As the weather in the city gets colder and the end of the year approaches, our collective desire for winter-themed books, movies, and music grows to an all-time high. Here is a collection of holiday media, hand-picked by the editors of Tigertalk, to explore and enjoy over the winter break. So grab a cozy blanket and a cup of hot chocolate, and let’s begin! 

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Ms. McNeely — Christmas at Pee-wee’s Playhouse (1988)

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Christmas at Pee-wee’s Playhouse is a festive comedy special starring the familiar and well-loved Pee-wee Herman as he partakes in many holiday activities. Filled with celebrity appearances and musical performances, Christmas at Pee-wee’s Playhouse is endlessly fun and entertaining.

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With “talking furniture, gaudy decorations, and tin can phones,” Christmas at Pee-wee’s Playhouse is a silly and lighthearted delight.With cameos from Magic Johnson, Oprah Winfrey, Zsa Zsa Gabor, Cher, and more, the show is Ms. McNeely’s favourite holiday special and an excellent watch for those looking for fun over the winter break. 

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Ms. Williams — A Christmas Story (1983)

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Told in a vignette format of short sequences, A Christmas Story follows the adventures and antics of nine-year-old Ralphie Parker over the holiday season in 1940s Indiana. Wishing for a “Red Ryder Carbine Action 200-shot Range Model air rifle” for Christmas, Ralphie spends much of the movie trying to persuade his parents and Santa Claus to buy it for him. Humorous and nostalgic, A Christmas Story shows the importance of dreaming big and determination. 

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In Ms. Williams’ family, watching A Christmas Story is an annual tradition that never gets old. At once “funny yet charming,” the movie looks at the holiday season through a more realistic lens than the run-of-the-mill Christmas movie. With many exterior scenes shot right here, in Toronto, A Christmas Story is a wonderful choice for those seeking humour and holiday merriment over the winter break. 

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Arya — Love the Coopers (2015)

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Love the Coopers is a Christmas drama that follows main characters Sam and Charlotte Cooper’s final Christmas celebration with their family amid lots of drama and personal issues. As chaos and conflict ensues during the dinner, the Coopers relearn the importance of family and connection while remaining emotional, heartfelt, and funny.

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While there have been thousands of Christmas movies made over the years, Love the Coopers is Arya’s favourite. Told from multiple intersecting perspectives, the film manages to balance comedy and coziness with serious topics like divorce, drifting apart, and growing up. A great comfort movie to watch over the winter break, Love the Coopers is filled with “relatable and goofy characters,” including Arya’s personal favourite, Aunt Fishy.

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Lily — Little Women (1994)

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Adapted from Louisa May Alcott’s 1868 classic novel, Little Women is a coming-of-age movie following the lives of four very different sisters: Meg, Jo, Beth, and Amy March. As they navigate growing up in their small town in Massachusetts, the sisters make new friends, fall in love, and experience different life events, learning what family, love, friendship, and womanhood are truly all about.

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There have been several film adaptations of Little Women over the years, and I’ve seen many of them at one point or another. I often hear people talk about their love for Greta Gerwig’s 2019 adaptation of the novel, and while I enjoyed it as well, I’ve always been particularly fond of Gillian Armstrong’s 1994 version. Starring Winona Ryder, Christian Bale, Kirsten Dunst, and Claire Danes, I’ve found that there’s something honestly really magical about this movie—something inherently wintry yet warm. Even if you’ve seen this film before or another adaptation of the story, the 1994 version of Little Women is the perfect treat for those looking for something cozy and familiar to watch over the frigid winter break. 

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Tigertalk Writers

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Finally, here is a curated playlist of winter and holiday-themed songs from the writers of Tigertalk! Happy listening, and enjoy the break, Harbord! 

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