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Played By: Abigail Breslin
- Adorkable: Has big glasses, an adorable personality, red cowboy boots, pink leopard print shorts, sweatbands and she also comes off as a tad awkward but that just makes her even more endearing.
- Big Eater: She loves to eat, something her father tried discouraging her.
- Burlesque: Her talent performance, much to the horror of everyone watching.
- Cheerful Child: She's always jolly and endearing.
- Children Are Innocent: She doesn't seem to give in to the negativity around her.
- Cry Cute: "Grandpa, am I a loser...?"
- The Cutie: She is obviously not pageant material but she's so adorable, innocent, and determined that you can't help but love her.
- The Heart: She's the glue holding the family together. They may not like each other very much, but they'll all go through hell and high water for her sake.
- Little Black Dress: Wore one in the pageant's evening gown competition.
- Living Emotional Crutch: To everyone. She's pretty much the reason why the Hoovers don't become a Big, Screwed-Up Family by the end. Even when Dwayne has a breakdown, he immediately gets better after Olive hugs him and comforts him.
- Meaningful Name: Olive is a name associated with peace and harmony.
- Meganekko: She has a rather large specs. In fact, that's the very first thing you'll see in the film!
- Morality Pet: Everyone cares for her, and harming her physically, emotionally and psychologically is a huge Berserk Button for them, even against one another.
- Nice Girl: To the point that she sticks out to her bitter and brooding family members.
- Plucky Girl: No matter what kind of crap she and her family goes through and no matter how insurmountable the odds seem against her, she always manages to remain positive and upbeat. Most of the time, anyway.
- Squee!: Does this after being informed that she'll be able to qualify for the titular pageant.
- Static Character: She's the only member of the Hoover family who doesn't undergo any sort of Character Development, being relatively the same person she was at the beginning.
- Supporting Protagonist: Although the film's main plot is to get her to compete in the titular pageant, Olive spent most of the film as a Tagalong Kid and everyone's Morality Pet.
- Tagalong Kid: Justified, as she is the youngest member of the family.
- Token Good Teammate: Nice Girl Olive sticks out to her bitter, brooding and apathetic family members.
- Trademark Favorite Food: Ice cream.
Played By: Greg Kinnear
- Competition Freak: He's obsessed with winning and doesn't want anyone in his family to be a "loser" (despite being a loser himself).
- Determinator: He taught himself and his family to never, ever quit.
- Jerkass: Spends most of the film as a dick to everyone.
- Jerk with a Heart of Gold: Despite this, he does mean well and have his family's best interests in mind.
- Obnoxious In-Laws: He doesn't get along well with his brother-in-law Frank.
- Papa Wolf: When one of the pageant organizers walks onstage and tries to stop Olive from dancing (grabbing her arms), an outraged Richard races to the front of the auditorium, leaps on the stage, jumps on the MC's back and rides him into the wings.
- Parental Abandonment: He has a Missing Mom. Midway to the film, a Disappeared Dad as well.
- The Patriarch: He is the head of the Hoover family.
- Second Love: He is Sheryl's second husband.
- Small Name, Big Ego: Always talk big, despite not being that credible himself.
- Social Darwinist: "There are two people in this world; winners and losers!"
- Supporting Leader: He is The Patriarch of the family, but his daughter is the main character of the story.
- Took a Level in Kindness: Makes a gradual Heel Realization towards the end of the film.
- Wicked Stepfather: He's not really wicked or evil, but Dwayne sees him as this.
Played By: Toni Collette
- The Lancer: Being the family's matriarch, she acts as Richard's Number Two.
- Only Sane Woman: She's by far the most normal member of the family.
- Silk Hiding Steel: She's a "take no crap" kind of woman.
- Smoking Is Cool: Much to her husband's annoyance.
- Team Mom: Well, she is the matriarch of the family.
- Women Are Wiser: She comes off as more normal and reasonable than her husband.
Played By: Steve Carell
- Beard of Sorrow: For starters, he attempted suicide. Apparently, there are a lot of reasons why...
- Cool Uncle: Once he finally gets his act together towards the end of the film.
