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Movies like 2020 Winterfest Preview Special (2019)

The best movies like 2020 Winterfest Preview Special (2019) are Ricky Gervais: Mortality (2025), Taylor Tomlinson: Have It All (2024) and Winter Castle (2019). If 2020 Winterfest Preview Special hooked you with its tv movie, these 30 similar films are what to watch next, and every pick says why it matches.

Quick picks

  1. Ricky Gervais: Mortality (2025)

    Ricky Gervais tackles life, death and the state of the world in a brutally honest special that spares no topic, even his own mortality.

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this
  2. Taylor Tomlinson: Have It All (2024)

    Can Taylor Tomlinson have it all? From dating woes to dream jobs to inventive dirty talk, she shares life's ups and downs in this stand-up comedy special.

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this
  3. Winter Castle (2019)

    When Jenny attends her sister’s winter wedding at an ice hotel, her heart melts over the best man, the problem is he unexpectedly brings a “plus one,” seemingly dashing her hopes for a wintery romance.

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this
  4. A Royal Runaway Romance (2022)

    Princess Amelia of Bundbury travels across America to explore a budding romance with an artist, only to fall in love with her bodyguard, Grady.

    Why it matches: Recommended by TMDB viewers

    Worth the HypeMovies like this
  5. Three Wise Men and a Baby (2022)

    Three brothers get the surprise of their lives when they are forced to work together to care for a baby over the holidays. As they slowly get the hang of things, they find themselves on unexpected journeys of self-discovery and begin to rebuild their relationships as brothers, as well as the damaged romantic and professional relationships in their respective lives…all while rediscovering their love of Christmas.

    Why it matches: Recommended by TMDB viewers

    Worth the HypeMovies like this
  6. The Late Shift (1996)

    David Letterman vies with Jay Leno and his manager to succeed Johnny Carson, retiring from "The Tonight Show."

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this
  7. Christmas at the Drive-In (2022)

    Sadie Walker is starting over in her hometown of Chesterfield, New York, following a series of major life disruptions that include leaving her law practice after losing her biggest case and no longer being engaged.

    Why it matches: Recommended by TMDB viewers

  8. Kevin Hart: What Now? (2016)

    Comedian Kevin Hart performs in front of a crowd of 50,000 people at Philadelphia's outdoor venue, Lincoln Financial Field.

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this
  9. Jim Gaffigan: Quality Time (2019)

    Comedian Jim Gaffigan performs live at the State Theatre in Minneapolis, MN.

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this
  10. Bill Burr: Drop Dead Years (2025)

    In what might be his most personal and introspective hour yet, Bill offers hilarious takes on everything from male sadness to dating advice.

    Why it matches: Recommended by TMDB viewers

    Worth the HypeMovies like this
  11. John Mulaney: Kid Gorgeous at Radio City (2018)

    John Mulaney relays stories from his childhood and "SNL," eviscerates the value of college and laments getting older in this electric comedy special.

    Why it matches: Recommended by TMDB viewers

    Absolute CinemaMovies like this
  12. A Merry Christmas Wish (2022)

    Janie, a rising marketing executive living in The Big Apple, returns to her hometown of Woodland Falls when her Great-Uncle Randall passes away. Randall has even arranged for his farmhand, Dylan to help at the event, which is being held in the farm’s sprawling barn. Aware that her Manhattan boyfriend is anxious for her to return to the city so the pair can jet off to a previously planned holiday on the beach, Janie begins to feel an unexpected emotional tug about living life in a more authentic, meaningful way.

    Why it matches: Recommended by TMDB viewers

  13. Dave Chappelle: The Closer (2021)

    As he closes out his slate of comedy specials, Dave takes the stage to try and set the record straight — and get a few things off his chest.

    Why it matches: Recommended by TMDB viewers

    Worth the HypeMovies like this
  14. Love in Winterland (2020)

    Ally, a final contestant on a dating show, must face her high school sweetheart when she is chosen for the Hometown Date.

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this
  15. All of My Heart: Inn Love (2017)

    Brian and Jenny are preparing for the grand opening of their bed and breakfast, Emily's Country Inn, when a big storm hits Buck County. Brian agrees to go back to Wall Street to boost their funds, while Jenny scrambles to keep the opening on track.

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this
  16. Jim Gaffigan: Mr. Universe (2012)

    Funnyman Jim Gaffigan offers up his unique take on everything from Disney World to overweight whales in this live show from Washington, D.C.

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this
  17. Love Struck Café (2017)

    Megan Quinn, an aspiring architect, faces multiple tasks – developing her hometown lake into a commercialized entertainment center, forcing Mrs. Frances Figgins, her childhood mentor, out of her family’s home, and helping out at her family café after her father breaks his leg, all while also dealing with the return of her childhood sweetheart, Joe, who broke her heart.

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this
  18. The 27-Hour Day (2021)

    An entrepreneur takes a necessary break from developing her wellness brand empire and discovers that the work-life balance she needs won’t be easy. Will a new romance and relaxing retreat change her life forever?

