A Henpecked Husband and personality-less advertising-magazine wage slave who feels trapped in a shallow and meaningless life. He is the film's Posthumous Narrator and main character, and the story concerns his efforts to find happiness.
- Adopt the Dog: He holds back from taking the girl of his dreams, when he finds out that she's still a virgin.
- All Guys Want Cheerleaders: He lusts after the teenaged cheerleader Angela.
- Burger Fool: He becomes one voluntarily and, unlike his co-workers, seems to enjoy it.
- Cardboard Box of Unemployment: After he succeeds in blackmailing his boss and quitting his boring desk job, he leaves the office carrying a box with his belongings hoisted on his shoulder and pumping his fist triumphantly.
- Character Development: His midlife crisis acts not only as a catalyst that changed Lester, but for most of the major characters in the film.
- Chivalrous Pervert: His obsession over Angela is pretty squick-inducing, but when he actually has a chance to fulfill his fantasy, he stops once he realizes that for all her bravado, Angela is still a virgin.
- Classical Antihero: Lacks initiative, big time. At least at first. See This Loser Is You and Henpecked Husband.
- A Date with Rosie Palms: Twice. First the shower scene, then when he's having dirty dreams about Angela at the middle of the film. Carolyn catches him at the latter.
- Deadpan Snarker: To the nth degree, his response to finding his wife cheating on him is more snarky than enraged.
- Dies Wide Open: His corpse was discovered by Ricky and Jane this way.
- Dull Surprise: Done deliberately to highlight his detachment from the world around him.
- Even the Guys Want Him: He's the object of Frank Fitts' desires. Lester doesn't reciprocate and Frank ends up killing him, but not because of said rejection, but more because He Knows Too Much.
- Fanservice Pack: He starts working out around the second quarter of the film.
- Go Out with a Smile: Lester smiles as he lies dying. He just learned his daughter is happy, and is remembering the good times with his family, when he is murdered.
- The Hedonist: Embraces this lifestyle in the film after being unhappy.
- Henpecked Husband: To say his wife doesn't respect him and he lacked self-respect in the beginning is an understatement.
- The Hero Dies: The movie follows his Posthumous Narration leading to his death.
- I Want My Beloved to Be Happy: Played With regarding his attitude toward Carolyn's affair with Buddy. Lester ultimately seems rather indifferent to the affair itself, and wasn't so much happy for his wife finding happiness with someone else as he was delighted at being able to experience a bit of schadenfreude at seeing his wife, who had adopted a superior-than-thou attitude towards him and pretty much everyone throughout the movie (at least in public) being brought down a peg or two in a rather publicly humiliating fashion through being exposed as an adulteress in front of him and everyone he works with.Lester: Honey it's okay... I want you to be happy. Would you like Smiley sauce with that?
Carolyn: Lester just stop it!
Lester: No no—You don't get to tell me what to do ever again.
- Intergenerational Friendship: Forms one with the teenaged Ricky.
- Madden Into Misanthropy: His Character Development arc goes through this and out the other side before being tragically cut short.
- Meaningful Name: "Lester Burnham" is an anagram of "Humbert Learns".
- Mistaken for Gay: By Col. Fitts, who has the hots for him; he turns him down gently.
- My God, What Have I Done?: When he realizes Angela is a virgin and has been putting up a front.
- My Life Flashed Before My Eyes: Happens to him when he dies."I had always heard your entire life flashes in front of your eyes the second before you die. First of all, that one second isn't a second at all, it stretches on forever, like an ocean of time. For me, it was lying on my back at Boy Scout camp, watching falling stars. And yellow leaves, from the maple trees, that lined our street. Or my grandmother's hands, and the way her skin seemed like paper. And the first time I saw my cousin Tony's brand new Firebird. And Janie... and Janie... and... Carolyn."
- Posthumous Narrator: Been narrating his life.
- Sexless Marriage: The only boinking done was masturbating in the shower.
- Soul-Crushing Desk Job: He works a boring desk job that, along with his troubled marriage, he believes is killing him. As part of his midlife crisis, he blackmails his boss, quits his job, and goes back to flipping burgers, which he finds far more satisfying.
- Tantrum Throwing: Lester throwing a plate of food against the wall.
- This Loser Is You: At first, a shabby, desperate, unhappy man with a midlife crisis.
- Took a Level in Badass: After quitting his job, he begins working out... and standing up to his wife.
Lester's wife, head of a real-estate firm and a Stepford Smiler of alarming caliber.
- Abusive Parent: She's emotionally abusive to Jane, though it doesn't seem to be intentional. Later, during a moment when she's particularly high-strung, she slaps her.
- Being A Jerk Sucks: Behind her demanding, Jerkass attitude, Carolyn is a woman intensely unhappy with her life and with herself for failing to reach her own impossibly-high standards. Best illustrated when she starts to break down after failing to sell a house, and then starts slapping herself.Carolyn: Shut up! Shut up!!
- Bitch Alert: Her Her first lines to her daughter are "are you trying to look unattractive today?" and her idea of congratulating her on her routine is, "you didn't screw up once!"
