Lists of fan-favorite characters from The Simpsons often include Mr. Burns, Cheif Wiggum, Moe Szyslak, Seymour Skinner, Krusty the Clown, and, of course, the members of the eponymous family. After 34 years on the air, the residents of Springfield have come to feel like family; almost all of them have received at least one episode focused on their own stories, and many of them have garnered ardent followings from the show’s dedicated fan base. There is one character, however, who rarely cracks viewers’ list of favorites, and is still yet to receive much of an arc dedicated to himself, but his contributions to the show are both quietly hilarious and fascinatingly unique.

Lenny Leonard made his debut on The Simpsons in “Life On The Fast Lane,” the ninth episode of the show’s first season. Voiced by Harry Shearer, Lenny first appears making small talk with Homer over lunch at the nuclear power plant. From there on, he became a regular co-worker and bar buddy of Homer’s, frequently appearing at both the plant and Moe’s bar. In the early seasons, this is essentially the extent of Lenny’s character. He is an innocuous everyman, there to fill in the everyday scenes of Homer’s life. As the series carries on, though, that very banal persona becomes a source of peculiar amusement and, eventually, pure hilarity.

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Lenny Leonard: Springfield’s Regular Guy In Residence

While so many other Simpsons characters are rooted in stereotypes, Lenny is a bit more postmodern. Playing the everyman for so long, his shtick has gradually evolved into something self-reflective of his overly regular identity. This is first highlighted in the Season 8 episode “Hurricane Neddy,” when Flanders loses his temper at the Springfieldians, pointing out each of their flaws. When he gets to Lenny, he says, “I don’t know you, but I’m sure you’re a jerk.” To this, the befuddled Lenny responds, “Hey, I’ve only been here a few minutes, what’s going on?” The exchange shows Lenny as one of the town’s few innocently normal residents.

This same play on Lenny’s regular-guy persona resurfaces in Seasons 9 and 10, albeit with a bit more darkness. In the episode “Realty Bites,” Lenny is found living in a dilapidated house, eating canned food by himself in his underwear. When Marge sees him like this, he nervously pleads, “Please don’t tell anyone how I live.” Then, in “They Saved Lisa’s Brain,” after Springfield decides to remove all green lights for budgetary reasons, Lenny is seen rushing through a yellow light. Making it through the intersection, he exclaims, “I’m making record time,” before melancholically adding, “If only I had some place to be.”

These moments reflect how Lenny’s lack of distinguishing character traits have left him lonely and purposeless. However, his loneliness is not tropishly exaggerated like that of the Comic Book Guy, Hans Moleman, or Selma Bouvier. Instead, it is subtle and unexpected, presented in a way that average viewers can identify with. He showcases the unsexy, directionlessness of all the world’s background characters. In the episode “Trouble With Trillions,” when Moe asks him how he would use a free wish, he responds, “I always wondered what it would feel like to wear something that’s been ironed.” Evidently, Lenny doesn’t live a life of luxury, but one of messy plainness, much like people in the real world.

Lenny and Carl: ‘The Simpsons’ Not-So-Dynamic Duo

Of course, one cannot consider Lenny Leonard without also thinking of Carl Carlson. Recast from Hank Azaria to Alex Désert in 2020, Carl is another longtime co-worker and drinking chum of Homer’s. Like Lenny, Carl is usually there to fill in space alongside Homer. Because of their commonalities, Lenny and Carl have become all but inextricable from each other on the show. Hardly is one ever seen without the other.

After so many years of Lenny and Carl appearing side by side, their close relationship has become a source of humor in and of itself, but while Carl has largely retained his coolness over the seasons, Lenny has seemed to develop a latent obsession with his best friend. In “Treehouse of Horror XVI,” Lenny dies and sees heaven as being populated with angels resembling Carl, all saying in unison “Hurry up, or we’ll be late for work at the plant.” It is another jab at Lenny’s trite co-worker identity, as well as a crack at his closeness with Carl. In Season 13, viewers also learn that Lenny carved Carl’s face into a giant mountain on the outskirts of Springfield, dubbed Mount Carlmore. He explains that he carved it “one wonderful summer,” and when Homer asks him what Carl thinks of it, Lenny responds, “You know, we’ve never discussed it.”