    Why it matches: Recommended by TMDB viewers

    Worth the HypeMovies like this
  19. Five Star Christmas (2020)

    After moving back to her hometown, Lisa (Lenz) plots with her siblings and grandparents to help her father's bed and breakfast get a five-star review from an incognito travel critic (Webster), but ends up falling for him, not knowing he is the real critic.

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this
  20. Louis C.K.: Hilarious (2010)

    In this unique and dynamic live concert experience, Louis C.K.'s exploration of life after 40 destroys politically correct images of modern life with thoughts we have all had...but would rarely admit to.

    Why it matches: Recommended by TMDB viewers

    Worth the HypeMovies like this
  21. The Maya Rudolph Show (2014)

    Maya Rudolph's take on the variety show special with guest stars in the vein of the Carol Burnett Show.

    Why it matches: Similar story and style

  22. Max Headroom: 20 Minutes into the Future (1985)

    While trying to expose corruption and greed, television reporter Edison Carter discovers that his employer, Network 23, has created a new form of subliminal advertising (termed "blip-verts") that can be fatal to certain viewers.

    Why it matches: Similar story and style

    Popcorn FlickMovies like this
  23. Where's the Love? (2014)

    Married couple Ryan and Sebastian are professional love and relationship therapists, and the stars of the hit television series 'Where Is The Love.' Unfortunately, their love didn't last and they have separated. However, in fear of losing their clients and damaging their reputations, they decide to keep their split a secret and operate as though they are a happily married couple.

    Why it matches: Similar story and style

  24. From Prison: Young Devil Worshipers (1989)

    Devil worship? Could it be real? Follow up to Devil Worship: Exposing Satan's Underground.

    Why it matches: Similar story and style

  25. 2019 Winterfest Preview Special (2018)

    Cozy up by the fire and get a sneak peek at all 5 world premiere original movies coming to Hallmark Channel this January as we celebrate new beginnings during Winterfest.

    Why it matches: Similar story and style

  26. Portrait of a White Marriage (1988)

    Now a famous talk show host, Martin Mull takes his crew and cameras to Hawkins Falls, Ohio with the intent to give his erratic career a fresh start by shooting a special. While the residents are only concerned with taking advantage of his celebrity status, Mull falls for former subject and number one fan Joyce Harrison, who's still very much devoted to her husband Hal.

    Why it matches: Similar story and style

  27. There are so many things you cannot understand (1970)

    Tove Jansson, Erna Tauro, Birgitta Ulfsson, Lasse Pöysti, Gunvor Sandqvist and Bo Andersson have gathered in Tove Jansson's studio to discuss and enjoy the evening. The evening will be accompanied by songs written by Tove Jansson and composed by Erna Tauro.

    Why it matches: Similar story and style

  28. The Star Wars Holiday Special (1978)

    Luke Skywalker and Han Solo battle evil Imperial forces to help Chewbacca reach his imperiled family on the Wookiee planet - in time for Life Day, their most important day of the year!

    Why it matches: Similar story and style

  29. The Reality of Love (2004)

    Ryan Banks's manager and old friend, Todd, comes up with the idea to have Ryan be the bachelor on a reality dating show in order to clean up his image. The only problem is, Todd falls in love with Charlie, the girl Ryan has chosen to propose to.

    Why it matches: Similar story and style

  30. Late Night Nightmare (2023)

    We've reached the final episode of The Late Late Show and James is restless...probably because fellow late night hosts Seth Meyers, Jimmy Kimmel, Stephen Colbert, Jimmy Fallon and David Letterman have some thoughts about his departure.

    Why it matches: Similar story and style

Like 2020 Winterfest Preview Special and something else?

Blend two favourites and we’ll find the films in between.

Frequently asked questions

What are the best movies like 2020 Winterfest Preview Special?

The closest matches to 2020 Winterfest Preview Special are Ricky Gervais: Mortality (2025), Taylor Tomlinson: Have It All (2024) and Winter Castle (2019). Below are 27 more, each with the reason it matches.

What should I watch after 2020 Winterfest Preview Special?

Start with Ricky Gervais: Mortality (2025), the closest match to 2020 Winterfest Preview Special.

What is the highest-rated movie like 2020 Winterfest Preview Special?

John Mulaney: Kid Gorgeous at Radio City (2018), rated 7.9/10 by 259 TMDB users.

What is the newest movie like 2020 Winterfest Preview Special?

Ricky Gervais: Mortality (2025) is the most recent release on this list.

Are there English movies like 2020 Winterfest Preview Special?

Yes: Ricky Gervais: Mortality (2025), Taylor Tomlinson: Have It All (2024) and Winter Castle (2019).

How are movies similar to 2020 Winterfest Preview Special chosen?

First come films that Trakt’s viewers watch alongside 2020 Winterfest Preview Special, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.

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