Most Popular Rip Van Winkle Movies and TV Shows
1. The New Misadventures of Ichabod Crane (1979 TV Movie)
30 min | Animation, Family
Sleepy Hollow, a town plagued by the Headless Horseman, hires the most educated person they can find to fight him - Ichabod Crane. He, talking horse and dog, and Rip van Winkle go on the quest. But the Horseman has a secret.
Director: Vic Atkinson | Stars: Kreskin, Pat Buttram, George Lindsey, Larry D. Mann
Votes: 19
2. Rip Leaving Sleepy Hollow (1896)
Not Rated | 1 min | Drama, Short
A series of short black and white films from director William K.L. Dickson which chronicle the adventures of Rip Van Winkle.
Director: William K.L. Dickson | Star: Joseph Jefferson
Votes: 409
3. Rip's Toast to Hudson (1896)
Not Rated | 1 min | Short, Fantasy
A series of short black and white films from director William K.L. Dickson which chronicle the adventures of Rip Van Winkle.
Director: William K.L. Dickson | Star: Joseph Jefferson
Votes: 404
4. One for the Book (1940)
Approved | 18 min | Short, Comedy, Fantasy
On a desktop with many books, familiar characters in literature (such as Captain Kidd, Huckleberry Finn, Robinson Crusoe, and Rip Van Winkle) come out of their books after dark. When the ... See full summary »
Director: Roy Mack | Stars: Betty Hutton, Hal Sherman, Miriam Grahame, Beaus & Belles
Votes: 68
5. The Legend of Rip Van Winkle (1905)
Not Rated | 10 min | Short, Drama, Fantasy
Pioneer filmmaker Georges Melies tells his version of the famous Washington Irving story of a man who takes a nap and wakes up 20 years later.
Director: Georges Méliès | Stars: André Méliès, Georges Méliès
Votes: 169
6. Rip's Toast (1896)
Not Rated | 1 min | Drama, Short
"Here the celebrated actor Joseph Jefferson is shown giving his famous toast. Mr. Jefferson's features distinctly show on this picture that by watching the motion of his lips one could ... See full summary »
Director: William K.L. Dickson | Star: Joseph Jefferson
Votes: 417
7. Rip's Twenty Years' Sleep (1896)
Not Rated | | Drama, Short
A series of short black and white films from director William K.L. Dickson which chronicle the adventures of Rip Van Winkle.
Director: William K.L. Dickson | Star: Joseph Jefferson
Votes: 422
8. Awakening of Rip (1896)
Not Rated | | Drama, Short
A series of short black and white films from director William K.L. Dickson which chronicle the adventures of Rip Van Winkle.
Director: William K.L. Dickson | Star: Joseph Jefferson
Votes: 456
9. Exit of Rip and the Dwarf (1896)
Not Rated | 1 min | Drama, Short
A series of short black and white films from director William K.L. Dickson which chronicle the adventures of Rip Van Winkle.
Director: William K.L. Dickson | Star: Joseph Jefferson
Votes: 398
10. Rip Passing Over the Mountain (1896)
Not Rated | 1 min | Short, Fantasy
A series of short black and white films from director William K.L. Dickson which chronicle the adventures of Rip Van Winkle.
Director: William K.L. Dickson | Star: Joseph Jefferson
Votes: 408
11. Rip Meeting the Dwarf (1896)
Not Rated | 1 min | Short, Fantasy
Director: William K.L. Dickson | Star: Joseph Jefferson
Votes: 403
12. Good Little Monkeys (1935)
Approved | 8 min | Animation, Comedy, Short
The Devil comes out of Dante's Inferno, hoping to get the See No Evil, Speak No Evil and Hear No Evil monkeys to his side, but a bunch of literary characters come to the rescue of the monkeys.
Director: Hugh Harman | Star: The Rhythmettes
Votes: 54
13. Summer Daze (1932)
18 min | Short, Comedy
Karl's so lethargic and sleepy, he dozes off at his club, and nobody notices him for days. To give him some pep, George takes him and their wives camping in the Adirondacks, but Karl still ... See full summary »
Director: Albert Ray | Stars: George K. Arthur, Karl Dane, Aileen Cook, Marjorie Beebe
14.
Wishbone (1995–1998)
Episode:
Digging Up the Past
(1995)
TV-Y7 | Adventure, Comedy, Family
Joe, Ellen and Wishbone meet a woman who lived in their home over 40 years ago, who comes to see the house and find the treasures she left behind as a kid. Wishbone imagines himself as Rip ... See full summary »
Stars: Larry Brantley, Jordan Wall, Christie Abbott, Adam Springfield
Votes: 11