2020 Holiday Streaming Guide: Dolly Parton, Vanessa Hudgens, and... Fran Drescher?!

Laura Bradley
Courtesy Hulu
Courtesy Hulu

Friends, it is time. For weeks now, I have bitten my tongue. I have sat silent in the knowledge that It is not even Thanksgiving yet! and to say anything about this before would have been annoying. But now it is December, and so I feel very within my rights to say... bring on the holiday movies!

TV holiday movies, traditionally the stuff of cable channels like Lifetime and Hallmark, have made the jump to streaming in recent years. Netflix has established a couple of popular, tried-and-true franchises like the Christmas Prince and Princess Switch series, and this year Hulu made one of the genre’s first LGBTQ entries with Happiest Season. And if the reign of the 12-foot daddy skeletons this autumn taught us anything, it’s that these trying times have convinced us all to embrace the most gonzo aspects of our seasonal festivities this year. Why not curl up with some fuzzy socks and watch some absolutely wild content starring that girl who was in that thing you loved in middle school? (Pro tip: Make sure to have a giant tub of ice cream in your lap as you do it.)

‘Happiest Season’ Isn’t the Queer-Positive Christmas Movie You Wanted (But That’s OK!)

Here, for your perusal, are this year’s best—and most interesting—originals.

Dash & Lily

The thing about Dash and Lily is that they’re as adorable as they are reprehensible—as charming as they are inconsiderate. In other words: Teens! On the surface, this story about a girl whose brothers con her into a Serendipity-like notebook gambit is the holiday rom-com to end all rom-coms. (The series runs for 10 20- to 30-minute episodes.)

Midori Francis plays Lily as a winsome straight arrow, while Austin Abrams’ Dash is a floppy Salinger type. Together, the two build remarkable chemistry, often evoking warmth and intimacy solely through voice-over narration. It’s an enchanting series from beginning to end—sweet and innocent as a mug of cocoa, but with a little comedic kick. Now on Netflix.

Happiest Season

Kristen Stewart? Check. Mackenzie Davis? Check. And Aubrey Plaza? Give her the most checks for this movie.

This one is not, strictly speaking, a made-for-TV movie. The Sony film would have had a theatrical release, were it not for the pandemic, but instead it debuted on Hulu—a boon to all of us who have been cooped up waiting for some delightful, queer Christmas confection.

That said, Happiest Season also might not be as, well, happy, as some of us—[cough], me—would have liked. The film finds Stewart’s character, Abby, forcibly stuffed back into the closet while on a trip to visit her girlfriend Harper’s (Davis) family. But during the trip home, we do still get plenty of the usual hijinks—including someone falling off a roof, some awkward meetings with exes, and a heaping helping of family dysfunction. And even I have to be honest: The chemistry between Stewart and Plaza (yep, Plaza) is worth the whole movie. Now on Hulu.

The Princess Switch: Switched Again

Remember how in The Princess Switch Vanessa Hudgens played a princess and also a lady named Stacey DeNovo from Chicago? (And how Stacey loved to wear a hat that also said “Chicago”?) This year’s sequel, Switched Again, dares to ask: What if Vanessa played a third character? Stacey is now a princess, and Lady Margaret Delacourt (Hudgens with the Parent Trap-like British accent) is pining over the franchise’s certified heartthrob Kevin (Nick Sagar) after their recent break-up. Naturally, our two Hudgenses find a reason to switch places again—but all hell really breaks loose when the third Hudgens, Lady Margaret’s evil cousin Fiona, hatches her own treasonous scheme. In short: It’s glorious. Now on Netflix.

Christmas on the Square

Dolly Parton might’ve already saved our little asses from coronavirus by funding Moderna’s COVID-19 vaccine research—and on top of that she also gave us a movie musical with Christine Baranski playing the lead character, essentially a high-heeled Scrooge. Praise Dolly! As my colleague Kevin Fallon notes, Christmas on the Square is not to be consumed with even an ounce of cynicism; anything of the sort threatens to curdle all its most charming bits. But if you open your heart to this Smokey Mountain goddess and her good words, even the schmaltzy ones, you never know what you might find. Now on Netflix.

