Here Are the Best Charlie Brown Movies to Watch This Holiday Season

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Everett

In terms of timeless movies, nothing quite compares to those of Charlie Brown. First introduced to the public as a comic strip in 1947, the lovable and quirky Charlie Brown has become a common household favorite over the years, with several movies and TV specials considered by many to be quintessential American classics. Perfect for holiday traditions or indulging in some feel-good relaxation time, Charlie Brown and his group of friends always rise to the occasion with silly antics and heartfelt messages that anyone can enjoy, regardless of age. Since Charlie Brown's first TV debut in 1965, there have been several follow-up movies, TV specials, and spinoffs, but which are the best ones worth watching? Will It's the Great Pumpkin, Charlie Brown or A Charlie Brown Christmas take the top spot — or will it be an under-the-radar movie? Read on to find out which Charlie Brown film outranks the rest.

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A Boy Named Charlie Brown
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A Boy Named Charlie Brown

The film that started it all. In his feature-film debut, we are introduced to Charlie Brown, a meek yet kind boy, as he starts his first baseball game of the Little League season. This movie is responsible for establishing Charlie Brown's character, as well as giving the audience a look into his life and cherished friends including Lucy, Patty, Pig-Pen, Linus, Sally, and more. Though it has a special place in history, A Boy Named Charlie Brown doesn't hold the same weight as the later TV specials.

Watch A Boy Named Charlie Brown on Hulu.

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It's a Mystery, Charlie Brown
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It's a Mystery, Charlie Brown

The Peanuts gang are all under investigation in It's a Mystery, Charlie Brown. When a rainstorm blows away Woodstock's bird nest, Woodstock enlists the help of Snoopy to find it. Taking on the persona of Sherlock Holmes, Snoopy goes door to door asking Charlie Brown and his friends hard-hitting questions regarding the nest. With playful wit and charm, It's a Mystery, Charlie Brown is bound to make you laugh.

Buy the It's a Mystery, Charlie Brown DVD on Amazon.

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Charlie Brown's All Stars
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Charlie Brown's All Stars

Following the success of A Charlie Brown Christmas, Charlie Brown's All Stars joins Charlie Brown and his friends as they are fighting to win in Little League. After a devastating loss in his first game of the season, Charlie Brown struggles when he has to make a decision between his friends and the sport he loves to play. Though this special is less popular than some of the other Charlie Brown titles, it is a valuable and timeless lesson about friendship, loyalty, and integrity.

Buy the Charlie Brown's All Stars DVD on Amazon.

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It's Christmastime Again, Charlie Brown
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It's Christmastime Again, Charlie Brown

Airing nearly 30 years after the original Charlie Brown Christmas special, It's Christmastime Again, Charlie Brown gives viewers the nostalgia from the classic with a modernized twist. Released in 1992, the special has several different storylines that all revolve around Christmas, including Snoopy dressing up as Santa, Charlie Brown selling wreaths, and a musical snowman (that is just Woodstock in disguise). The magic in a Charlie Brown Christmas special is unparalleled, which is why this falls on the list of the most beloved movies.

Watch It's Christmastime Again, Charlie Brown on Amazon Prime Video.

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Happy New Year, Charlie Brown
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Happy New Year, Charlie Brown

As Christmas break is quickly approaching, Charlie Brown and friends are excited to make plans. Unfortunately, those plans are cut short by a mean teacher's last-minute assignment. Over Christmas vacation, Charlie Brown is plagued with reading and writing a book report on Leo Tolstoy's War and Peace. Throughout the special, Charlie Brown finds crafty ways to get out of the boring assignment while making plans for New Year's Eve. The frustrations and stress of completing work over a holiday break are universally felt, making this a timeless classic.

Watch Happy New Year, Charlie Brown on PBS and Apple TV+.

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Be My Valentine, Charlie Brown
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Be My Valentine, Charlie Brown

Love is what makes the world go 'round. In this Charlie Brown special, love is in the air as Valentine's Day preparations are underway. The special centers on Charlie Brown and his friends as they fill out valentines for everyone at school. Anticipating that he will receive an influx of valentines, he brings a briefcase to school, only to get a single candy heart with a nasty message on it. This bummer for Charlie Brown can be a nice moment of commiseration for you, as a little Valentine's Day disappointment is something most people have experienced.

Watch Be My Valentine, Charlie Brown on PBS and Apple TV+.

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The Mayflower Voyagers (This Is America, Charlie Brown)
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The Mayflower Voyagers (This Is America, Charlie Brown)

Often watched as an accompaniment to A Charlie Brown Thanksgiving, The Mayflower Voyagers tells the story of the Mayflower and the pilgrims arriving to America. In the special, Charlie Brown and his friends ride on the Mayflower with the pilgrims but run into some trouble when a powerful storm hits. In the end, all on board the Mayflower make it across the ocean safely. Combining a little history with the lighthearted nature of Charlie Brown and wrapping it around the Thanksgiving holiday places this special in the top five list.

Watch The Mayflower Voyagers on PBS.

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A Charlie Brown Thanksgiving
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A Charlie Brown Thanksgiving

Comforting, heartwarming, and laugh-out-loud humorous at points, A Charlie Brown Thanksgiving is a special that can't be missed on Thanksgiving. As the gang prepare to go to Grandmother's house for Thanksgiving dinner, Peppermint Patty intervenes and hosts dinner at her house. Enlisting the help of Snoopy and Woodstock, the Thanksgiving meal ends up consisting of buttered toast, jellybeans, pretzel sticks, and popcorn. A stark contrast to what many are familiar with in terms of Thanksgiving dinner, A Charlie Brown Thanksgiving leaves viewers laughing the whole time.

Watch A Charlie Brown Thanksgiving on PBS and Apple TV+.

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It's the Great Pumpkin, Charlie Brown
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It's the Great Pumpkin, Charlie Brown

Rules are rules; you can't have Halloween without the Great Pumpkin. In It's the Great Pumpkin, Charlie Brown, the gang of friends are in full gear preparing for fall and Halloween. There are beautiful autumnal colors, costumes, and trick-or-treating. What else could you want?

Watch It's the Great Pumpkin, Charlie Brown on PBS and Apple TV+.

01
A Charlie Brown Christmas
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A Charlie Brown Christmas

On a cold, wintry day, A Charlie Brown Christmas makes you feel like you are being wrapped in the coziest blanket. The beautiful snowy scenery, the humor of Charlie Brown finding the perfect Christmas tree (only to find the most limp, bare one), the timeless "Christmastime Is Here" and "Hark the Herald Angels Sing" songs, and the message of friendship put this timeless special at number one.

Watch A Charlie Brown Christmas on PBS and Apple TV+.