Sam & Max would win this hands-down. It's one thing to see two characters working together, but you don't really understand the depths of their relationship until they're separated. And as evidenced in various episodes/mediums, Sam tends to become violent and manic depressive in the absence of Max - and Max will just sit there screaming to himself in the absence of Sam. Each has a chaotic nature that keeps the other in check.
Sybil Pandemic got it completely right back in Season 1 when she let Sam & Max use her dating service and she automatically paired them up together as the perfect couple.
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