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Well, I’m pretty sure there were instances where Mario and Bowser cooperated. But it doesn’t matter, because even if only 2 answers make sense, the joke already works.
I don’t get it.
Riding somebody is a double entendre, often used as sexual innuendo beyond the literal sense of riding, like on a horse.
But where is Bowser a sidekick?
Depending on your definition of ‘sidekick’, these may also count:
There might be more I’m forgetting.
Well, I’m pretty sure there were instances where Mario and Bowser cooperated. But it doesn’t matter, because even if only 2 answers make sense, the joke already works.
Bowsette may not be Nintendo canon, but it sure as hell is fan canon.