- Break the Haughty: By the end of the film, this domineering Jerkass is reduced to a sobbing wreck.
- Hidden Depths: Carolyn initially just seems like a perfectionist, snarky wife, but is shown later to have her own wants and needs like Lester does ("You think you're the only one who's sexually frustrated?"). Other scenes imply that her own self-imposed high standards have made her miserable. Lester remembers Carolyn as having once been a happy woman, before her own obsession with being perfect made her who she is now.
- Immodest Orgasm: "Fuck me, your majesty!"
- Jerkass: To infinity and beyond! She has high standards that she makes painfully clear her husband and daughter fall short of.
- Power Hair: Short, layered, feminine hair to fit her image of a go-getting Real Estate Agent.
- Sexless Marriage: Implied on her part. She was about to have sex with Lester until she panicked about a beer stain on the sofa.
- Skewed Priorities: Lester chews her out for being more concerned about beer getting spilled on the couch than having an intimate moment with him.
- Stepford Smiler: On the surface, a successful Real Estate Agent with perfect hair, clothes, and makeup who is perfectly cheery. In reality, she strips her husband and daughter of their self-esteem while being immensely unhappy with herself for failing to reach her own expectations.
- Why Did You Make Me Hit You?: Subverted. She hits Jane but actually stops crying and apologizing as she does so, as Jane was having none of her mother's emotional blackmail.
- Will Not Be a Victim: Invokes this herself on her way to (supposedly) kill Lester.
- Your Cheating Heart: With her role model Buddy Kane, motivated primarily by the state of her unhappy marriage with Lester. When caught by Lester, who finds it rather funny, she seems genuinely remorseful.
Lester and Carolyn's daughter of sixteen years. She resents the way her father has begun to withdraw from her, and, in the very first scene of the movie, takes someone up on an offer to murder him.
- A-Cup Angst: She's looking up breast augmentation on the internet early in the movie. Subverted in that it turns out she is actually well-endowed, but her insecurity comes from the fact that one of her breasts is a little larger than the other.
- Aloof Dark-Haired Girl: She's really detached from others.
- Daddy's Girl: Subverted- she and Lester used to be close, but at the start of the film they barely speak and Jane resents him for his obvious crush on Angela. She even says to Ricky, "It would be nice if I was anywhere near as important to him as she is."
- Deadpan Snarker: She is Lester's daughter and finds plenty to mock, with both parents.
- Defrosting Ice Queen: Towards Ricky, but not to her father.
- Emo Teen: Due to her familial issues, she is a moody, unhappy girl that wears a lot of dark colors.
- Freudian Excuse: She's bratty and aloof towards her parents, but to be honest, they kinda deserve it. Especially Carolyn.
- Head-Turning Beauty: Ricky comments on her beauty.
- Ice Queen: Not very warm with her parents, though understandably, not far off.
- Letting Her Hair Down: When she shows Ricky her breasts, she lets her hair down first. She is also shown with her hair down when she and Ricky have their intimate scene.
- Meaningful Name: Could be a play on Plain Jane, but as Ricky points out, she is beautiful. Opposite of Angela in that she isn't a conventional beauty.
- Progressively Prettier: She wears a lot of makeup to start, but as her confidence grows, she stops putting it on, allowing her natural beauty to shine through.
- Raven Hair, Ivory Skin: Her long black hair contrasts with her pale-white asking.
A girl on the cheerleading team with Jane who quickly becomes the object of Lester's fantasies, causing him to start an intensive work-out regimen in an attempt to seduce her. She acts more worldly and experienced than Jane, and isn't afraid to use her body to advantage.
- All Guys Want Cheerleaders: the first time Lester sees her (and becomes infatuated with her) is when he watches her cheerleading routine.
- Does Not Like Shoes: She's usually barefoot at Jane's house.
- Everyone Loves Blondes: Her claim, and she's right to an extent.
- Fashion Model: what she aspires to be, because "there's nothing worse than being ordinary".
- Have I Mentioned I Am Sexually Active Today?: It's all a lie.
- Hidden Depths: Linked to her Inferiority Superiority Complex. When she's on the receiving end of Ricky's "The Reason You Suck" Speech, her reaction implies that his comments hit a lot of hidden but poorly-managed insecurities. When Jane finally has enough and leaves her, she seems genuinely saddened. Then there's the final reveal that she's actually a virgin, and that her Tease persona is an act. In the end, the seemingly-lustful, sensual Lolita Expy is revealed to simply be a fairly typical teenager: vulnerable and insecure, and trying to seem more experienced and confident than she actually is.
- Inferiority Superiority Complex: Treats Jane like her sidekick and flaunts her looks in front of people her own age, but when Ricky talks to Jane and not her, she complains, "He didn't even look at me once!" However, we see later in the movie that she's actually very vulnerable and insecure, and much of what she's been saying is a lie.
- Jerkass: She's vain, self-centered, and puts Jane down a lot.
- Meaningful Name: Her last name is a homonym for "Haze", inviting comparisons to Dolores "Lolita" Haze, the titular character of Lolita.