The Christmas Setup

This year brings Lifetime’s first holiday romance with an LGBTQ storyline at its center—starring Fran Drescher (!) as the leader of Milwaukee’s local Christmas celebrations. The story: Drescher plays Kate, whose son Hugo (Ben Lewis) comes home with his best friend for the holidays. Kate arranges a meet-cute between her son and his secret crush, Patrick (Blake Lee). The couple’s holiday romance begins to heat up—until Hugo receives a promotion that could send him to, gasp, London! Premieres on Lifetime Dec. 12.

Jingle Jangle: A Christmas Journey

This one’s worth it for the production design alone. Gloriously overstuffed and irrepressibly jolly, David E. Talbert’s Christmas movie—which stars Forest Whittaker, Phylicia Rashad, and Keegan-Michael Key, among others—is a delirious yarn that makes all the more sense once you realize it was originally conceived as a stage musical. And if you’re wondering why it’s giving off some Greatest Showman energy, that might just be the work of choreographer Ashley Wallen—who worked on both films. Now on Netflix.


I’m not going to lie: There’s something about this one that feels like staring into a black hole. Emma Roberts plays a grouchy single named Sloane, who forms a friends-with-benefits-esque arrangement with her “holidate”—a sweatered hunk named Jackson (Aussie Luke Bracey) who becomes her go-to beau for seasonal functions. Because no one wants to be single on Arbor Day! Kristen Chenoweth plays Sloane’s aunt and holidating muse, and Jessica Capshaw (Arizona Robbins from Grey’s Anatomy) plays her sister, Abby. I cannot for the life of me figure out why the title of this film is not “The Holidate,” but either way it has extremely dark energy and should be approached with caution. Now on Netflix.

The Christmas Chronicles 2

The original Christmas Chronicles was a stand-out for Netflix when it premiered in 2018—and although Chris Columbus certainly has the credentials to pull off a festive family flick, it was fair to wonder if he could recapture the canniness of the original. Thankfully, it looks like the Harry Potter and Home Alone 2 director mostly pulled it off and Goldie Hawn is as delightful as ever as Mrs. Claus. Now on Netflix.

Merry Liddle Christmas Wedding

A sequel to last year’s Merry Liddle Christmas, Merry Liddle Christmas Wedding once again follows Kelly Rowland’s Jacquie Liddle and her neighbor-turned-lover Tyler (Thomas Cadrot) as they try to prepare their perfect destination wedding. (On Christmas, of course!) But Jacquie’s family begins crashing the planning of the nuptials My Big Fat Greek Wedding-style, sending Jacquie’s wedding planner packing in a huff. If nothing else, the ceremony promises to be memorable! Now available on Lifetime.

Christmas Waltz

I would be remiss to publish this guide without a nod to Christmas romance queen and Mean Girls alum Lacey Chabert—who has two films coming out this year. The first: Christmas Waltz, which premieres on Hallmark Dec. 3, finds Chabert playing Avery, who faces her fears after a failed wedding with the help of a dance instructor. (As one does!) And then there’s the busily titled Time for Us to Come Home for Christmas, which premieres on Dec. 5: “Five guests are mysteriously invited to an inn to celebrate Christmas,” a plot summary reads. “With the help of the owner Ben, Sarah discovers that an event from the past may connect them and change their lives forever. Premiering on the Hallmark Channel Dec. 3 and Dec. 5, respectively.

One Royal Holiday

All I know about this one is that Aaron Tveit plays a prince in this one—a member of the Royal Family of Galwick, apparently!—and that’s honestly more than enough for me to go on. Premieres on Hallmark Channel Dec. 7.

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