This is another item available at "Busted Tees. Thanks again to Jon Proctor for tipping me off to this site. And, hey, if anybody wants to get me this shirt, I'm an XXL. 
This ran in 2007. Since then Mike Peters has quit referring to this technology as On-star, but more accurately as GPS. On-star still exists, of course, but it's still a car-only-based device, at least as far as I know. On-star seems like a rather expensive service to operate. 
It'd be funnier if it was abandoned landmines... funnier in a much more gruesome and tragic kind of way of course. This one is by Andrew Toos.
This is one from August 2009 by Paresh Nath of The Khaleej Times in Dubai. Captures the situation in Afghanistan fairly well, no?
Does it surprise anybody that there'd be a GPS-based joke that'd reference Dorothy and pals, the most lost girl in literature? Or is it simply a surprise that this joke hasn't been done sooner? Thank you Non Sequitur by Wiley Miller!
Redistricting is one of those few fascinating political games that allows geography to take a front seat in politics. This cartoon by Scott Stantis of the Chicago Tribune as the long aftermath of the redistricting events in Texas finally played themselves out. The Republicans in the Texas State legislature gained enough of a majority to try redistricting without waiting around for the 10-year Census. That prompted legal challenges that went to the Supreme Court, which ruled that this was OK. There's been various attempts to reform this redistricting process. Here's some interesting ideas.
This may very well be one of the most famous and enduring editorial cartoons of all time. Drawn by Gilbert Stuart in 1812, It was a critique of the extents to which politicians will go to protect their seats, by manipulating voting districts to include areas predominantly populated by their own supporters. This cartoon is in fact where the term gerrymandering comes from. 
...Except that I think malls may have less longevity than GPS. I dunno, but it just seems like malls are moving out of favor. Sure, there's still an obscene number of them. But the new shopping mega-complexes being built that I've seen are a move away from the giant central mall concept and more towards a giant "marketplace" concept... that actually, to me, looks like nothing more than a glorified strip mall, but they're called "Lifestyle Centers". Whatever. I avoid them all. Actually, my idea for a "shopping center" is this: Use a GIS to match each and every business within a 1-mile radius of each address. Then mail to each address a thing that looks like a mall directory, but it's actually just a map of their neighborhood with all of the shops/businesses color-coded by category "clothing, grocery, hardware, etc.). I wouldn't be surprised if it generated a decent amount of new (and possibly lasting) commerce for local businesses. Enough new tax revenue, anyway, to justify the expense of the venture, I dare say. So any city GIS-ers out there reading this: Consider that a freebie.
This one ran on my birthday in 2008. And it's about one of my favorite cartographic urban legends (BTW, if a legend is hundreds of years old, can it still be described as urban?). That being, of course, that anybody in Columbus' time believed the Earth was flat (nobody did. The roundness of the Earth was well-established thousands of years at least prior to C.C.). I've addressed that falsehood and its origins here. 
This ran on August 18th, 2009, which I believe was in the middle of the Cash for Clunkers. program. But that program isn't getting referenced here. This is actually a bit dated, then, since it references the bailout of the auto industry from several months previous. 
Ah, the joys of the "Great Recession" of the 'naughts! This comic by Bill Schorr ran over the summer. 