- Deadpan Snarker: There's a scene where Richard gets annoyed by his sarcastic comments.Richard: Sarcasm is just the sour grapes of losers trying to pull winners down to their level. That's one of the lessons of Step Four.Frank: Wow, Richard! You've really opened my eyes to what a loser I am! Say, how much do I owe you for those pearls of wisdom?
- Driven to Suicide: Attempted this, but failed.
- Fired Teacher: He used to be a college professor prior to being usurped by his rival professor.
- Man in White: He wears an entirely white attire.
- Sixth Ranger: In virtue of not living with the Hoovers.
- The Smart Guy: He used to be a top notch professor, apparently.
- Straight Gay: If he didn't uttered the Word of Gay at the start of the film, chances are, Olive and the audience wouldn't know he is.
Played By: Paul Dano
- Ace Pilot: His main goal is to be a top-notch Air Force pilot.
- Aloof Ally: He hates his own family, or so he claims.
- Atomic F-Bomb: He doesn't handle the discovery his Dream-Crushing Handicap very well.
- Berserker Tears: During his Atomic F-Bomb.
- Beware the Quiet Ones: Despite not speaking, you don't want to piss him off. Once he breaks his vow of silence, he's much more dangerous.
- Big Brother Instinct: He tries to prevent Olive from competing in a contest that he views as oversexualized and demeaning to girls.
- The Big Guy: He constantly works out.
- Brutal Honesty: "Olive's not a beauty queen. She just isn't. I'm gonna go tell her..."
- Cool Big Bro: He really loves his little sister Olive.
- Determinator: During his heart-to-heart with Frank near the end of the movie, he decides that even if he can't join the Air Force, he's still going to learn to fly, colorblindness be damned.
- Eerie Pale-Skinned Brunette: He is notably pale.
- Elective Mute: He has taken a vow of silence until he achieves his dream of becoming an Air Force pilot. He breaks it in the second half of the film.
- Emo Teen: Dwayne has... issues. He even confesses to being a fan of Friedrich Nietzsche.
- Hates Everyone Equally: Or so he claims, but many scenes in the film show that he actually loves his family.
- Jerk with a Heart of Gold: He acts as an Aloof Ally, but cares deeply for his family.
- Nietzsche Wannabe: Literally.Frank: Who is that? Nietzsche? So you stopped talking because of Friedrich Nietzsche? ...Far out.
- No Name Given: His last name is never revealed, though The Other Wiki lists it as Hoover despite being Cheryl's son from a previous marriage.
- Silent Snarker:Dwayne: (writes "I hate everyone" on a pad)Frank: Come on. How about your family?Dwayne: (highlights "everyone")
- Tragic Dream: He's colorblind, thus his dream of being an Ace Pilot is not meant to be.
Played By: Alan Arkin
- Corruption of a Minor: "Fuck a lot of women kid. Not just one woman, a lot of women!" Words he said to his 15 year old step-grandson.
- Dirty Old Man: He still wants to get around to this day, and hates himself for not being able to do so anymore.
- Drugs Are Bad: Unless you're old, according to him.
- Grumpy Old Man: He's easily agitated.
- Hidden Depths: He might act obnoxious most of the time, but he's perfectly capable of displaying wisdom too.Edwin: You know what a loser is? A real loser is someone who's so afraid of not winning, they don't even try.
- Hypocritical Humor: His entire characterization is made of this.
- Jerk with a Heart of Gold: He acts as a bigot and obnoxious, but he cares for his family a lot.
- Killed Offscreen: Olive just says he won't wake up.
- Lovable Sex Maniac: He loves buying Porn Stashes, and Really Got Around in his younger days.
- Mentor Occupational Hazard: He teaches Olive her burlesque dance routine and dies midway to the film.
- Retired Badass: He's a World War II veteran.
- Screw Politeness, I'm a Senior!: He just doesn't have the time or inclination to be respectful anymore and freely says whatever's on his mind.
- Sir Swears-a-Lot: Cluster F-Bomb, proceeded by Precision F-Strike, then Cluster F-Bomb again. You know how the cycle goes now.
- The Smart Guy: The street-smart and "smartass" variant.
