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Played By: Kevin Spacey
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.
- All Guys Want Cheerleaders: He lusts after the teenaged cheerleader Angela.
- Chivalrous Pervert: Pervert first, then later isn't as desperate and unhappy enough to have sex with his daughter's friend.
- 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: His last words? "Oh man."
- 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.
- Intergenerational Friendship: Forms one with the teenaged Ricky.
- 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.
- Posthumous Narrator: Been narrating his life.
- Sexless Marriage: The only boinking done was masturbating in the shower.
- This Loser Is You: At first, a shabby, desperate, unhappy man with a midlife crisis.
Played By: Annette Bening
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, she slaps her.
- Bitch Alert: Her first onscreen actions are yelling at her husband and remarking that her daughter is trying to look unattractive.
- 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.Carolyn: You think you're the only one who's sexually frustrated?
- 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, was her part, she was about to have sex with Lester until she panicked about a beer stain on the sofa.
- 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.
- Will Not Be A Victim: Invokes this herself on her way to try and kill Lester.
- Your Cheating Heart: With her role model and gets caught by Lester, who is rather finding it funny.
Played By: Thora Birch
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: Oddly has this, though she'd be spilling out of a A cup already.
- Aloof Dark-Haired Girl: She's really detached to 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.
- Ice Queen: Not very warm with her parents, though understandably, not far off.
- 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: Ricky comments on her beauty.
Played By: Mena Suvari
A girl on the cheerleading team with Jane and 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.
- 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 we see that much of what she's been saying is a lie.
- Jerkass: She's vain, self-centered, and puts Jane down a lot.
- The Tease: Deliberately encourages Lester's crush on her because it makes her feel good. When he actually flirts with her back, she immediately gets uncomfortable and leaves.
- Toxic Friend Influence: She keeps Jane around because Jane makes her feel better about herself.
Played By: Wes Bentley
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: He'll film anything and anyone, with or without their permission. Downplayed, in that he knocks it off when Jane asks him to.
- 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.
- Nightmare Fetishist: Films a dead bird "because it's beautiful", and is seen staring in fascination at Lester's dead body.
- "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."
Played By: Peter Gallagher
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.
Col. Frank Fitts, USMC
Played By: Chris Cooper
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.
- 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.
- Knight Templar: His life as a marine seeps into every aspect of his life. He makes his son take drug tests on the regular.
- 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).
- 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.
Played By: Allison Janney
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 & Jim
Jim Berkley & Jim Olmeyer
Played By: Sam Robards & Scott Bakula
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.