Art has a way of overcoming political barriers. Art Spiegelman is a radical while Harold Gray, who created Little Orphan Annie, was famously right-wing. But in The Daily Beast, Spiegelman pays handsome tribute to Annie (and mentions a series of reprint books I have a hand in). Here’s an excerpt, although Spiegelman’s full comments are worth a look and can be found here:
The blank-eyed orphan was far grittier and moving than the saccharine Annie you know from the damn musical. One of America’s most popular newspaper strips ever (remember newspapers?) started in 1924 in a world chillingly like ours: crawling with cake-eaters, greedy bankers and international con men who exploit the hardscrabble working stiffs Annie hangs with when her “Daddy” isn’t around to protect her.
Spiegelman had earlier discussed Gray’s work in Todd Hignite’s In The Studio, which richly explored the link between contemporary cartoonists and older comics. Here’s what Spiegelman said in an interview with Hignite:
Even though Harold Gray’s politics make him very unlovable, his strip is amazing. What’s interesting about Gray really isn’t his politics, it’s the fact that somehow, despite everything the strip actually accomplishes that essential trick of making these characters seem alive when you’re reading it. There are very few strips that actually get me to drop my guard enough to get a tear in my eye. I don’t know how he does it – the stories are predicatable, stupid… part of it is that it has this intensity of conviction. He believes in it, so he bulies you almost into believing in it because he does.
sans everything 
“…the hardscrabble working stiffs Annie hangs with when her “Daddy” isn’t around to protect her.”
This is the most interesting feature to me. Daddy is frequently absent on business errands that seem to go horribly wrong. This suggests two things:
1) “Daddy” is actually a terrible businessman who takes too many risks and is apparently a serial entrepreneur of the worst sort.
2) “Daddy” is one of the worst, most negligent parents of all time.
It cracks me up the way he’ll leave Annie in a hotel (prepaid for two weeks!) and not show up for a year. Where the hell is child welfare services (who are always portrayed as busy-bodies at best and outright villainous at worst in the strip)?
It is, of course, one of the most pleasurable comic strips of all time, but don’t think too hard about Annie’s family situation–it’s simply bizarre.