- The Tease: Deliberately encourages Lester's crush on her because it makes her feel good. When he actually flirts back, she immediately gets uncomfortable and leaves. This is turns out to be major Foreshadowing of her being a virgin, and much more insecure than she appears.
- Toxic Friend Influence: She keeps Jane around because Jane makes her feel better about herself.
- Unexpected Virgin: Despite having a reputation as someone who Really Gets Around, she has yet to have sex. When Lester learns this when they're about to have sex, he stops himself.
The new next-door neighbor to the Burnhams and Jane's eventual love interest. He is a weird combination of Stalker with a Crush, Cloudcuckoolander and Shrouded in Myth (in regards to where he was before he moved here), and sees more clearly than anyone else in the cast. He is an experienced dealer of marijuana, becoming Lester's supplier, and carries a video camera everywhere to record interesting moments out of his life.
- Camera Fiend: Angela thinks he's this but he films Jane because he thinks she's interesting, and stops when she asks him to. The scene where Jane strips off for him on camera points this out as, while she is topless, Ricky is pointing the camera at her eyes because of her expression.
- Creepy Good: He films people without their knowledge, as well as dead animals (and people), and speaks in a rather quiet, low voice, with a permanent intense stare, and is a drug dealer to boot. But he's actually a good guy (notably, he stops filming as soon as Jane asks him to, and clearly means no harm), and is probably more well-adjusted than most of the cast.
- Freaky Is Cool: Doesn't give a damn what anybody thinks of him.
- Intergenerational Friendship: Strikes up a friendship with Lester, who's old enough to be his father.
- Intimate Artistry: He takes his video camera with him everywhere and views the entire world through the viewfinder. Though extremely creepy and borderline (or over the border) stalking, he is shown growing attached to and connecting with people and experiences much more deeply than any other character. He and Jane Burnham grow closer as he films her.
- Loners Are Freaks: Ironically, he is probably the most normal person in the movie.
- Also an Ironic Meaningful Name: he does not fit. It's not a coincidence that the movie starts when his family moves in next door.
- His backstory is that he had a fit (flying into a rage and attacking another kid) that landed him in a mental hospital, and his father had a fit when he though Ricky was servicing Lester.
- Military Brat: His father is a (retired) military man.
- Nightmare Fetishist: His obsession with "beauty" extends to gazing with fascinated detachment at Lester's corpse lying in a pool of blood.
- "The Reason You Suck" Speech:
- Gives a particularly cutting one to Angela after she's a bitch to Jane one too many times. She runs off in tears.
- Also gives one to his Dad. "What a sad old man you are."
- Stalking Is Love: Played Straight, although he means no harm, and really does love Jane.
Carolyn's main business rival, the self-styled "King of Real Estate." He's powerful, success-minded, has enormously charismatic eyebrows, and appeals to her Stepford Smiler instincts: "In order to be successful, one must project an image of success at all times." Eventually, the two of them start an affair.
- Your Cheating Heart: Begins an affair with a married woman while married himself.
Col. Frank Fitts, USMC
A now-inactive Marine who fought in Vietnam. He's trying to raise Ricky in his own image, which is meeting with limited success. He's also a flaming homophobe.
- Abusive Parents: Regularly beats up his son, not to mention that he had had him committed to a mental institution for two years.
- Armored Closet Gay: Frank is gay himself, but hides it behind an overtly-masculine self-image, confusing masculine behavior for an indicator of heterosexuality.
- Big Bad: Is responsible for Ricky being as weird as he is, and kills Lester.
- Dad the Veteran: Ricky's father and fought in The Vietnam War.
- The Extremist Was Right: While his homophobia and self-loathing are problematic, he is right to make his son take drug tests as he still deals and uses drugs (Ricky gets around it through a deal with a friend for clean urine samples).
- Hidden Depths: He might seem like a disciplined, no-nonsense military man but Frank has an unhappy marriage, an uneasy relationship with his son and serious issues of self-loathing over his homosexuality.
- Karma Houdini: He goes unpunished for beating his son and murdering Lester.
- Knight Templar: His life as a marine seeps into every aspect of his life. He makes his son take drug tests on the regular.
- You Are What You Hate: Frank is homosexual himself, and has spent his entire life hating himself for it, hiding it, and over-compensating for it.
The colonel's silent, disjointed wife. She doesn't get many scenes, but Janney uses even her character's silence to communicate that there are some severe repression problems going on here.
- Broken Bird: She's silent and meek, likely because she's aware her husband is homosexual and she's been helping him live his lie. Or possibly because, although it's not shown, Frank is just as abusive toward her as he is toward their son.
- Cloudcuckoolander: When Frank kicks Ricky out and Ricky is about to leave to run away with Jane, he bids his mother goodbye. She responds, "Wear a raincoat." Which is...good advice.
- Emotionless Girl: Though she does seem withdrawn and restrained, she does show she cares for Ricky.
- The Quiet One: She only has a handful of lines.
Jim Berkley & Jim Olmeyer
A gay couple who are the Burnhams' next-door neighbors on the other side. Bakula has joked that these are the most normal people in the film and the thing is, he's right. They help Lester develop his new work-out regimen.