6 Best Sterling Holloway Movies

By Vlad Zakh · July 8, 2026

Sterling Holloway brought an unmistakably gentle, high-pitched voice to Hollywood over seven decades and is immortalised as the original voice of Winnie the Pooh. The Many Adventures of Winnie the Pooh and Winnie the Pooh and the Blustery Day share honey-loving adventures in the Hundred Acre Wood, The Jungle Book decides whether a boy raised by wolves returns to civilisation, and The Aristocats finds a family of cats lost in the countryside. Meet John Doe and Remember the Night round out the list.

The Many Adventures of Winnie the Pooh (1977)

IMDb ★ 7.5 RT 100%

A gentle bear and his friends wander through the Hundred Acre Wood chasing honey and adventure.

Directed by John Lounsbery & Wolfgang Reitherman · 1h 14m · Rated G

1 nomination

Where to watch

Stream: Disney Plus · Rent or buy: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home

▶ Trailer Letterboxd

Winnie the Pooh and the Blustery Day (1968)

TMDB ★ 7.3

Sterling Holloway voices the bear of very little brain in this short about his forest friends contending with a windy day.

Directed by Wolfgang Reitherman · 0h 25m

▶ Trailer Letterboxd

The Aristocats (1970)

TMDB ★ 7.3

A scheming butler abandons a wealthy Parisian cat and her kittens in the countryside to claim their fortune.

Directed by Wolfgang Reitherman · 1h 18m · Rated G

Where to watch

Stream: Disney Plus · Rent or buy: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home

▶ Trailer Letterboxd

The Jungle Book (1967)

TMDB ★ 7.3

Sterling Holloway appears as a boy raised by wolves in the Indian jungle must decide whether to return to civilisation.

Directed by Wolfgang Reitherman · 1h 18m · Rated G

Where to watch

Stream: Disney Plus · Rent or buy: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home

▶ Trailer Letterboxd

Meet John Doe (1941)

TMDB ★ 7.3

A fabricated newspaper hoax about a suicidal everyman spirals into an unstoppable political movement.

Directed by Frank Capra · 2h 03m · Rated NR

Where to watch

Stream: fuboTV, Philo, Brew, MGM Plus, Pure Flix, Fandor Amazon Channel · Rent or buy: Amazon Video, Fandango At Home, FlixFling

▶ Trailer Letterboxd

Remember the Night (1940)

TMDB ★ 7.3

A prosecutor falls for the shoplifter he's set to convict after inviting her home for Christmas.

Directed by Mitchell Leisen · 1h 34m · Rated NR

Where to watch

Rent or buy: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home

▶ Trailer Letterboxd

Streaming availability data from JustWatch, via TMDB. Availability changes often, so check the service before you plan a movie night.

Vlad Zakh

Founder, Movieix

Founder of Movieix. He started the site because most recommendation pages felt like noise. Here, lists are sorted by who's in the film, where it's from and what mood you're in tonight.

6 Best Sterling Holloway Movies

The Many Adventures of Winnie the Pooh (1977)

Winnie the Pooh and the Blustery Day (1968)

The Aristocats (1970)

The Jungle Book (1967)

Meet John Doe (1941)

Remember the Night (1940)

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