[[folder:Oblong Family]]

!!Bob Oblong
->'''Voiced by:''' Creator/WillFerrell

Born without arms or legs and works at a poison factory owned by [[EvilInc Globocide]]. Despite his deformities he is very chipper and sunny, and is modeled after various fathers from 1950s TV shows.
Tropes associated with Bob:
* BumblingDad
* CloudCuckoolander: In the episode where it's revealed Helga's parents are missing, she mentioned the last time they sent her money it was blue and red. Pickles joked that they were probably in Candyland before Bob goes on to explain that Candyland uses a barter system so if Helga's parents actually ''were'' there, they'd have sent Helga candy canes or gumdrops instead of paper money. All Pickles can do is pat Bob's head and say "My poor baby."
* [[NaiveEverygirl Naive Everyman]]: Bob's optimism sometimes shifts into blind naivety to the point that Pickles has to bring him to his senses.
* ThePollyanna: Despite having no limbs and being in a dead end job, he's very optimistic.

!!Pickles Oblong
->'''Voiced by:''' Jean Smart

A chain smoking alcoholic who was originally a Hill resident but moved to the valley after marrying Bob. All her hair has since fallen out due to the hazardous atmosphere of The Valley, and she is now regarded as an outcast by her former Hill friends. While not bitter about losing her privileged life, she often expresses disdain towards her self-centered former neighbors in the Hills.
Tropes associated with Pickles:
* ActionMom: In "Heroine Addict".
* BaldWoman: Due to the exposure to the pollution of the Valley.
* CloserToEarth: Pickles is arguably more grounded in reality than Bob is (despite being a drunk) and acts as a voice of reason when his optimism shifts into blind naivete. She's also a voice of reason regarding how the Hill people treat Valley folk and is more than aware of what assholes the Debbies, Jared, and Blaine are.
* FallenPrincess: She was a rich girl from the Hills who married and moved in with a Valley boy.
* LadyDrunk
* MamaBear: ''Don't'' mess with her kids.

!!Biff and Chip Oblong
->'''Voiced by:''' Randy Sklar (Biff) and Jason Sklar (Chip)

17-year-old conjoined twins who are attached at the waist and share a middle leg. Biff is a hard worker obsessed with sports, while Chip is more laid back. Biff and Chip each occasionally go into "trances" to give the other brother privacy.
Tropes associated with Biff and Chip:
* AmbiguouslyGay: It is frequently implied that Biff is gay and attracted to their coach (in fact, a DVD-exclusive special about how the show was created stated that Biff was gay and Chip was straight).
** BiTheWay: Although other times the two are seen lusting after girls together.
* BigBrotherBully: On occasion.
* ConjoinedTwins

!!Milo Oblong
->'''Voiced by:''' Creator/PamelaAdlon

The youngest son and the series' protagonist. Often referred to by other kids as a “psycho”, he is afflicted with numerous mental and social disorders and is on "everything from Ritalin to Rogaine." Despite his afflictions, he is a very forthright and benevolent boy, though he envies the Hill lifestyle and wishes to rise above his economic status.
Tropes associated with Milo:
* AttentionDeficitOohShiny
* {{Keet}}
* LoserProtagonist
* MadEye: Also TwitchyEye from time to time.
* TheMentallyDisturbed: A comedic example. According to one episode, Milo has every childhood ailment from attention defecit disorder to "foamy diarrhea" (caused by eating a lot of soap) and has been put on every medication from Ritalin to Rogaine.
* OnlySaneMan: He's one of the few characters in the show who questions the absurdities and injustices around him.

!!Beth Oblong
->'''Voiced by:''' Jeannie Elias

The youngest child and only daughter, and has a warty, elongated growth growing out of her head (which comes from bovine growth hormones. According to the episode "Pickles' Little Amazons," Beth asks the supermarket butcher for flank steaks with no bovine growth hormones because "I don't need another one of these"). Despite her appendage, she appears to be significantly better adjusted than the rest of her family.
Tropes associated with Beth:
* BlackBeadEyes
* DeliberatelyCuteChild
* LittleMissSnarker
* NoMouth: It just vanishes when she isn't talking.
* [[OnlySaneMan Only Sane Girl]]


The one-lunged[[note]][[BodyHorror He coughed the other one up on the first episode, which Pickles mistook for a furball]][[/note]] family cat who chain-smokes cigarettes and wears an uninterested, deadpan expression.
Tropes associated with Lucky:
* SmokingIsCool
* TheStoic
** NotSoStoic: He was noticeably horrified by all those female cats on heat coming after him in "Father of the Bribe."


Milo's narcoleptic dog, a result of perfume used on him during his tenure as a test animal at Globocide.
Tropes associated with Scottie:
* CanineCompanion
* HeavySleeper: Justified in that Scottie was sprayed with a perfume that causes narcolepsy (but no longer causes night blindness or anal leakage).


[[folder:Clubhouse Kids]]

!!Helga Phugly
->'''Voiced by:''' Lea [=DeLaria=]

A fat, toad-like girl who will eat virtually anything. She lives in a fantasy world, believing that she is pretty and popular and that the "Debbies'" actually like her (she seems to stubbornly believe this, as when told that the Debbies hate her, she covered her ears, shut her eyes, and started stomping around humming very loudly).
Tropes associated with Helga:
* BigEater
* ExtremeOmnivore
* FanDisservice
* {{Gonk}}
* IRejectYourReality: She lives in a fantasy world where she's thin and beautiful, has hundreds and hundreds of boyfriends, and the Debbies are her best friends.
* ParentalAbandonment: Though not intentionally. Her parents went on vacation to Europe and their plane crashed, where they had to resort to cannibalism to survive until Milo sparked new interest in finding them.
* PantyShot
* VocalDissonance: How many girls sound like boorish middle-aged men (despite that the voice of Helga is actually a woman)?

