The Legend of Zelda: Hyrule Warriors

[Jermungandr]

Okay let me think ...

Heroes
Game Boy Generation:
- Ralph (OoA)
- Maple (OoA/OoS)
- Din (OoS)
N64 Generation:
- Darunia or Darmani (OoT/MM)
- Ruto or Mikau (OoT/MM)
- Great Fairy (OoT/MM)
- Nabooru (OoT)
Toon Generation:
- Tetra (WW/PH)
- Medli or Komali (WW)
- Tingle (most)
- Orca (WW)
- Linebeck (PH/ST) (hey if they can come up with a moveset for Agitha he should be easy)
Wii Generation:
- Groose (SS)
- Telma (TP)
"Link Between" Series:
- Ravio (LBW)
- Queen Oren (LBW) (aka the only LBW sage I found interesting)


Villains
Game Boy Generation:
- Onox (OoS)
- Veran (OoA)
N64 Generation:
- Ganondorf (OoT)
- Skull Kid (MM)
- Twinrova (OoT/OoS/OoA)
Toon Generation:
- Vaati (MC)
- Byrne (ST)
- Phantom Ganon (most)
Wii Generation:
- Ghirahim (SS)
- Zant (TP)
"Link Between" Series:
- Yuga (LBW)
- Agahnim (LttP)
- Ganon (LttP)

As much as Link's Awakening is one of my favorite games in the franchise, I couldn't really come up with any characters from it that really represent either faction very well.

Rick, Dimitri, and Moosh I imagine would make good summon attacks for either Din or Maple.