Where are we going?
I have to share something, since it not only turned into a running gag throughout the night but also prompted an increasingly rare brainstorming session for me today.
We were visiting last night with our friends Kim and Stephen before going off to what turned out to be a late dinner (Atlanta Fish Market, I had sushi and a huge bowl of steamers). Ben was going to spend the night there (our children have been friends for almost their whole lives). They have a big back deck, and we sat out there, and talked, and sipped two of their killer-delish Cape Codders (with cranberry-raspberry juice and mandarin orange vodka – mmm).
I will not be able to convey exactly why this became so very funny. It stands by itself, but for me much of the hilarity – and charm – flowed from the manner of Kim’s delivery. I will always see her face and hear her voice in my mind’s eye when I think of this.
She said that she had seen the funniest bumper sticker ever.
She leaned forward and, with eyes wide, she said:
“Where are we going?”
(pause… beat, beat)
“And why are we in this handbasket?”
Laughter gently roiled up, built, cascaded. Kim’s face looked like it was going to implode. Then both of us burst into uncontrollable, almost hysterical laughter. It may have started out as soft giggling, but it went right into the entire-body-flailing and very rare kind of laughter that feels like a catharsis of the soul.
From then on, it only took “where are we going” for us to start giggling again. John and I continued it later, too.
Thank you Kim! I’ve put that one away as a nugget of gold for when I need a good laugh.
(I’ve made some graphics. Right-click and save, no hotlinking please.)
None of us knew the etymology of the phrase “hell in a handbasket,” and I couldn’t stop speculating about it. It’s really a very odd idiomatic phrase. It rolls with the alliterative ease that its content suggests, so it’s one of those examples of textured language that I always love.
My own brainstorming came up with this:
Since it generalizes from the specific onto a widespread and or/universal diagnosis, it works as as shorthand/catch-all diagnosis. It is a very curmudgeonly phrase, associated more with older, conservative people than with the young. To me, it signals a lack of flexibility with respect to cultural change. The “hell” part is self-explanatory.
There is a sense of ease in the “being carried” – not unlike the “slippery slope” metaphor – and the pace seems fast. The “going” has already been in progress for a while, and the speed is increasing. We’re already past the point where stopping would be possible.
It is never a command (“you go to hell in a handbasket”), but always a description of perceived conditions (“this country is going to hell in a handbasket”). 
Although it is a reactive statement, it also functions as an implicit critique of passivity with regard to the condition being criticized.
There is a cognitive dissonance for me in the visual image of a handbasket.
A handbasket – a small basket with a handle – is something that is typically used for gathering flowers, or berries, or garden veggies, or Easter eggs. I imagine a very carefree, happy little girl, carrying something through the woods – like Little Red Riding Hood? 
One of the things that made the bumper sticker amusing was the idea of a wide-eyed someone asking the “carrier” where they were going. The context of the bumper sticker suggested the automobile as the conveyor, so it was a surprise to have it switched out for the handbasket. Then there was also the implication of children asking “where are we going?,” like “are we there yet?”. Multiple surprises.
Moving on. What would be of an appropriate size to be conveyed to hell in a handbasket?
A baby, like baby Moses being carried down the Nile? (Do you remember that weird song “There’s something in the bag – Mommy, Mommy?”?) Some human parts? The heart, the head, the hands?
Or, looking at the other end of the scale problem, perhaps the being doing the carrying is… very large?
Another interesting consequence of the passive construction is that agency is completely unspecified. Who is carrying the handbasket? That’s an interesting question. I have no answer.
So, what – something or someone – a huge demon, perhaps – is skipping through the woods, conveying “this world” or “this country” to hell – in a handbasket? 
One of the gods – or goddesses? The more you think about it, the stranger it is. The scale is all off (at least for Western thought, it is).
So then I went to search. There’s not really that much hard evidence on the etymology – but post if you’re aware of anything else of interest.
Clues to the origin of “going to hell in a handbasket,” meaning “deteriorating rapidly or utterly,” are, unfortunately, scarce as hens’ teeth. The eminent slang historian Eric Partridge, in his “Dictionary of Catchphrases,” dates the term to the early 1920’s. Christine Ammer, in her “Have A Nice Day — No Problem,” a dictionary of cliches, agrees that the phrase probably dates to the early 20th century, and notes that the alliteration of “hell” and “handbasket” probably contributed to the popularity of the saying. Ms. Ammer goes a bit further and ventures that, since handbaskets are “light and easily conveyed,” the term “means going to hell easily and rapidly.” That seems a bit of a stretch to me, but I do think the addition of “in a handbasket” (or “in a bucket,” as one variant puts it) does sound more dire and hopeless than simply “going to hell.”
This phrase, meaning “to deteriorate rapidly”, originated in the U.S. in the early 20th century. A handbasket is just a basket with a handle. Something carried in a handbasket goes wherever it’s going without much resistance.
James L. Rader of Merriam-Webster Editorial Dept. writes: “The Dictionary of American Regional English […] records ‘to go to heaven in a handbasket’ much earlier than […] ‘hell,’ which is not attested before the 1950s. The earliest cite in our files is from 1949 […]. ‘In a handbasket’ seems to imply ease and and speed […]. Perhaps part of the success of these phrases must simply be ascribed to the force of alliteration. DARE has a much earlier citation for another alliterative collocation with ‘handbasket’ (1714), from Samuel Sewall’s diary: ‘A committee brought in something about Piscataqua. Govr said he would give his head in a Handbasket as soon as he would pass it.’ I suspect that ‘to go to hell in a handbasket’ has been around much longer than our records would seem to indicate.”
I would think that the metaphor would be more directional, more path-oriented. “Going to hell in a handbasket” implies that we are going the wrong way. It’s not under our own steam, as it were, but simply being carried along by…something…a larger agency or force. I guess that’s the danger in “going with the flow.”
So the timeline goes from “head in a handbasket” to “heaven in a handbasket” to “hell in a handbasket”… hmm.
I wonder if the history of the phrase had anything to do with beheading… I know that there was a basket to catch the head as it fell off from the stage of the guillotine. Before that, swords were used. Beheading is a quick way to the afterworld. No-one seems to have made this connection. I wonder.
Here’s another thought, the most literal: “Hand Basket” = a basket full of hands. The possibility certainly haunts the shadowy corridors of interpretation. “Handbasket” is an unusual word, somehow. Thieves’ hands, perhaps? I wonder how far back this expression really might go.
I’m not sure how the meaning of “deterioration” would have come into it, exactly, unless someone actually was carrying around a head, or a basket of severed hands – in a hot climate. And who carries them? And how quickly? Hmmm.
What happens to the heads or hands? Would they have been burned, by any chance? City dump, fiery pit, anything like that?