Five Man Band / Web Original

Animated Croft
The LeaderLara
The LancerKurtis
The Big GuyZip
The Smart GuyWinston
The ChickAlister

Cheat Commandos Adventures
The LeaderGunhaver
The LancerFightgar
The Smart GuySilent Rip
The Big GuyCrackotage
The ChickFoxface
Sixth RangerRipberger, Reinforcements, and the Topplegangers
Team PetFirebert
Big GoodFlashfight
Sixth Ranger TraitorReynold/Scrawnjob

Doraleous And Associates
The LeaderDoraleous
The LancersNeebs and Walken (the latter of whom is sometimes The Smart Guy)
The Big GuyBroof
The Smart GuyMirdon
The ChickDrak
Tag Along KidHarry Pooter

Greek Ninja
The LeaderSasha
The LancerDaichi
The Smart GuyDawson
The Big GuyMenelaos
The ChickEleonora

Happy Tree Friends
The HeroCuddles
The LancerToothy, Flippy, and Flaky
The Smart GuySniffles and Handy
The Big GuyLumpy, Nutty, Disco Bear, and The Mole
The ChickGiggles and Petunia
Team DadPop
Tagalong KidCub
Token Evil TeammateFliqpy, Lifty, Shifty, and (possibly) Lammy
"Kid"Appeal CharacterMime
Sixth RangerSplendid and Russell
Companion CubeMr.Pickles and Cro-Marmot(Literally!)

It's A Mall World
The LeaderDean
The LancerEvan
The Big GuyTracii
The Smart GuyTaylor
The ChickHarper

LoadingReadyRun: In the ninth episode of commodoreHUSTLE, Kate deliberately sets this up with the West Coast Motherlovin' Gs.
The LeaderKate
The LancerJames or "The Fixer"
The Big GuyBill
The Smart GuyJeremy
The ChickMatt (who protests his role as "The Girl")

Oxhorn Short Shorts
The HeroOxhorn
The LancerMortuus
The Big Guy(s)Staghorn, Thunk, Warlord Gorechuck
The Smart Guy(s)Associate Professor Evil, Master of Euphemisms
The Chick(s)Lacy, Hippy Elf
Team Pet(s)Hat, Barnaby, Busco

Red vs. Blue

Blue Team
The LeaderLeonard L. Church
The LancerLavernius Tucker (sometimes The Smart Guy)
The Big GuyMichael J. Caboose
The Smart GuyAllison/Agent "Tex" Texas (sometimes The Lancer)
The ChicksKaikaina "Sister" Grif and Frank "Doc" Dufresne
Team PetsShiela and Tucker Jr.

Red Team
The LeaderSarge
The LancerDexter Grif
The Big GuyLopez the Heavy
The Smart GuyRichard Simmons
The ChickFranklin Donut (Aha-ha-ha!)
Team PetThe Warthog

The Surviving team members at the end of Revelation
The LeaderSarge
The LancerTucker
The Big GuyCaboose
The Smart GuySimmons
The ChickGrif
The Sixth RangerWash

Saturday Morning Watchmen ([1])
The LeaderNite Owl
The LancerRorschach
The Big GuyThe Comedian
The Smart GuyOzymandias
The ChickSilk Specter
Team PetBubastis
Sixth RangerJon/Dr. Manhattan
The LeaderKorey
The LancerLeon
The Big GuyCyrus
The Smart GuyCarlyle
The ChickEdie
Team PetCo-Host 3000

Super Mario Bros. Z
The LeadersMario and Sonic
The LancerShadow
The Big GuyYoshi
The Smart GuyProfessor E. Gadd
The ChickLuigi (though not in terms of ability or power)

Super Stories: The Ultimate Justice Squad
The LeaderThe Captain
The LancerHelaron (Unusually, Helaron is not the squad's official second-in-command, but she's been there the longest and has a lot of respect within the group.)
The Smart GuySeer
The Big GuyLongtooth
The ChickMirror (the Captain's official second-in-command)

Tales of MU
The LeaderMack
The LancerStef
The Big GuyIan
The Smart GuyDee
The ChickAmaranth
Tagalong KidTwo

A Very Potter Musical
The LeaderHarry (He is the Chosen One; he is also an attractive, guitar playing, all around cool guy.)
The LancerDraco (Harry's rival. He hates Harry mainly because Harry is cooler then him and Draco is constantly trying to be cool and failing.)
The Smart GuyHermione (She is the Only Sane Man in the show and is the geekiest.)
The Big GuyRon (He has elements of The Lancer too, especially with his Jerk Ass tendencies in Act 1, but he is very much the muscle of the group.)
The ChickGinny (Harry's Love Interest. She genuinely cares for everyone (even Draco, whom the others can't stand) and inspires Harry when no one else can.)