James Whitcomb Riley deserves some of the credit for what came downstream of his pen. If you don’t know his name, it’s because time and fashion erode even the most popular artists from memory. Riley (1849-1916) was chiefly a poet, well-known in his time, and especially famous in Indiana, and maintains lingering fame there. Riley wrote much of his stuff in dialect reflective of that part of America, and much of his work was poetry aimed at children. This is the guy who took the African-American folksong “Shortnin’ Bread” and published a version of it as a poem. Riley was sufficiently famous, for a “rural poet”, to share stages with Samuel Clemens, at least until Clemens complained that Riley was upstaging him. He also hung out with fellow Hoosier Lew Wallace (Ben Hur). Riley’s folksy poetry, served up in nostalgic dialect, was a popular balm during a period of industrialization, harking back to an earlier time.
One of Riley’s most famous works was a poem called “Little Orphant Annie” (aka “The Elf Child”, 1885) - in which the eponymous orphan warns other children that misbehavior will make them the target of kidnapping by goblins. Yes, really. The poem was based on an orphan girl who worked for Riley’s family; he also wrote “The Raggedy Man” based on a hobo-type who worked for his father. “Little Orphant Annie” inspires both Raggedy Ann and (the title of) Little Orphan Annie. Perhaps we’ll talk about Little Orphan Annie (leapin’ lizards!) in another installment.
Johnny Gruelle, an illustrator and cartoonist, was family friends with James Whitcomb Riley. He created Raggedy Ann (1915) and Andy (1916), and based Raggedy Ann’s name on the two aforementioned poems, with which he was very familiar. Raggedy Ann is a strong entry in the “toys come to life” subgenre of children’s (nursery?) fantasy. She’s an old rag doll who has adventures when her owner isn’t around. This trope is of considerable vintage, despite what Buzz Lightyear stans might tell you.
Toys coming to life isn’t even new in 1915 when Raggedy Ann appears - after all, there was Hoffman’s (and Dumas’) Nutcracker that everybody knew about, and more...
Collodi’s Pinocchio (1881, 1898 for the American edition which Guelle no doubt knew) gave us a marionette who wanted to be a real boy. This tale is sufficiently influential that we can credit Astro Boy and a thousand other robots-desiring-humanity to it, including Star Trek’s Data. Have you ever actually read the original Adventures of Pinocchio? There’s so much more to it than the Disney version (which is what you would’ve guessed, surely). Even a quick skim of the Wikipedia article will show the differences (you had me at ‘undertaker rabbits’). And hey, don't forget that 2e Ravenloft adventure The Created stars an evil version of Pinocchio called "Maligno the Carrionette".
Aleksey Tolstoy (distant relation to Leo) did a Russian pastiche or rewrite of Pinocchio; I’d never heard of it, or him, until I started poking around for this post. Aleksey Tolstoy, writing in the 1920s, is still today a celebrated science fiction writer in Russia, and his work The Garin Death Ray is apparently credited by the inventor of the laser with specifically giving him the idea. His novel Aelita involves going to Mars and finding an subterranean Atlantean civilization; since he’s a Burroughs contemporary, I can’t help but wonder what it’s like.
Much of Baum’s Oz oeuvre existed at that time, including the Gump (1904) and Scraps the Patchwork Girl (1913, certainly bearing a stronger resemblance to Raggedy Ann than the Gump does!). And the production team behind the very successful stage adaptation of Wizard of Oz aimed for a repeat by staging Babes In Toyland (1903), telling a fairy tale about animate toys and, interestingly, including a dance number entitled “My Rag Doll Girl”. Note that Babes In Toyland and its several film adaptations feature Little Bo Peep as a character. Take that, Lightyear! And don’t forget Parade of the Tin Soldiers (1897), a fine little march often performed in popular revues - including the famous Rockettes’ Christmas Show for decades.