!!Creepy Susie
->'''Voiced by:''' Jeannie Elias

A girl who speaks with a deadpan French accent and appears to float instead of walk, as her legs are never shown. She is obsessed with death, and has a problem with pyromania, but it has been revealed she does enjoy hula hoops (even though her stiff movements make it physically impossible for her to use one).
Tropes associated with Susie:
* CreepyGood
* DarkIsNotEvil
* EstablishingCharacterMoment: In the first episode when the kids from the Hills went to burn the clubhouse.
* EeriePaleSkinnedBrunette
* {{Goth}}
* GratuitousFrench: She can be heard mumbling this at times.
* NightmareFetishist: Her very first line on the show was, "Drowning is my third favorite way to die, but they are all good."
* NightmareFuelStationAttendant
* TheStoic
** NotSoStoic: "Whee, whee. What, can't I have a little fun?"
*** Played with as her "Whee's" were in her usual CreepyMonotone.


A one-breasted girl who lacks a lower jaw, causing her to spit and talk with a lisp. Despite her deformities, Peggy is incredibly cheerful and upbeat.
Tropes associated with Peggy:
* [[HasTwoMommies Has Two Daddies]]
* NoMouth: Well, no lower jaw, none that is visible, anyway.
* PluckyGirl
* ThePollyanna


A boy saddled with a dangling, doubled posterior. Standard underwear will not fit him, so he wears his grandmother's old bra like backwards suspenders. He is also known to habitually probe his nose and ears with his finger.
Tropes associated with Mikey:
* ButtMonkey: No pun intended.
* DependingOnTheArtist and OffModel: Does Mikey have two butt cheeks, or three?
* TheGenericGuy


[[folder:Hill Residents]]

!!George Klimer
->'''Voiced by:''' Creator/BillyWest

Bob's rich and snobby boss. He represents the power and arrogance of the people of the Hills. He is very condescending to his employees, especially Bob and James.
Tropes associated with George:
* BadBoss
* CorruptCorporateExecutive
* {{Jerkass}}

!!Pristine Klimer

The wife of George and mother to Jared and Debbie. Pristine was good friends with Pickles before she married Bob, but abandoned her once she went to live in the valley.
Tropes associated with Pristine:
* HartmanHips
* RichBitch
* {{Socialite}}
* StepfordSmiler

!!Jared Klimer

The arrogant son of George and Pristine and brother to one of the Debbies. He likes to taunt The Clubhouse Kids, along with his equally snobbish best friend Blaine.
Tropes associated with Jared:
* AmbiguouslyGay
* TheBully
* JerkJock

!!The Debbies
->'''Voiced by:''' Becky Thyre

A popular clique of identical girls who dress alike, much like the ''Film/{{Heathers}}'' or the also-animated Ashleys from ''WesternAnimation/{{Recess}}''. The Debbies are often cruel to the valley kids, especially Helga who aspires to be accepted by them.
Tropes associated with the Debbies:
* PopularIsDumb
* {{Alpha Bitch}}es
* BlondesAreEvil
* ADayInTheLimelight: Debbie Klimer was the victim of a botched plastic surgery that made her look hideously deformed. The Valley people adopted her until she could get the surgery needed to make her look identical to the other Debbies again.
* GirlPosse
* PinkMeansFeminine
* OnlySixFaces: They're all eerily identical. Lampshaded by Pickles in "Bucketheads" when she answered the door and said, "Either I'm ''really'' smashed or you and your friends look exactly alike."
* ShoutOut: To the {{Film/Heathers}}
* [[ThoseTwoGuys Those Six Girls]]

!!Mayor Johnny "The Mayor" Bledsoe

The town's mayor and a masked pro wrestler, a parody of pro wrestler-turned-elected official Wrestling/JesseVentura. He is corrupt, and his daughter is a Debbie.
Tropes associated with Mayor Bledsoe:
* BallsOfSteel: Subverted when he ordered Mr. Klimer to hit him in the crotch with a golf club. Sure, he looked fine, but his next line states otherwise: "That hurts more than I thought it would."
* CoolMask
* MayorPain


[[folder:Valley Residents]]

!!Anita Bidet
->'''Voiced by:''' Creator/BillyWest

The owner of the bar Pickles frequents, The Rusty Bucket. Her name is a play on the phrase "I need a bidet." It is implied that she is a pre-op transsexual, and though it is made obvious to viewers, none of the characters in the show seem to realize it.
Tropes associated with Anita:
* CrossdressingVoices: She's voiced by Creator/BillyWest.
* PunnyName
* {{Transsexual}}: She's a pre-op trans woman. The money she earns from working The Rusty Bucket (most of which comes from Pickles, thanks to her alcoholism) goes towards her gender reassignment operation (which isn't outright stated, but even the most naive viewer can figure it out).
* UnsettlingGenderReveal: Subverted. Anita is never flat out stated to be a trans woman but that show does make jokes about some of her masculine features. Her friends, for the most part, either don't realize she's trans or they just don't want to make a big deal out of it.
* WholesomeCrossdresser


Bob's hunchbacked co-worker. He is a people-pleaser and lacks self-esteem, buying friends on eBay to attend his bachelor party.
Tropes associated with James:
* ExtremeDoormat
* NiceGuy