Five Man Band / Video Games O to S
aka: Video Games O-S

The Leader/Team PetChibiterasu
The LancerKuni
The Big GuyManpuku
The Smart GuyNanami
The ChickKagu
Sixth Ranger TraitorKurow

Paper Mario: The Thousand-Year Door
The LeaderMario
The Smart GuyGoombella
The LancerKoops
The ChicksFlurrie and Vivian
Team PetYoshi
The Big GuyBobbery
Sixth RangerMs. Mowz

Persona: This is assuming that one is playing both routes and making use of every available character at least once. (It's worth noting that according to the sequel, this is exactly how it happened.)

The LeaderThe Main Character
The LancerReiji Kido
The Smart GuyKei Nanjo
The Big GuyMasao "Mark" Inaba
The ChickMaki Sonomura

Snow Queen Quest
The LeaderThe Player Character
The LancerYukino Mayuzumi
The Smart GuyEriko "Elly" Kirishima
The Big GuyHidehiko "Brown" Uesugi
The ChickYuka Ayase

Persona 2 Innocent Sin: The final party
The LeaderTatsuya
The LancerEikichi
The Smart GuyJun
The Big GuyLisa
The ChickMaya

Persona 3: SEES initally fits this trope, but is soon broken by the new recruits.
The LeaderThe Protagoinst
The LancerJunpei
The Smart GuyMitsuru
The Big GuyAkihiko
The ChickYukari

Persona 4
The LeaderYu Narukami
The LancerYosuke Hanamura (Chie could count as well)
The Smart GuyNaoto Shirogane
The Big GuyChie Satonaka and Kanji Tatsumi
The ChickYukiko Amagi and Rise Kujikawa
Team PetTeddie

Planescape: Torment (Note: Because you can have a party of up to six, and there are up to seven NPCs to choose from, some positions have multiple options.)
The LeaderThe Nameless One
The LancerMorte, Annah
The Smart GuyDak'kon
The Big GuyVhailor
The ChickNordom, Fall-from-Grace
Sixth RangerIgnus

Pokémon Ranger (the original)
The LeaderThe Protagonist
The Smart GuySpenser
The Big GuyCameron
The ChickElita
The LancerJoel

Princess Waltz
The LeaderArata Fukamori, Chris Longfield (and Iris)
The LancerAngela Victorie Blendin
The Big GuyLiliana "Lun-Lun" Guenther (in terms of temperament)
The Smart GuyLiesel Hansel
The ChickShikikagura Suzushiro
Sixth RangerShizuka Wisley

Radiant Silvergun
The LeaderBuster
The LancerGuy
The Big GuyTengai
The Smart GuyCreator
The ChickReana

Ragnarok DS
The LeaderAles
The LancerLucifi (Ironically, his in-game class is Swordman, but his advanced class can specialize on spears.)
The Big GuyViselc (Don't get fooled by his appearance; his advanced class, Assassin, is at times [[Genius Bruiser played using a good amount of Strength.)
The Smart GuyLisir (To the letter.)
The ChickSienna (She practically incarnates the concept... given she plays it straighter than a straightedge.)
The MedicRolek (Not a story character, but the poster child of the healing class, Acolyte.)
The Sixth RangerNina, THE MERCHANT OF JUSTICE!!!
Tagalong KidDan (the Taekwon Kid)

Ratchet & Clank Future: A Crack In Time
The LeaderRatchet
The LancerAlistair Azimuth
The Smart GuyClank, Sigmund (a.k.a. Sigma 0426A)
The Big GuyCaptain Qwark
  • Note: The Chick is Talwyn Apogee, but she only has a part in the prequel.

Resident Evil
The LeaderChris Redfield or Jill Valentine depending on the game
The LancerIn Chris's game Jill, or in Jill's game Chris
The Smart GuyBrad Vickers
The Big GuyBarry Burton
The Chick/The MedicRebecca Chambers
Sixth Ranger TraitorCaptain Wesker
Sacrificial LambJoseph Frost

Rise of Legends
The LeaderGiacomo
The LancerLenora, sometimes Carlini
The Big GuyKakoolha
The Smart GuyCarlini
The ChickArri

Riviera: The Promised Land
The LeaderEin
The LancerFia
The Big GuySerene
The Smart GuyCierra
The ChickLina

Rock Band
The LeaderGuitar
The LancerBass
The Big GuyDrums
The ChickVocals
The Smart Guy/Sixth RangerKeyboard

