- “I can't believe I spent my Saturday picking up garbage. I mean, half those bottles weren't even mine.”
- “Ow, my eye!”
- ―Lenny's running gag.
- “Eh, everybody makes mistakes, that's why they put erasers in the backs of pencils.”
Lenford "Lenny" Leonard is a recurring character in The Simpsons and a supporting character in The Simpsons Movie. He is the best friend of Carl Carlson and, along with Carl, second best friend of Homer Simpson, behind Barney Gumble. He works at the Springfield Nuclear Power Plant and possesses a master's degree in nuclear physics, but he is portrayed as a simple, often naive, blue-collar working man. Lenny is also one of the few characters allowed to possess a "Simpson's Family" trait: Homer's beard line.
Despite being shown in the First Church of Springfield, Lenny is a Buddhist. Born in Chicago, he is also a war hero and a three-time juror. His grandmother spent 20 years in a Soviet labor camp, hinting that Lenny may have ancestors from the former Soviet Union, or have ancestors who were POWs. In The Simpsons comics number 116 we learn that Lenny is the last surviving descendant of the Woopakanomie Native American tribe. He was a member of the Springfield chapter of the Stonecutters secret society (Number 12, outranking Mr. Burns). Lenny seems to have little regard for his own life: "Quick and pointless, that's the death for me". Another example of his apathy towards salvation is that he shrugs after being pulled from a ladder which would have seen him and
Homer to safety. In "Mommie Beerest", Lenny has a magazine cover from the week of his birth, the headline reads 'Bloodbath in Laos' this means his date birth is possibly in March of 1971, in that date Life magazine published on its cover photos of Laotian Civil War.
Lenny works at the Springfield Nuclear Power Plant alongside Carl Carlson and Homer Simpson. Despite his steady job, Lenny has been featured with several other jobs. On one occasion, he is promoted to head of the power plant when Mr. Burns goes bankrupt; which Smithers later describes to Homer as a "reign of terror". Homer considers Lenny to be the second richest man he knows. However, Lenny is once shown living in a dilapidated house, and pleads with Marge to not tell anyone how he lives. By the time of "Helter Shelter", he has moved to a fancy, well-furnished modern apartment... that happens to share a wall with a jai-alai court. According to him, he finds the sound of the balls hitting the common wall 'soothing'.
In "Lisa's Wedding", it's shown Lenny is once again in charge of the power plant. In one episode, it is implied he is an undercover agent whose target is Homer. He was also fired from the Nuclear Power Plant at least twice, once as a demonstration to Bart as how he should act as his heir, and the second due to being the last one in the designated cabin in a Company Competition. Also, during an Employee Appreciation Night, he attempted to thank Mr. Burns for the great evening, but his attempt backfired due to him being drunk, which only resulted in terrifying his boss.
At the Adult Education Annex, Lenny teaches a class on "How To Chew Tobacco". In one of Homer's daydreams, it's shown that Lenny is President of the United States. In "Homer vs. Dignity", Homer says he is a war hero, implying Military Service.
Lenny is a member of the Republican party, and possesses a Dole/Kemp '96 American flag tattoo. However, he seems to learn on the less extreme side of the political right, as he disliked the reactionary radicalism of Birch Barlow. Lenny is also a successful writer who wrote a series of mystery novels, one of them entitled "The Murderer Did It", which are called "scary good fun" by Stephen King. Lenny is also shown to be a member of the NRA as seen in "The Cartridge Family". His weapon of choice appears to be an AR-15 rifle with a vertical grip, which he says "are manufactured for a reason: to take out today's modern super animals like the flying squirrel, and the electric eel." 
Lenny is an adept guitar player. According to the episode "That '90s Show", Lenny was a guitar player for his friend Homer's Grunge band, Sadgasm. The band split up some time after the release of their song "Margerine".
Though only a lowly nonentity at Springfield Nuclear Power Plant, Lenny holds an exceptionally high ranking position at the local Stonecutters's Lodge -- 17 points above Mr. Burns, in fact. Due to his exalted status in this secret order, Lenny enjoys the gratifying privilege of squeezing Mr. Burns's nose whenever he feels like it, which he never does.
A running gag throughout the series is that Lenny frequently hurts his eye, usually causing him to exclaim "Ow, my eye! I'm not supposed to get [object name] in it!".
In "Flaming Moe's", his head gets set on fire.
In "Homer at the Bat", he gets hit in the knee by a baseball bat.
In "Last Exit to Springfield", Homer punches him in the back of the head, causing him to spit out his coffee.
In "Monty Can't Buy Me Love", he gets stabbed in the head by a coin.
In "G.I. D'oh", he gets run over by a tank.