Played By: Bryan Cranston
- Manipulative Bastard: He's a typical "smooth-talking businessman" type of character.
- "The Reason You Suck" Speech: Rather, he gave Richard a "the reason you're not viable" speech. What he basically implies is that, even though the Nine Steps program is as corny as can be, it could have still sold a ton of books if Richard at least had name recognition going for him. But, in addition to having a clearly cheesy motivational program, he's an absolute nobody to boot.
- Sharp-Dressed Man: He is a businessman after all.
- Shout-Out: His name and modus.
Played By: Justin Shilton
- Bitch in Sheep's Clothing: Appears concerned about Frank when he runs into him, but appears to mock him with Frank's rival professor when Frank turned his back.
- Only One Name: No last name given.
- Straight Gay: If he isn't revealed to be Frank's ex-boyfriend, you wouldn't know he's gay.
Played By: Gordon Thomson
- The Rival: To Frank.
- Smug Smiler: His picture shows this.
- Straight Gay: He doesn't look stereotypically homosexual either.
- The Usurper: Apparently, he wormed his way to Frank's supposed credits.
State Trooper McCleary
Played By: Dean Norris
- All Men Are Perverts: He's easily Distracted by the Sexy while on duty.
- Badass Biker: Well, he is a state patrol cop.
- Cool Shades: Part of his outfit.
- Dirty Cop: To distract him from his job, all you need is a Porn Stash.
- Distracted by the Sexy: He seems to forget the reason he's arresting Richard after seeing the Porn Stashes.
Pageant Official Jenkins
Played By: Beth Grant
- Aloof Dark-Haired Girl: Towards the Hoovers, at least.
- Eerie Pale-Skinned Brunette: She's very pale.
- Final Boss: She serves as the last obstacle of the Hoover family.
- Get Out!: Orders Richard to get Olive off from the stage. It didn't ended as planned.
- Last-Name Basis: No first name given.
- The Leader: She seems to be the person who calls the shots at the pageant.
- Pink Means Feminine: Her attire.
- Silk Hiding Steel: She's a "take no crap" kind of woman too.
Played By: Wallace Langham
- Nice Guy: Allowed Olive to participate in the titular pageant despite being late and is one of her supporters in the finale.
- Only One Name: No last name given.
- Token Good Teammate: To the pageant staff.
Played By: Lauren Shiohama
- Everyone Calls Him "Barkeep": She's just referred to through her pageant title instead of her name.
- Ms. Fanservice: She is the only beauty queen of right age in the film.
- Nice Girl: She acts very friendly to Olive and the other participants and is one of Olive's supporters in the finale.
- Token Good Teammate: To the pageant judges.
- Token Minority: She is the only notable Asian character in the film.
Pageant Assistant Pam
Played By: Mary Lynn Rajskub
- Defrosting Ice Queen: First acts cold towards Olive, but she's obviously enjoying while watching the Hoover Happy Dance. She doesn't act "cold" so much as "impersonal/professional." She's just doing her job - and clearly not enjoying it all that much.
- Friendly Enemy: She clearly doesn't mind the Hoovers doing their thing.
- First-Name Basis: No last name given.
- Number Two: Hence her job title.
- Token Good Teammate: In virtue of being a Friendly Enemy.
Played By: Matt Winston
- Large Ham: He seems to be enjoying his hosting gig.
- No Name Given: No first or last name from Word of God.
- Sharp-Dressed Man: Well, he is an MC after all.
The Biker Dad
Played By: Geoff Meed
- Badass Beard: He sports one.
- Badass Biker: Enforced with his attire, hence the nickname.
- Delayed Reaction: It took a few seconds before his Incoming Ham.
- Face of a Thug: He has a menacing appearance but is actually a Gentle Giant.
- Gentle Giant: Is quite a large and intimidating fellow, but he is literally Olive's loudest supporter outside her family.
- Guttural Growler: Has a very raspy voice.
- Incoming Ham: "YEAH, ALRIGHT!"
- Jerk with a Heart of Gold: Is aloof and dismissive towards Richard, but becomes Olive's (again, literally) loudest supporter in the audience other than her family.
- No Name Given: The credits only named him as the biker dad.