Rogue Galaxy
The LeaderJaster Rogue
The LancerZegram Ghart
The Big GuysLilika and Deego
The Smart GuySteve
The ChickKisala
Plucky Comic ReliefSimon
Sixth RangerJupis (also The Scrappy)

Saints Row 1
The LeaderJulius Little
The LancerTroy Bradshaw
The Smart GuyDexter Jackson
The Big GuyJohnny Gat
The ChickLin
Sixth RangerThe Protagonist

Saints Row 2
The LeaderThe Protagonist
The Lancer / The Big GuyJohnny Gat
The Smart GuyPierce
The ChickShaundi
Tagalong KidCarlos

Samurai Warriors 3: Tokugawa Shogunate at Sekigahara, if you are controlling them
The LeaderTokugawa Ieyasu
The LancerHattori Hanzo
The Big GuyHonda Tadakatsu
The Smart Guy/Sixth RangerKuroda Kanbei
The ChickInahime
The Sixth Ranger TraitorKatou Kiyomasa (considering he went back to defending Toyotomi after Sekigahara)

Shadow Hearts
The LeaderYuri
The LancerKeith
The Big GuyMargarete
The Smart GuyZhauzen
The ChickAlice
Tagalong KidHalley
Spirit AdvisorKoudelka

Shadow Hearts: Covenant
The LeaderYuri
The LancerKarin
The Big GuyJoachim
The Smart GuyGepetto
The ChickLucia
Sixth RangerKurando
Team PetBlanca
Tagalong KidAnastasia
The MentorRoger

Shining Force II (early in the game)
The LeaderBowie
The LancerChester
The Big GuyJaha
The Smart GuyKazin
The ChickSarah

Shining Force III: The Three Scenarios

scn #1
The LeaderKing Benetram
The LancerSynbios
The Big GuyDantares
The Smart GuyGrace
The ChickMasqurin

scn #2
The LeaderMedion
The LancerCambell (doubles as The Big Guy)
The Smart GuySir Grantack
The (other) Big GuyUryudo
The ChickSynthesis

scn #3
The LeaderGracia
The LancerJulian
The Big GuyDonhart
The Smart GuySir Brisby
The ChickKate

Skies of Arcadia
The LeaderVyse
The LancerAika
The Big GuyDrachma
The Smart GuyGilder (also The Mentor)
The ChickFina
The Sixth RangerEnrique

Snowboard Kids
The LeaderSlash
The LancerJam
The Big GuyTommy
The Smart GuyWendy (also the Sixth Ranger)
The ChicksNancy and Linda
The (other) Sixth RangerShinobin

StarCraft I: Brood War Protoss
The LeaderZeratul
The LancerArtanis
The Big GuyThe Executor
The Smart GuyAldaris
The ChickRaszagal
Sixth Ranger TraitorKerrigan

StarCraft II: Raynor's Raiders
The LeaderJim Raynor
The LancerMatt Horner
The Big GuyTychus Findlay
The Smart GuysEgon Stetmann and Rory Swann
The ChickAriel Hansen
Sixth RangerGabriel Tosh

StarCraft II: Heart of the Swarm
The LeaderKerrigan
The LancerZagara
The Big GuyDehaka
The Smart GuyAbathur
The ChickIzsha

StarCraft II: Legacy of the Void
The LeaderArtanis, Hierarch of the Daelaam
The LancerVorazun, Matriarch of the Dark Templar
The Big GuyAlarak, Highlord of the Tal'darim
The Smart GuyKarax
The ChickRohana

Star Wars: The Old Republic

Trooper class
The LeaderThe Trooper
The LancerLieutenant Jorgan
The Big GuyM1-4X
The Smart GuysSergeant Yuun and Tanno Vik
The ChickSergeant Dorne

Smuggler class
The LeaderThe Smuggler
The LancerRisha
The Big GuysBowdaar and Akavi
The Smart GuyGuss
The ChickCorso

Jedi Consular class
The LeaderThe Jedi Consular
The LancerZenith
The Big GuysQyzen and Iresso
The Smart GuyTharan
The ChickNadia

Sith Warrior class
The LeaderThe Sith Warrior
The LancerJaesa Wilsaam
The Big GuyLieutenant Pierce
The Smart GuyMalavai Quinn
The ChickVette
Sixth RangerBroonmark

Sith Inquisitor class
The LeaderThe Inquisitor
The LancerAndronikos Revel
The Big GuyKhem Val
The Smart GuyTalos Drellik
The ChickAshara Zavros
Sixth RangerXalek

