Most Popular Rip Van Winkle Movies and TV Shows

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1. The New Misadventures of Ichabod Crane (1979 TV Movie)

30 min | Animation, Family

7.6
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    1 2 3 4 5 6 7 8 9 10 7.6/10 X  

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

4.4
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    1 2 3 4 5 6 7 8 9 10 4.4/10 X  

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

4.5
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    1 2 3 4 5 6 7 8 9 10 4.5/10 X  

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

5.9
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    1 2 3 4 5 6 7 8 9 10 5.9/10 X  

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

6.1
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    1 2 3 4 5 6 7 8 9 10 6.1/10 X  

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

4.5
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    1 2 3 4 5 6 7 8 9 10 4.5/10 X  

"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

4.4
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    1 2 3 4 5 6 7 8 9 10 4.4/10 X  

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

4.4
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    1 2 3 4 5 6 7 8 9 10 4.4/10 X  

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

4.5
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    1 2 3 4 5 6 7 8 9 10 4.5/10 X  

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

4.4
Rate this
    1 2 3 4 5 6 7 8 9 10 4.4/10 X  

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

4.6
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    1 2 3 4 5 6 7 8 9 10 4.6/10 X  

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Director: William K.L. Dickson | Star: Joseph Jefferson

Votes: 403

12. Good Little Monkeys (1935)

Approved | 8 min | Animation, Comedy, Short

6.4
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    1 2 3 4 5 6 7 8 9 10 6.4/10 X  

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

Rate this
    1 2 3 4 5 6 7 8 9 10 -/10 X  

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

9.1
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    1 2 3 4 5 6 7 8 9 10 9.1/10 X  

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



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