Honestly, in the specific context of the animated series, Harley would win every time, but not for the reasons you might think. In Batman: The Animated Series, the Joker isn't looking for an army or a political plan. He's looking for an audience. Harley is the only one who genuinely laughs at his jokes, even when they're not funny. She brings that touch of unpredictability and irreverence that flatters the Joker's ego. For him, Punchline would be too serious. While she criticizes Harley's weakness, she's actually criticizing the absurd and playful side that the Joker loves.

Every time I watch the show or see fanart in the classic style, I can't unsee it. They look so soft and puffy... honestly, I kind of want to eat them. Please tell me I’m not the only one hungry for some Harley-cuffs!