Christmas Movies

Meet The Hilarious Cast (& Cameos) Of Happiest Season

As everyone knows, the holiday season promptly begins the day after Halloween. This year has definitely felt less festive than most, but with the arrival of the Clea DuVall-directed Happiest Season, it's finally starting to feel somewhat like Christmas.

Happiest Season isn't exactly a quintessential holiday movie or a typical rom-com. The film introduces us to Abby (Kristen Stewart), an openly gay PhD student gearing up to meet her long-term girlfriend's parents — and, if all goes as planned, propose to her on Christmas. But at the last second, she's thrown for a loop when Harper (Mackenzie Davis) mentions she isn't out to her parents. She asks that, for five days, Abby plays straight and pretends to be Harper's completely platonic roommate. As Abby gets to know Harper's family and childhood friends and struggles to balance her romance with the ruse, she begins to wonder whether the relationship has a future.

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Aside from Stewart and Davis, the Happiest Season cast is full of recognizable actors, comedians, and even drag queens. Aubrey Plaza plays Harper's family friend (and former girlfriend), and Alison Brie portrays her Gwyneth Paltrow-esque older sister. The rest of the ensemble includes a Schitt's Creek favorite, an SNL alum, and a RuPaul's Drag Race winner. Read on for all the familiar faces you'll see in Hulu's first-of-its-kind holiday movie — and where you can watch them next.

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Photo: Courtesy of Hulu.

Kristen Stewart Plays Abby


This is Stewart's first time leading a romantic comedy (unless you consider Twilight a romantic comedy; technically, it could be) but her recent films include Charlie's Angels, Lizzie, and Seberg. If you're looking for something new to stream after Happiest Season, you can find her in the sci-fi horror film Underwater on HBO Max or Amazon Prime.
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Photo: Courtesy of Hulu.

Mackenzie Davis Plays Harper


Davis is best known for her role on AMC drama Halt and Catch Fire and, more recently, in The Turning. Up next, she'll star in the HBO Max adaptation of Station Eleven. If you want more of her, you can head to Netflix and find her opposite Gugu Mbatha-Raw in the award-winning Black Mirror episode "San Junipero."
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Photo: Courtesy of Hulu.

Dan Levy Plays John


Levy is John, Abby's hilarious and emotionally wise best friend. If you haven't already, you can watch him in Schitt's Creek, which he also wrote and produced; if you're on a Christmas kick after Happiest Season, you can also try The Kacey Musgraves Christmas Show, which Levy narrates, on Netflix.
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Photo: Courtesy of Hulu.

Mary Holland Plays Jane


You might recognize Holland, who co-wrote Happiest Season and stars as Harper's oddball sister, from shows like Veep, The Good Place, and New Girl. Recently, she starred in wrestling comedy Golden Arm, and she also voices a character on Netflix's animated sports comedy Hoops.
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Photo: Courtesy of Hulu.

Alison Brie Plays Sloane


Brie plays Sloane, Harper's older, more uptight sister. She's known for her roles on shows including Community and GLOW, but if you're looking for another movie, try eerie Netflix drama Horse Girl. Brie will also appear in Promising Young Woman, out this December.
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Photo: Courtesy of Hulu.

Aubrey Plaza Plays Riley


Plaza's character, Riley, is Harper's first ex-girlfriend and a new friend of Abby's. On Hulu, you can watch her in creepy thriller Child's Play or the satirical dramedy Ingrid Goes West. On Netflix, you can find her in Sarah Cooper's comedy special (or, of course, on Parks and Recreation).
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Photo: Courtesy of Hulu.

Mary Steenburgen Plays Tipper


In recent years, Steenburgen has appeared on shows like Grace and Frankie, Orange is the New Black, and The Good Place. She also stars on the musical comedy Zoey's Extraordinary Playlist, which you can watch on Hulu or Peacock. Currently, she's filming the Guillermo del Toro thriller Nightmare Alley.
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Photo: Courtesy of Hulu.

Victor Garber Plays Ted


Rounding out Harper's family is her father Ted, who is also a possibly-conservative mayoral candidate. He's appeared in classics like Legally Blonde, but you might have also seen him on Tales of the City, DC's Legends of Tomorrow, and The Flash. Next, he'll star in the Canadian drama Family Law.
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Photo: Courtesy of Hulu.

Jake McDorman Plays Connor


McDorman, who you might recognize from Aquamarine and Greek, plays Harper's high school ex. Today, he stars in the Disney+ drama Do The Right Stuff, and he's also appeared on tons of shows you can stream, like What We Do in the Shadows (he plays Jeff, a.k.a. "Jesk") and Watchmen. He's also been tapped for the Hulu mini-series Dopesick, based on the acclaimed nonfiction book by Beth Macy.
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Photo: Amy Sussman/Getty Images.

Ana Gasteyer Plays Harry Levin


Gasteyer, a former SNL cast member, actress, comedian, and singer, has been in everything from Mean Girls to Wine Country. She currently plays a recurring role on The Goldbergs, which you can watch on Hulu. Earlier this year, she also starred on the adult animated series Magical Girl Friendship Squad with Quinta Brunson and Anna Akana.
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Photo: Courtesy of Hulu.

Burl Moseley Plays Eric


Moseley plays Eric, Sloane's former lawyer husband and Harper's brother-in-law. He's known for his role on Crazy Ex-Girlfriend (a show on which he performed a song called "Don't Be a Lawyer"), and he recently voiced his first character on the Apple TV+ animated series Doug Unplugs.
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Photo: Courtesy of Hulu.

Sarayu Rao Plays Carolyn


Along with her starring role on I Feel Bad, Rao has appeared on Station 19, Veep, and The Real O'Neals. She also plays Lara Jean's neighbor, Trina, in Netflix's To All The Boys I've Loved Before trilogy. You can catch her next in the series' final installment, Always and Forever, Lara Jean, which is currently in post-production.
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Photo: Astrid Stawiarz/Getty Images.

Michelle Buteau Plays Trudy


It wouldn't be a good rom-com without Michelle Buteau: in just the past few years, she appeared in Always Be My Maybe, Someone Great, and Isn't It Romantic. You can stream all three of those movies on Netflix or Hulu, but if you really want more Buteau, you should check out her comedy special on Netflix.
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Photo: Courtesy of Hulu.

Jinkx Monsoon


Drag Race winner Jinkx Monsoon appears in Happiest Season at a dive bar drag show. Jinkx acted and voice-acted on shows including AJ and the Queen, Steven Universe, and Capitol Hill, and will soon star with BenDeLaCreme in The Jinkx & DeLa Holiday Special, set to air on the duo's website.
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Photo: Courtesy of Hulu.

BenDeLaCreme

BenDeLaCreme is also a RuPaul's Drag Race alum, and — with Jinkx Monsoon — served as a writer, executive producer, and director for the forthcoming feature The Jinkx & DeLa Holiday Special.
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