Jump to: Spoilers (3)
Director Clea DuVall wrote the film as an autobiography. She has said that she wrote it so she could see her own experiences play out on screen.
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Marks the screenwriting debut of Mary Holland, who also portrays Jane.
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The film is a pioneering holiday-themed romantic comedy centered around a same-sex couple. In fact, the movie features several LGBTQ+ actors including Kristen Stewart, Dan Levy, Victor Garber and Aubrey Plaza. It also is the sophomore film from queer actress/director Clea DuVall.
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Filming took place in Pittsburgh, PA and wrapped in February 2020, just before the film industry was shuttered due to the COVID-19 pandemic.
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One of at least four LGBTQ-related Christmas movies released in 2020. The other three are the made for TV-productions Dashing in December (2020), The Christmas Setup (2020) and The Christmas House (2020). "Happiest Season" was originally set for theatrical distribution and would have been one the first major studio films centered around a female same-sex couple to be released in theaters.
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"Candy Cane Lane" from the opening scene of the film is a real place in Pittsburgh, Pennsylvania. The residents of the street agreed to keep their holiday displays up for a few extra weeks into January 2020 to accommodate the production.
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In an interview on the December 3, 2020 episode of The Late Show with Stephen Colbert (2015), Aubrey Plaza said that after the end of production at the end of February, she asked the man driving her to the airport if she should be worried about COVID-19. He replied that "that s**t's been in Pittsburgh for a long time." She broke the news that Kristen Stewart and several others on the set came down with it, but she didn't.
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While the US theatrical distribution was scrapped due to the pandemic, the movie was released theatrically in select territories, including Hong Kong and New Zealand, while it opened as the #1 movie at the Australian box office.
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Mackenzie Davis trained in ice skating for two months prior to shooting her scenes.
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RuPaul's Drag Race (2009) alumni Jinkx Monsoon (Jinkx Monsoon) and Benjamin Putnam (BenDeLaCreme) are featured in the film.
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First holiday-themed movie by a major studio to have a score by a female composer. The music is by Amie Doherty.
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In Harper's old room there's a poster of Josh Hartnett. The film's director, Clea DuVall, co-starred with Hartnett in The Faculty (1998).
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The production wrap party took place at a haunted house in an amusement park.
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Mary Holland and Clea DuVall first met when they were working on Veep (2012). Although they didn't actually share any scenes, they became firm friends.
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The film was originally intended for theatrical release but with the COVID-19 pandemic affecting the movie exhibition business, Sony opted to sell the U.S. distribution rights to Hulu while retaining the international distribution rights.
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The children's names of Magnus and Matilda is a clear nod to Matilda (1996).
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Alison Brie and Aubrey Plaza both auditioned for the role of Rebecca in Scream 4 (2011). Brie prevailed.
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The convenient store scene was filmed at Love's travel stop in slippery rock PA
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The end credits are accompanied by Instagram snapshots of various episodes in the family's life: Jane's book, Thanksgiving, Ted's election as Mayor, etc. for the following year, through to the next Christmas. This is done in the usual over-the-top, silly manner of social media, with various affixed handles and hashtag missives like "@JaneCaldwell," "proudmom," "#lovemyguy," "#en-gay-ged #lol," etc. One photo shows the twins looking like zombies for their birthday.
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The Oxwood, the gay bar where Abby and Riley have drinks, is a tribute to The Oxwood Inn, a lesbian bar in Los Angeles that closed in 2017. It was the last lesbian bar in Los Angeles at the time of its closing.
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When showing the Instagram posts during the end credits, the photo of the family at a Gay Pride event shows the film's director, Clea DuVall. She has her arm around Aubrey Plaza.
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