Imperial Agent class
The LeaderThe Imperial Agent
The LancerEnsign Temple
The Big GuyKaliyo Djannis
The Smart GuyDoctor Lokin
The ChickVector Hyllus
Sixth RangerScorpio

Bounty Hunter class
The LeaderThe Bounty Hunter
The LancerTorian Cadera
The Big GuySkadge
The Smart GuyGault Rennow
The ChickMako
Tagalong Kid/Team PetBlizz

Stranded (cell phone game)
The LeaderMark
The LancerIsabelle
The Big GuyIan
The Smart GuyMike
The ChickEmily
Kid SidekickStephie

Suikoden I: The early stages
The LeaderTir McDohl
The LancerTed
The Big GuyPahn
The Smart GuyCleo (would be the standard chick, but she's the one who's thinking in the party)
The ChickGremio (worries too much about Tir)

Suikoden III

12th Defence Force Unit of Harmonia:
The LeaderGeddoe
The LancersAce and Queen
The Big GuyJacques
The Smart GuyJoker
The ChickQueen, later Aila
Sixth RangerAila

The Six Knights of Zexen:
The LeaderChris Lightfellow
The LancersBorus Redrum and Percival Fraulein
The Big GuyLeo Gallen
The Smart GuySalome Harras
The ChickRoland Lesaurus
Tagalong KidLouis Keeferson

Budehuc Castle:
The LeaderThomas
The LancerCecile/Juan
The Big GuyJuan/Cecile
The Smart GuyPiccolo
The ChicksMartha, Muto
Team DadSebastian

The vagabond dogs:
The LeaderKoroku
The LancerKoichi
The Big GuyKosanji
The Smart GuyKogoro
The ChickConnie

The Grassland clans:
The LeaderKaraya
The LancerAlma Kinan
The Big GuyLizard
The Smart GuyDuck
The ChickChisha
Sacrificial LionSafyr

Super Mario 64 DS
The LeaderMario
The LancerLuigi
The Big GuyWario
The Smart GuyYoshi
The ChickPrincess Peach

Super Mario Galaxy: The Toad Brigade
The LeaderRed Toad
The LancerPurple Toad (He's actually the most useful because he receives your letters.)
The Big GuyGreen Toad (He's a hard worker and carries a pickax.)
The Smart GuyBlue Toad (He wears glasses and is the most inquisitive/contemplative.)
The ChickYellow Toad (He is the one that dances or whines when not taking a nap.)

Super Mario RPG
The LeaderMario
The LancerMallow
The Big GuyBowser
The Smart GuyGeno
The ChickPeach (a.k.a. Toadstool)

Super Paper Mario
The LeaderMario
The LancerLuigi
The Big GuyBowser
The Smart GuyTippi
The ChickPeach

Super Robot Wars: ATX Team, from the beginning to the end
The LeaderKyosuke (Alt Eisen pilot)
The LancerExcellen (Weissritter pilot)
The Big GuySanger (Dygenguard pilot, also The Mentor... at least at first)
The Smart GuyBullet (Ko Ryu Oh pilot, not quite 'too smart', but he's one of the guys who makes the most sense)
The ChickKusuha (Ryu Ko Oh pilot, serves as The Medic at first)
Sixth RangerLamia (Angelg pilot)

Super Robot Wars Alpha: Project TD girls
The LeaderIbis (Pilot of Altairlion)
The LancerSleigh (Pilot of Vegalion)
The Big Guy/Sixth RangerSelena (Pilot of Soleares and later Alegrias)
The Smart GuyTsugumi (Sub pilot of Altairlion)
The ChickIrui (Non-combatant)

Super Smash Bros. Brawl: The Subspace Emissary

Meta Knight's first team
The LeaderMeta Knight
The LancerMarth
The Big GuyIke
The Smart GuyLucas
The ChickPokémon Trainer
Team PetsSquirtle, Ivysaur and Charizard

King Dedede's Team: What happens when you go through Subspace without saving anyone
The LeaderKing Dedede
The LancerKirby
The Smart GuyNess
The Big GuyBowser
The ChickLuigi
Sixth RangerSonic the Hedgehog

Syphon Filter: The Omega Strain
The LeaderCobra
The LancerGabe Logan
The Big GuyGary Stoneman
The Smart GuyTeresa Lipan
The ChickLian Xing
The MentorImani Gray
The Sixth RangerLawrence Mujari