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- 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: A sad moment comes when she cries and asks "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.
- 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.
- 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.
- 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: (underlines "everyone")
- Tragic Dream: He's colorblind, thus his dream of being an Ace Pilot is not meant to be.
- 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
State Trooper McCleary
Pageant Official Jenkins
Played By: Beth Grant
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
Pageant Assistant Pam
Played By: Matt Winston
The Biker Dad
Played By: Geoff Meed