The animated/living toy does seem to develop into a robust subgenre in the 20th century. Margery Williams’ The Velveteen Rabbit was published in 1922, featuring a stuffed rabbit that hoped to become real, if only its owner would love it enough. The Velveteen Rabbit has that scary scarlet fever bit and a bittersweet ending that seems to make it more in line with a Hans Christian Andersen story than what would become the standard “animated toys” romp of the 20th century. Note that Margery Williams cited Walter de la Mare as her inspiration for writing children’s literature. Also, Williams wrote a werewolf horror story ‘The Thing In The Woods’ which H. P. Lovecraft read and commented on - and may have helped inspire The Dunwich Horror. Lovecraft also liked Walter de la Mare’s ghost stories. I’m not much into horror myself, but I look forward to reading de la Mare’s forgotten fairy-story fantasy like The Three Mulla Mulgars, which sees a trio of monkeys grapple with a magic amulet. Much more my speed. Watership Down uses some de la Mare quotes in it, so we’re back to fantasy rabbits again there...
Thomas Disch’s Brave Little Toaster (1980) stars small appliances rather than toys, but has a similar “animated objects and their relationship with their owner/master” setup. It’s also basically The Incredible Journey (1961) - there are no new ideas, perhaps, only novel and amusing permutations and recombinations. Keep in mind that although, thanks to the animated movie, you may think of The Brave Little Toaster as a children’s story, it’s only a children’s story in form of presentation and structure - there’s a lot of humor and thoughtful stuff for grown-ups in there, and the novella itself was nominated for a number of fantasy & science-fiction awards. When the novella first appeared in a magazine, it had cover art from Gahan Wilson, for crying out loud. But of course Thomas Disch is best known as a New Wave science-fiction author in the first place, so maybe Toaster is his most kid-friendly work anyhow.
That seminal year 1980 also brings us The Indian In The Cupboard, featuring more toys come to life. Lynne Reid Banks’ previous novel, The Farthest-Away Mountain, is a more straightforward fairy-story type fantasy with gargoyles and gnomes in it - I look forward to finding a copy. Despite the Indian in the Cupboard and its sequels being bestsellers with a deepening fantasy (and time-travel) mythology - and a major motion picture to boot - the books have recently fallen out of fashion since the Native Americans in the books are portrayed as cultural caricatures. Again, though, a movie puts the living toy gimmick back in the water. 80s kids were aware it was a thing. The later film Small Soldiers only sort-of counts, since those action figures aren’t coming to life magically.
John Lasseter liked The Brave Little Toaster and wanted to do a film of it, but ended up doing Toy Story instead. More on that saga here; that article will also reveal to you the connection between The Brave Little Toaster and Saturday Night Live.
Enough picaresque meandering! Back to Raggedy Ann!
Although a good portion of the Raggedy books deal with more mundane living-toy adventures (the challenge of losing one’s stuffing, for example), they also contain all manner of fantasy-influenced adventures. There are fairies right from the first book, and later witches, enchanted items, strange faraway lands, and wishes-come-true. There is (light) peril, and there are occasional rescues to perform. The first two books, Raggedy Ann and Raggedy Andy, are out of copyright - you can find them via Gutenberg, LibriVox, etc. Gruelle’s fantasy The Magical Land of Noom, in which children build a flying-machine and meet the fantastic inhabitants of the Moon, is also at Project Gutenberg.
Raggedy Ann and Andy had renewed presence after 1977’s animated film RA&A’s Musical Adventure, featuring music from Joe Raposo of Sesame Street fame. The movie’s lead animator was Richard Williams, whose legendary work I guarantee you’ve seen (click through and stare in wonder at all the stuff he’s touched, including Who Framed Roger Rabbit). In the film, Raggedy Ann was voiced by Didi Conn, who later hung out at Shining Time Station with a bunch of talking trains, so maybe animating the inanimate is a thing she’s into - I expect I’ll talk about The Railway Series another time. The ‘Musical Adventure’ is bizarrely not streaming (way to drop the ball, Paramount) but exists on YouTube because of course it does. I recommend checking it out; the central storyline is nonexistent, but there are a boatload of weird characters you could drop into your D&D game (once given weaponry, of course).