Based on the notes included as part of "Rip Van Winkle", we know that the narrator is Dietrich Knickerbocker, who is Dutch. If he's anything like the narrator for "Legend of Sleepy Hollow" he is very much biased in favor of the Dutch. (Ichabod Crane is not Dutch, and he basically gets pilloried by the various Dutch residents of Sleepy Hollow). This bias creates a sense, in both stories, of us-versus-them, of community, of team membership.
This is one of the things I want to talk about with someone who studies Irving - is this something commonplace in Irving's work, something that is obvious to those familiar to his full body of work? Will I look like a high schooler if I publish an article discussing this as though it is not obvious?
Within the actual story text, while Rip is in the mountains dilly-dallying, he encounters Henry Hudson's ghostly crew, who are taking a bit of shore leave to frolick and drink and play 9-pin, etc. I don't think the specific game matters much; it's mainly important that they are at their leisure and (here is the key, because I think it's all about the work ethic, with the nature and responsibilities of community to individual and vice versa as a component of that theme) they are away from work. The ghostly rum keg serves that function as well. They are carousing, as sailors are reputed to do when they come to shore. Rip joins them, although he hasn't really earned the need to carouse.
The ship's crew is a great vehicle for the blended theme of work ethic and community - if the crew do not work together, if anyone doesn't do their job, the whole crew could drown. They work together, they play together, they rely on one another because they have taught one another that they can rely on one another. The story presents them as ghosts, out of place; however, really Rip is the one out of place in these scenes.
Hudson's crew, in particular, also helps introduce the crucial motif that time is permeable in this story, of course.
I think we are meant to wonder whether Rip was asleep already even before Hudson's ghostly crew show up. That kind of ambiguity can then leave us to wonder whether he is still asleep when he gets back to his village and learns the outcomes for his family and friends. If he's asleep, by the 19th century we are justified in wondering whether this is a wish-fulfilment dream. Rip wants nothing more than to be able to sit and gossip and do exactly what he wants, and a retiree is not criticized for doing those things.
Whether it is a wish fulfilment dream, or whether instead Rip has just been magicked into a situation he finds congenial, the narrator celebrates for him, all the while doing this maddening Chaucerian thing where he presents abominations and acts like they are accomplishments. For an example from Chaucer, Geffrey, who narrates the Canterbury Tales praises the knight based on having served tours of duty on a privateer ship, which is basically thinly veiled piracy. He also praises the knight for having killed many rivals during jousts, which is akin to praising a football for crippling the opposing quarterback.
In "Rip Van Winkle," Rip's daughter is married to one of the urchins that used to follow Rip around in the before times. An urchin is not a well off person, so the daughter's family are probably not well off. Nevertheless, she has to employ her lay-about brother (who takes after Rip, which the narrator seems to think is JUST GREAT), and now she also has to put her father up and feed him, and we can say in advance that he won't be contributing to the coffers in any meaningful way.
Meanwhile, Rip's wife has died from what sounds like an aneurysm or a stroke, probably (paraphrasing) while shouting at some poor fellow about his work habits. And again, the narrator spins this tragic outcome as something worth celebration, because it means Rip is out from under her harpy thumb.
I don't think ultimately that it matters whether he is asleep or whether some magic has befallen him and he is awake and literal time has passed. For my money, what matters is the opportunity for us to think about it. If the sleeping frame is complete (that is, if he actually sleeps for 20 years and actually wakes up a for-real generation later) there's precedent for that sort of bleeding between dream and waking in Piers Plowman. If the sleeping frame is incomplete (that is, if he falls asleep and the whole thing is a dream and we never see him awaken at all), there's some precedent for that, too, still in Piers Plowman.
Hawthorne also uses a similar sort of ambiguity in "Young Goodman Brown" in that penultimate passage where Hawthorne's narrator dismisses the significance of the question - whether it was a dream or not, Brown grew old and bitter and died friendless because of his attitude and behavior, a burden on his family and his community, all of whom he considered damned based on what he saw/dreamed in the forest.
In the end, I think "Rip van Winkle" is exploring the importance of a strong work ethic, and I think he's doing it satirically: By presenting a tragedy through the eyes of a narrator so unreliable that he describes it as romance, Irving creates (for me, anyhow) a very dark, dry humor that 21st century readers might miss completely. To be honest, I find it pretty unsettling, myself.
The satirical target seems to be the idea that the community can afford to support those who refuse to contribute, can tolerate morbid laziness - hearkening back again to Piers Plowman, that a community can afford to tolerate sloth. The argument seems to be that pretending sloth is ok is the same as claiming (as Dietrich Knickerbocker seems to do) that tragedy is to be celebrated, may even lead directly to tragedy.
Does any of this track for you?