In "Bobby, It's Cold Outside", he gets caught in a gunpowder explosion.
Little is known about Lenny's family, although it is said that his mother loves both Carl and Moe better than him. She also states that she wishes Carl were her son. The feeling is mutual.
He once stated that his father died in a war, but he doesn't know in which.
Lenny's best friend is Carl Carlson, as they are rarely seen apart; his other friends are Homer, and regulars at Moe's including Barney Gumble and Moe Szyslak. On Lenny's birthday, his friends attempted to throw a surprise party for him at Moe's, which is ruined by Homer, who then sits on a cake shaped like Lenny's favorite bar stool. Homer repeatedly confuses Lenny and Carl, and is shocked
to learn on one occasion that Lenny is white, and Carl is black. To guide himself, Homer has "Lenny = White, Carl = Black" on his hand. He once muttered to himself, "Is that right?" while reading it. Homer once exclaimed, "That's Lenny? I wanted the black one!". When Mr. Burns appears on a radio show in an attempt to boost his popularity, Homer tells him that he has a list of jokes explaining the differences between white and black people; Homer later stated, "White guys have names like Lenny, whereas black guys have names like Carl."
Lenny appears to be well liked by the Simpson family. On one occasion, Marge and the kids built a prayer shrine for him when learning he was taken to the hospital. When Homer went bowling but tells Marge that Lenny was hospitalized; Marge informs the kids, they respond the same way she did and shout, "Not Lenny!"  The Simpson family had a cake inscribed "Happy Labor Day Lenny".
Marge has a picture of Lenny in her hair. In The Great Louse Detective, Lenny tells Sideshow Bob to kill Bart. It is also shown that Lenny greatly values all his friends when he throws them a lavish party (after winning on a lottery ticket) to celebrate their amity.
Relationship with Carl
The possibility of a sexual relationship between Lenny and Carl has constantly been alluded. When Marge's Popsicle stick sculptures of Lenny and Carl are destroyed and mashed together, Lenny stated, "I don't know where Carl ends and I begin!", to which Carl replies, "See, it's statements like that that make people think we're gay." However, in one of the recent episodes, Carl and Lenny are seen to be holding hands when they are in a limo with Marge and Homer trying to cheer up Moe.
When Lenny saw heaven, and Carl asked 'Hey, what does it look like?' we see hundreds of Carl- Angels saying 'get up Lenny, it's time for work'.
Carl once told Seymour Skinner that "Marriage is gonna be great. Now you'll have someone who'll rub your back - without being asked" while glaring at Lenny, who sighed "Oh, not this again." Carl then responds "Yes, this again." When Homer opened a chapel for gay couples after Gay Marriage was legalized, he speculated that Lenny and Carl might be interested, and Marge responds with "Don't you push them - they've gotta work that out for themselves." Once, Chief Wiggum remarked that Lenny's relationship with Carl is on the rocks.
While helping Lisa with a science project, Homer quoted to Lisa "You and science go together like Lenny and Carl - the science is Carl". Another time, Lenny and Carl saw Homer and Marge kiss, prompting Lenny to remark, "Remember when we used to kiss like that, Carl... with our respective girlfriends?" They then discuss what happened to them. Apparently one turned out to be a prostitute and one died. In the Simpsons Game, if the player fails to rescue Lenny and Carl in Lisa the Tree Hugger, Carl might say, "Tell Lenny... I loved... his recipe for caramel sundaes."
Lenny's hero worship over Carl has reached a mounting point. Lenny revealed that he carved Carl's face on a mountain, and called it Mount Carlmore. He later leaves a burning oil field, only because Carl arrived. On one occasion, the residents of Springfield see the stars, and see deep within their hearts and souls; Lenny sees Carl's face in the stars (Carl also sees himself there). Lenny published a newspaper called The Lenny-Saver with the headline: "The Truth About Carl: He's Great." After displaying this, he shed a tear and stated that "it had to be told." Lenny and Carl were once pictured driving a sports car through the woods with two children in the back of contrasting background (either noting they are both single parents have separately or otherwise adopted children).
Carl Carlson states that he and Lenny have the same mother when a major fire is closing in on her work. When Lisa brings back the stars, Lenny sees a constellation of Carl's face.
