Quotes / Heads I Win, Tails You Lose

Lynx: "You cannot defeat me, Serge... This is because denying me is the same as erasing your very existence."
Serge: (beat) "But I just did defeat you. What are you even talking about? You don't even know, do you?"
Lynx: "Foolish young child. You actually believe there is a connection between gameplay and cutscenes. Let me shatter your delusions of grandeur."
— From The Dark Id's Let's Play of Chrono Cross, after the final battle of the first act

Dan: "Heads, I win. Tails, you lose?"
Gavin: "Yeah."
Dan: "You lose."
The Slow Mo Guys on deciding who is shot with a paintball gun

"Failure isn't allowed until it's mandatory."

"Why am I even trying anymore?"
Raiden, Let's Destroy Metal Gear Againnote 

Billy the Kid: What I win, I keep. What you win, I keep.
Bill and Ted: Sounds good, Mr. the Kid!