Here's one of the earliest comic-strip crossovers I've come across: in this abortive 1922 wedding for Winnie Winkle, her wedding party is attended by other luminaries who shared the same publishing syndicate. I don't know all of them but can place Walt Wallet and Skeezix from GASOLINE ALLEY, THE GUMPS, and HAROLD TEEN and girlfriend (the latter on far right).
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