One of the many challenges in working as a comic strip artist is the daily grind of it. Although things have changed enough in recent years so that it's no longer mandatory per se, but the general rule is that they have to churn out a new strip seven days a week, fifty-two weeks a year. A new strip with a new idea every single day. That's no easy task. So when someone comes along to work two strips...? Well, that is certainly an impressive feat.
I think the first person I recall seeing do that was Jim Davis. He had been doing Garfield for several years, and then introduced U.S.Acres. He no longer does both strips, and only does some of the work on Garfield any more however. Of course, he wasn't the first or last to try multiple strips and you could argue he wasn't very successful at it since his second strip only lasted three years. (At that point, I'm not sure how many assistants Davis might have been using, or if he was still trying to do it all himself.)
You've also got team-up efforts that would seem to make the increased workload of a second strip more mangeable. Mort Walker (who was already working on Beetle Bailey) collaborated with Dik Brown (already working on Hagar the Horrible) to develop Hi and Lois together. Tom Batiuk (after working on Funky Winkerbean) launched John Darling with Tom Armstrong and later Crankshaft with Chuck Ayers.
Another alternative is to not make the second strip a seven-day-a-week thing. Greg Cravens has been working on The Buckets for several years, and more recently launched the five-days-a-week webcomic Hubris. Mike Peters does Mother Goose & Grimm every day, but his editorial cartoons are only twice a week.
Well, I haven't done an exhaustive analysis, but I'm currently putting my money on Winsor McCay. His first strips were published in 1903. He tried a couple different titles, but they didn't last very long. His first real success was Little Sammy Sneeze which debuted in July 1904. While still working on that, he launched Dream of a Rarebit Fiend in September of that year. In January 1905, he began The Story of Hungry Henrietta (not one of his more popular strips) and in June, he started A Pilgrim's Progress By Mister Bunion before finally getting to Little Nemo in Slumberland in October. The only strip McCay dropped during this timeframe was Hungry Henrietta so at the tail end of 1905, he was working on four different strips simultaneously. He continued that throughout 1906 before dropping Sammy Sneeze (so he could do a 4,000 cell animation by himself) but he continued on with the other three strips through 1910.
Now, granted, these weren't all daily strips, but they were more detailed and considerably larger than anything you'd find today (often taking up a full newspaper page by themselves). Other earlier cartoonists certainly worked on multiple strips in a serial nature, but does anyone know of any cartoonists working multiple strips simulatenously?
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