In the Belle and Sebastian song "I Could Be Dreaming" an extract from "Rip Van Winkle" is read.
The Phish song "The Sloth" contains the line: "Sleeping all day, (Rip Van Winklin')."
The band Ween's second album features a song called "Sketches Of Winkle" that seems to draw on the story for its lyrics.
In the Manga Hellsing, Van Winkle is portrayed as a young woman who uses a long musket that has seemingly magical bullets that follow its target.
The American stoner/doom metal Band Witch has a song called "Rip Van Winkle" on their debut record from 2006.
Doo-Wop Rock 'n Roll trio Shannon and the Clams have a song called "Rip Van Winkle" on their first LP, "Dreams in the Rat House"
David Bromberg's mournful song "Kaatskill Serenade" on How Late'll Ya Play 'Til? tells the story from Rip's point of view.
The country band Alabama's 1982 song "Mountain Music" mentions Rip Van Winkle in association with Tom Sawyer and Huck Finn.
The story of Rip Van Winkle is recounted by way of parable by the title hero of Max Frisch's novel "I'm Not Stiller".
In the long-running NBC television series Law & Order's episode "Brother's Keeper" Rip van Winkle is mentioned by detective Lennie Briscoe. A worker of the driving range where a man was murdered was caught sleeping on the job, to his defence he says he "was just gonna lie down for 5 minutes, take a little nap" to which Briscoe replies "yeah, a regular Rip van Winkle". The confused man asks "who?" to which Briscoe answers "another guy who took a little nap, woke up and didn't know where he was" after which the opening credits appear.
In the Fox television series Bones episode "The Maggots in the Meathead" (Season 6), intern Colin Fisher reveals that while depressed, he slept 20 hours a day for two months. In a later scene he yawns in front of Dr. Hodgins, which prompts Dr. Hodgins to ask if he's okay. Colin Fisher's response is "are you going to ask me that every time I yawn?", to which Dr. Hodgins sarcastically replies: "Possibly. I don't want you to fall asleep again for two months, Van Winkle".
In a deleted scene from the ABC television series Once Upon a Time episode "Nasty Habits" (Season 3), Rumpelstiltskin chases down a man named Mr. Van Winkle to settle a deal with him. Van Winkle pleads mercy, claiming that he overslept, only for Rumpelstiltskin to curse him into a 100-year sleep. He takes a knife from the sleeping man and presents it to Baelfire as a gift.
In another Fox television series, Fringe, in the episode "The Firefly" (Season 3), main character, Olivia Dunham, after returning to her life from an alternate universe, states: "I feel like Rip Van Winkle. Everything is different."
In another Fox television series, Sleepy Hollow, Ichabod Crane (another Washington Irving character) awakens after being asleep for over 200 years.
In the Fox television medical drama series "House", in the episode "Cane and Abel" (Season 3), Cuddy tells House that his last patient woke up like Rip van Winkle after she injected him with the drug.
In the Indian media Rahul Gandhi Congress vice president has been compared to Rip van Winkle after his statement to cancel the ordinance to protect convicted lawmakers has been made, because he was silent like Rip was sleeping, when the debate/war on the issue was going on.
Mashup artist, V the Viper, made an album in 2013 loosely based on the character Rip Van Winkle.
A Rip Van Fish is a sleeping variety of Cheep Cheep found in Super Mario World. If Mario swims too close to a Rip Van Fish, it will awaken and begin to chase Mario.
Captain America tells Bucky he feels like Rip Van Winkle when the two re-meet in Ultimate Avengers.