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The more I think about it the more I want to see a Terry/Annie crossover. This sort of thing wasn't done in 1940, but the current creative team for Dick Tracy has done several crossovers with defunct News-Tribune strips in recent years -- Annie and her cast have become semi-regulars there, and Tracy even helped them run down Axel when he resurfaced a few years back:
It's also been established that Harold Teen and his friends exist in the current Tracy universe -- still looking and acting like 30s hepcats in the 21st Century:
There have even been brief appearances by an elderly Skeezix Wallet and his even more ancient Uncle Walt. So a Terryverse crossover is long, long overdue. Oh how I'd like to see today's Tracy get a visit from Cheery Blaze, with Annie and company not far behind.
I'm with you as my first choice for a crossover would be T&TP and LOA. Both have well-written complex stories and characters that see the gray in life and play in and highlight it. I think Mary Worth and Dick Tracy together could also be interesting except that MW is written at a higher level than DT.