Lenny’s Wholesome Love For Carl

Lenny points out Mount Carlmore after Homer expresses his longing for Marge, thus suggesting a romantic element between the two plant workers. This potential bond is not lost on the show, but instead of explicitly confirming or denying them as a couple, Lenny and Carl’s relationship constantly subverts expectations. In the episode “Large Marge,” Carl comments on Marge’s attractive plastic surgery by saying, “This is the longest I’ve ever gone without looking at Lenny.” Then, while at a ballgame in Season 17, Carl and Lenny watch the kiss-cam, and Lenny asks Carl, “Remember when we used to kiss like that… with our respective girlfriends, of course?”

The only outright statement regarding their sexualities comes in Season 18, when sculptures of the two characters fall on Lenny. Lenny then exclaims, “I don’t know where Carl begins and I end,” to which Carl assertively responds, “See, it’s statements like that that make people think we’re gay.” While Carl’s not denying anything, his tone suggests that he (at least) sees the relationship as platonic. This makes Lenny’s attitude towards Carl even funnier. If there is romantic attraction, then Lenny is oblivious to Carl’s disinterest. If there isn’t, then Lenny seems unaware of the connotations of his statements about Carl. Either way, Lenny is a charming simpleton — even through “Homer’s Enemy” confirmed that both he and Carl hold master’s degrees in nuclear physics.

Lenny’s wholesome attitude towards Carl is perhaps best showcased in the Season 15 episode, “Fraudcast News,” where Lenny starts a newspaper called The Lenny Saver. He claims that the paper will reveal the truth, and as he unravels the front page it reads, “The Truth About Carl: He’s Great!” Whether or not he feels romantic attraction towards Carl, Lenny clearly has genuine affection for his friend, which is both uplifting and refreshing.

Lenny’s Surreal Humor Remains Timely in The Aging Show

Like most Simpsons characters, Lenny still has a recurring gag. He tends to get random things stuck in his eye, such as pudding, springs, and jigsaw puzzle pieces. While funny, however, this is far from Lenny’s entire shtick. Instead, Lenny occupies a borderline surreal place, not fitting any archetype, but delivering humor with his nondescript ordinariness. In this way, he more like a contemporary sitcom character out of The Office, Scrubs, or Ted Lasso than one out of the conventionally outrageous Simpsons.

One of the more telling aspects of Lenny’s modernity is the fact that he developed his humor relatively late in the series’ long run. While most of The Simpsons characters grew into their own during the second, third, or fourth season, and peaked between then and Season 8, Lenny began blossoming after the show’s golden years. As late as Season 11, the show mocked Lenny’s lack of personality when Homer lies to Marge that Lenny is in the hospital. To humorous effect, Marge replies in horror, “Not Lenny! Not Lenny!” and when she shares that she has bad news about Lenny, the kids respond in kind. Later, when she learns that Homer lied to her, she is seen sewing get well-quilts for Lenny, and says, “You shouldn’t have lied to me. But I’m just so relieved that Lenny is okay.”

The joke here is that, up through this point, Lenny has been of little to no concern to Marge, the kids, or pretty much anyone on the show. Their genuine grief over his potential injuries is thus unexpected and ironic, for the show’s best Lenny moments were still yet to come. Because the character is such a late bloomer, however, his humor is fresher than others’ on the show. While recent seasons of The Simpsons have been accused of excessively Flanderizing many of its characters (the term literally getting its namesake from Ned Flanders), Lenny remains closer to his prime. In fact, the Flanderization of Lenny’s ordinary-guyness next to Carl actually contributed to his late success, allowing him to go from a nondescript background character to one of the show’s most relatable, endurant, and underrated features.