Thoughts

ithurtsmybrain has a list of 1000 bizarre, brain hurting pairings and three-somes.

The ones I'm considering:
Marcus Brody/Queen Lillian (Shrek)
Snuffleupagus/Qui-Gon/Romana
Willy Wonka/Lancelot
Percy Weasley/Faith
Cordelia/Leia Organa
Gimli/Ares/Chloe Sullivan
Leia/Zoe
Jack Sparrow/Kaylee
Voldemort/Blanche DuBois
Jordan (Real Genius)/Headless Horseman
Andrew (BtVS)/Satan (Paradise lost)
Giles/Aragorn
Tonnks/Hawkeye
Lilly von Schtupp/Jethro Bodine
Joker/Mal

I gotta be out of my mind.