The story has been adapted for other media for the last two centuries, from stage plays to an operetta to cartoons to films.
Actor Joseph Jefferson was most associated with the character on the 19th-century stage and made a series of short films in 1896 recreating scenes from his stage adaptation, and which are collectively in the U.S. National Film Registry. Jefferson's son, Thomas, followed in his father's footsteps and played the character in a number of early 20th-century films.
Composer Ferde Grofe spent twenty years working on a symphonic tone poem based on Rip Van Winkle, eventually reworking the material into his Hudson River Suite. One of the movements is entitled "Rip Van Winkle" and is a musical depiction of the story.
The 1960s Tale Spinners For Children record series included a dramatization of the Rip van Winkle story in which the name of Rip's daughter was changed to "Katrina" and the characters of Nicholas Vedder and Derrick Van Bummel were given more importance.
In the 16th episode of The Famous Adventures of Mr. Magoo, which originally aired on January 16, 1965, Mr. Magoo (voiced by Jim Backus) plays Rip Van Winkle.
There is a classic Twilight Zone episode, entitled "The Rip Van Winkle Caper", in which criminals cryogenically freeze themselves to hide for a robbery, and wake up hundred years later.
The story also inspired an episode of The Flintstones entitled "Rip Van Flintstone", which originally aired on November 5, 1965. In it, Fred falls asleep at the Slate Company Picnic and dreams he has awakened in Bedrock twenty years in the future, now a city with a population of 30,000. Besides a change in his personal appearance (Fred has grown a long beard, his hair has turned white and he needs a cane) he first finds out that Slate Company has gone out of business. Fred has been presumed dead and is now alone and forgotten; Barney has become a rich oil tycoon and Wilma has become a bitter old widow. The only one to remember him is his daughter Pebbles, now a full-grown woman who has married Bamm Bamm. Betty is mentioned in the dream sequence but not seen, implying that she has died. At one point during the episode, he even says, "Maybe I have fallen asleep for twenty years like in that Rip Van Winklestone story." However, Fred suddenly wakes up young again, realizing he was only momentarily dreaming.
The story was also parodied in the Laurel and Hardy cartoon series in an episode entitled "Flipped Van Winkles".
A claymation version of the story was produced and directed by Will Vinton in 1978 and was nominated for an Academy Award for Short Subject Animation. The animated film was named Rip Van Winkle.
In the Faerie Tale Theatre children's television series hosted by Shelley Duvall in the 1980s, Francis Ford Coppola directed the episode "Rip Van Winkle" in which actor Harry Dean Stanton played the title role.
A 1988 issues of Boys' Life, with its "Dink & Duff" comic strip has the African-American Cub Scout Dink pondering the meaning of Americanism, only to lapse into a coma and awaken in 2068, although he still has not grown up. He is greeted by a boy who addresses him as "Rip van Dinkle", who tells him that in the 80 years that have passed the United States of America has been defunct and is now the "Royal Dominion of America", or R.D.A., a monarchy under a "King Kongoon". Dink is appalled by the heavy regulations he is now subject to, such as only being allowed to wear the official R.D.A. uniform instead of his Cub Scout uniform or only being allowed to eat vegetables in order to contribute to a "healthy society". Dink is shocked awake back to 1988 realizing it was only a nightmare, but with a better understanding of personal liberty.
Issue 12 of Classics illustrated fleshed out the Rip Van Winkle story with dialogue & incidents. Rip Van Winkle, trying to hunt for food, mistakes the family's last cow for a bear and shoots it. His wife drives him out of the house for that, and orders the children to never speak of their father again. The dwarves make violent threats to Rip, who is then told that the only way to redeem himself is to have a drinking contest with them. The drink puts him to sleep for 20 years.
There is also an episode of the HBO show Happily Ever After: Fairy Tales For Every Child. They retold popular fairy tales by setting them in different cultures and settings and featuring voices provided by celebrities. For Rip Van Winkle they did a Feminist retelling of the story, given a 1960s twist, and told from the point of view of Rip's wife Vanna.
The TV show Wishbone showed the dog imagining himself as the title character, complete with the men playing ninepins and his mistaking the George Washington Inn for his old hangout of the King George Inn. It is set against the family meeting an elderly black woman who has not lived in her town since childhood, and her remarking at the change since her return makes her feel akin to Rip van Winkle.
In 2014, the web series Classic Alice adapted Rip van Winkle for four episodes. The titular character cuts class to recreate van Winkle's nap and finds she missed too much to catch up on, which makes her feel quite like Rip.