CSotD: I dreamed I was there, in Crossover Heaven
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At one paper where I worked, this poster hung over my desk for a few years, and the whole story that followed is annoying and foolish, but a search-and-inquiry about its potential market value did bring me into the world of comics fans and thence here. So that was a good thing.
Crossovers were a lot more rare when Mandrake was best man at the Phantom's wedding, but they've become a fairly common thing in recent years.
I think it started with The Great Comics Switcheroonie (or Switcheroo, depending on your source) on April Fool's Day 1997, when Baby Blues creators Jerry Scott and Rick Kirkman induced a bunch of cartoonists to draw each other's cartoons, yielding such gems as Family Circus as done by Dilbert's Scott Adams.
The explanation from the chief perpetrators is here, but their secondary link is dead, so here's another that will show you a sampling of the strips that day. The Wikipedia article contains a full roster of who drew what.
In October of that year, Arlo and Janis featured a series of strips in which Arlo buys a piano from a somewhat familiar looking salesman:






What I particularly liked about this was that, for all the winks to the audience, Johnson never did a "big reveal," nor did he depart from the flavor of his own strip. I suppose there might have been some readers who didn't get it, but … well, maybe on Mars.

When Blondie — the strip, good heavens, not the character herself — turned 75, it was marked by a series of strips leading up to a Sunday, Sept. 4, 2005 party attended by a large group of King Features characters.

Richard Thompson, whose Cul de Sac was at that stage still just a regional strip in the Washington Post, did this Richard's Poor Almanac day-after appraisal of the event.

One of the more graphically fascinating crossovers was – like the Phantom/Mandrake one with which we began – a case of a cartoonist assembling his own cast. Brooke McEldowney enlisted the casts of 9 Chickweed Lane and Pibgorn, and spun them into the Jazz Age for an adaptation of A Midsummer Night's Dream.
He subsequently turned it into a book which is for sale on his site, so I'll only offer a few more samples, but it was beautiful and true to the Bard. He discusses his work in this interview, including that piece.
The most socially significant crossover/switcheroonie event came in 2008, when a group of minority cartoonists pooled their talents to point out the foolish racism of the large number of editors who, having bought a "black comic strip," figure they have punched that ticket, pat themselves on the back and thereafter refuse to look at any other strips with minority characters, regardless of what a particular one might be about.
A sampling:





I'd post some more, but, you know, they pretty much all look alike.
Cinema/Comics Crossover
Okay, this isn't really a comics crossover, but bringing up Boondocks reminded me of one of my favorite arcs of all times, and, given the crossover of space opera/comics fans, I'm gonna count it as one anyway.
This came out in May, 2000, a year after "The Phantom Menace" opened. The wounds had not healed and, since it still makes me laff, perhaps they never will:






Writing today's headline has stuck me with an earworm for the day and, while I could change it and spare you, I'd rather offer
Your moment of crossover zen:


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