It should be noted that all of these examples could just be for comedic purposes, as only their heterosexual exploits have been explicitly confirmed. One time Carl and him drunkenly suggest to Barney that he take them to the Playboy Mansion and the Girls College, respectively. In addition, Homer has mentioned that Carl and Lenny have mistresses they spend time with, and both Lenny and Carl were clearly aroused by the female stars of Lemony Lick-It's A Series of Horny Events when they accidentally stumbled upon the filming of the film and were also shown to be extremely willing to take up Homer's bribe of giving them roles to buy their silence to Marge, they're opting to be the foul-mouth boy and do the sex scenes with the girls, respectively. In addition, when Homer was describing a movie he saw that weekend regarding a buxom blonde (implied to be the same movie Mr. Burns held disgust over due to her being "naked as a jaybird" for half the film), Lenny, alongside Carl, acknowledged that it was "their kind of film" in bemusement, while also proceeding to oink (alluding to Mr. Burns' earlier claim of how the unwashed masses will "oink for more" regarding over-sized breasts and a happy end.).
Lenny is apparently divorced - Carl says that he sang "The Best Is Yet to Come" at Lenny's wedding, although it was later shown that Lenny punched Carl for giving a bad speech at his wedding. Lenny is a persistent bachelor who has poor luck with women. Lenny once shaved the legs of a woman who calls him an idiot for not shaving in an upward direction. Homer mentioned to Moe that both Lenny and Carl are with their mistresses. In yet another occasion, he was seen in the opening scene with his arm around a woman
who appears to be his girlfriend. It's revealed that he had dated a woman in a Woody Woodpecker outfit at a fairground for three months until she left him for the man who cleans the vomit on the roller coaster. Lenny had told Carl that he was married to a Beauty-Queen, but it is later revealed that Lenny made his Beauty-Queen wife up, and is unmarried.
It is mentioned once, that Lenny dated a girl named Doreen, but decided to break up with her. He had no courage to do it, so he asked Homer to "dump his girlfriend for him". According to Moe, Doreen cheated on Lenny with everyone, except for him, even though Moe showered her with gifts.
Lenny is also part of "The Guys".
Non Canon Appearances
In "Lisa's Wedding", Lenny is shown in charge of nuclear plant.
At age 47, Lenny owns a super pet. When Milhouse (with giant muscles) gets trapped between two trees, he and Carl leave him there. In Homer's dream in "The Wizard of Evergreen Terrace", Lenny is shown at Homer's funeral as president and when Homer wakes up, he asks Marge not to vote for him.
In "Holidays of Future Passed", Lenny switches brains with Carl because he wanted to get back together with his wife who was sleeping with Carl at the time, but she switched with a monkey on Japanese game show.
In "Behind the Laughter", Lenny and Carl are constant companions, and Bart had apparently paid the two to kiss one another. They then question whether they ever received the money from Bart for doing so, and upon realizing that they were never paid, both gain a worried expression.
In "Treehouse of Horror XVI", Lenny dies and sees the angels in Heaven take the form of Carl (although they're saying, "Hurry up or we'll be late for work at the plant!"). Lenny is killed by killer dolphins in the "Treehouse of Horror XI" segment "The Night of the Dolphin".
In The Simpsons: Hit & Run Lenny appears in Level 1 mission, Office Spaced. Homer goes to a local Krusty Burger to ask Lenny where Mr. Smithers is. He can also later be found standing with Carl later in the level prior to the mission, The Fat and the Furious.
In The Simpsons Game, Carl and Lenny are shown arguing while bird-watching, and having forgotten Lisa and Bart's names when they save Lenny and Carl from logging machinery, even though Lenny and Carl have known them all their lives. Later on both Lenny and Carl can be recruited by Marge in her mob to ban the sales of the Grand Theft Scratchy game to minors.
- Commentary for "Principal Charming"
- Homer the Great
- Half-Decent Proposal
- Simpsons Comics
- Hello Gutter, Hello Fadder
- Bart-Mangled Banner
- Sideshow Bob Roberts
- The Boys of Bummer
- The Cartridge Family
- Helter Shelter
- Monty Can't Buy Me Love
- Hello Gutter, Hello Fadder
- Sleeping with the Enemy
- Pranksta Rap
- Double, Double, Boy in Trouble
- Fat Man and Little Boy
- Marge and Homer Turn a Couple Play
- Half-Decent Proposal
- Lisa the Drama Queen
- Little Big Girl
- "The City of New York vs. Homer Simpson"
- "Team Homer"
- "The Bonfire of the Manatees"
- "Homer Defined"
- The Bart of War
- Marge on the Lam
- Team Homer
- Homer the Smithers
- Homer Simpson, This Is Your Wife
- In Marge We Trust
- Homer and Lisa Exchange Cross Words
|Chief Wiggum ● Lou ● Eddie|
|Bobo ● Officer Sniffy ● Laddie ● Scraps|
|Marge Simpson ● Gloria ● SpringShield: (Homer Simpson, Lenny Leonard, Carl Carlson) ● Santa's Little Helper|