup in 1970. Together they performed “The Boxer” and “Scarborough Fair.” Much would be made of later animosity between the two, but here they seem happy, with Simon’s biographer pointing out that Art puts his hand on Paul’s shoulder and Simon “gently [reaches] back to him.”

Simon came back the following season to host SNL in November, right before the Thanksgiving episode, hence the infamous turkey costume. For his post-credits monologue, Simon tromps out in his ridiculous costume and sings a few bars of “Still Crazy” before interrupting himself to talk about having been convinced by the show’s staff to wear the costume. “They said, ‘Hey, you know, you take yourself so seriously. Why don’t you stop taking yourself so seriously for a while and loosen up a little bit, and maybe people will laugh …’ I want to be a regular guy, but I feel this has just been a disaster. I’m sorry. I’m just gonna go and change.” Backstage he meets with Michaels, and Simon declares it one of the most humiliating moments of his life, while Michaels insists it “went great.” Simon storms off, waddling, as Michaels throws to commercial.

In 1977, NBC invited Simon to star in his own variety show, and he turned to Michaels to produce. The Paul Simon Special is basically a Saturday Night Live B-side, with comedic sketches and music from Simon and a star-studded cast; Lily Tomlin, Charles Grodin, Chevy Chase, and SNL writers Al Franken, Tom Davis, and Alan Zweibel all make appearances throughout the hour. This special also features the second reunion of Simon & Garfunkel, who sing “Old Friends/Bookends.” (Unable to get away from the duo, Michaels would produce the film of their 1981 reunion at a free concert in Central Park, as well.) The Paul Simon Special was a one-off, airing once, but lived on on laserdisc, and does today on YouTube.

Simon and Michaels’s friendship resulted in several different opportunities for their careers. When Michaels left SNL during the early ’80s, he created a new sketch show called The New Show and hired singer-songwriter Heidi Berg away from SNL to serve as the bandleader. Once The New Show was canceled, Heidi met with Michaels at his office in the Brill Building to talk about future music opportunities, and he suggested she drop by Simon’s office, which was just down the hall. She would introduce Simon to the world of South African music, which would result in his seminal album Graceland.

Two years later, with Michaels back at SNL, Simon would host and showcase some of his new tracks, and, while there, film a music video for “You Can Call Me Al.” Michaels had a test pressing of the unreleased album at his summer house on Long Island and, according to Laura Jackson’s book Paul Simon: The Definitive Biography, Chevy Chase was visiting his former boss when he played it for him. In the book, Chevy recalls, “Lorne played a couple of songs for me and then told me, ‘Paul’s unhappy with this [first] video. Why don’t you do something?’” He did, and in case you didn’t see it during the thousands of times MTV aired it in the late-’80s, this was the result:

In December 1990, Tom Hanks was appearing as the host of Saturday Night Live for a record fifth time. On this evening he introduced into SNL lore the mythic Five Timers Club, one of “the most exclusive clubs in the world.” He takes viewers on a tour of the club’s elite hang-out, and as soon as he enters the room he is greeted by “Sean,” played by then-writer Conan O’Brien, who adorns Hanks with his club robe. He is then immediately face-to-face with Simon, who at that point had hosted four times (but apparently was allowed in on a technicality with his four separate musical guest appearances). Simon greets Hanks warmly, razzes him about his movie Joe Versus the Volcano, and ushers him into the reading room, where he meets Steve Martin, who, when called “Mr. Martin” by Hanks, corrects him, telling him to call him “Mr. Steve Martin.” In 2018, it would be surprising for an episode of SNL not to have five celebrities on top of the announced host, but in 1990 this was an incredibly rare occurrence. As a result, The Five Timers Club sketch became an enduring part of the show, mentioned by several hosts going forward, and was even reprised in 2013 when Justin Timberlake joined the club, with Simon, Hanks, and Martin reappearing alongside Dan Aykroyd, Chevy Chase, Martin Short, and Candice Bergen. Simon also appeared in a “What Up with That?” sketch during the same episode.)

Perhaps the most important Paul Simon moment in SNL history is also the most somber. Following the attacks of September 11, then-mayor Rudy Giuliani appeared on the September 29th episode with several NYC firemen and police officers to soberly open the show. Giuliani gives a brief speech in which he talks about the resolve of Americans and the importance of freedom, before Simon appears on the second stage to perform “The Boxer” while wearing an FDNY hat in front of a American flag. When he finishes, Michaels joins Giuliani onstage and asks whether it’s okay for the show to “be funny.” The mayor replies “Why start now?”

In an appearance on the podcast WTF, cast member Kenan Thompson talks about stopping at Michaels’s Upper West Side apartment on the way to a Yankees game. He describes it as “crazy,” complete with a private elevator and a door in the kitchen that is connected to his friend Paul Simon’s apartment. Kenan describes it as “cute.” In Live From New York, Simon sums up it differently: “You’re lucky if Lorne is in your life. For the most part, for most people, their life is improved. I know that’s the case with me.” If you count the many cameos and musical appearances, Simon has appeared on his friend’s show 19 separate times. 74-year-old Chevy Chase complained to the Washington Post this September that Lorne told him he was “too old” to host; Simon celebrated his 77th birthday by performing as the show’s musical guest last Saturday. From 1975 to the present day, Paul Simon has been in the DNA of SNL, and as long as Lorne Michaels is still there, that isn’t going to change.