Billy Crystal as Harry Burns and Meg Ryan as Sally Albright in When Harry Met SallyImage via Columbia Pictures
By
Robert Lee III
Published 44 minutes ago
Writing from the Chicagoland area in Illinois, Robert is an avid movie watcher and will take just about any excuse to find time to go to his local movie theaters. Robert graduated from Bradley University with degrees in Journalism and Game Design with a minor in Film Studies. Robert tries his best to keep up with all the latest movie releases, from those released in theaters to those released on streaming. While he doesn't always keep up with the latest TV shows, he makes it a goal to watch nearly every major new release possible. He has been honing his craft and following any and all movie news all his life, leading up to now, where he has a vast knowledge of film and film history. He also logs every movie that he watches on his Letterboxd page, and has hosted a weekly online movie night with his closest friends for over 6 years.
Sign in to your Collider account
Summary
Generate a summary of this story
follow
Follow
followed
Followed
Like
Like
Thread
Log in
Here is a fact-based summary of the story contents:
Try something different:
Show me the facts
Explain it like I’m 5
Give me a lighthearted recap
More than any other holiday out there, Christmas has lent itself as a prominent time period and tonal style for a wide variety of different films. Even moreso, the holiday spirit has proven to have a great effect on romance and emotionally impactful stories of love, leading to it being one of the most frequent angles for romantic comedies over the years. Whether it be highly acclaimed staples of the romantic comedy genre or the wide array of dumb-fun films released by Hallmark during the holiday season, there is no shortage of Christmas rom-coms worth seeking out.
However, the absolute best of Christmas rom-coms prove to be some of the most celebrated and overall rewatchable films of the entire holiday season. No one can resist the feel-good energy and joy of a great romantic comedy, with the merry energy of Christmas only further amplifying these notions to make them endlessly rewatchable year after year. Several of these Christmas rom-coms are still widely celebrated as some of the best and most iconic rom-coms of their respective eras.
10 'Last Christmas' (2019)
Image via Universal Pictures
Adapted from the iconic Christmas song of the same name, Last Christmas transforms this rather unconventional source material into a memorable rom-com experience, complete with unexpected twists and some genuinely effective charm. While much of the conversation surrounding the film centers on its wildly chaotic twist, the actual film, leading up to its twist, does an effective job of keeping the audience invested and in tune with its emotional core until it subverts all expectations.
Said twist has certainly made it among the more divisive Christmas rom-coms, especially when it was first released, yet time has been surprisingly kind to Last Christmas as more and more people find joy and reverence for its distinct charm. Emilia Clarke and Henry Golding simply work well together as an on-screen couple, with some effective chemistry and dynamic performances with multiple layers after knowing all the moving pieces and twists.
9 'The Family Stone' (2005)
Rachel McAdams, Diane Keaton, and Sarah Jessica Parker having a laugh on the kitchen floor in The Family StoneImage Via 20th Century Fox
One of the most prominent shared experiences that many people have during the holidays is that of reconnecting and meeting with family members for times of joy, chaos, and overall comfort. While many different Christmas rom-coms have found success in implementing romance to this family get-together energy (including a few that will appear later on in this list), no film quite embodies this energy like The Family Stone. More than any other family get-together film, The Family Stone fundamentally understands the mixture of comfort and chaos that an extended family provides during the holidays.
The film acts as a twist and reversal of a more expected fish-out-of-water story, seeing lead character Meredith Morton (Sarah Jessica Parker) as an uptight conservative businesswoman visiting her boyfriend's family of easygoing free spirits. Parker's distinct performance and clashing with the style and wildly comforting energy of the Stone family make for not just a great deal of comedy, but an effective sense of camaraderie and understanding from completely different worldviews.
8 'Serendipity' (2001)
Kate Beckinsale and John Cusack in SerendipityImage via Miramax
One of the greatest aspects of romantic comedies as a genre is their ability to conjure unbelievable stories of chance and impossibility that are tailor-made to lift spirits and have audiences believe in the power of love. Combining that with the signature magic of the holiday season, it's no wonder that Serendipity has been so revered and celebrated by audiences over the years. The story of chances, fate, and the destiny of love has struck a chord with audiences for years, still maintaining what is considered one of the all-time best meet-cutes in rom-com history.
The film follows the separate lives and stories of Sara (Kate Beckinsale) and Jonathan (John Cusack), a duo of strangers who find that they have overwhelming chemistry with one another, despite both being in relationships. Their time with each other on one fateful holiday night is short-lived, but it leaves an undeniable impact on both of them. Now, years later, with both of them about to be married to their respective partners, they still cannot stop thinking about each other, ironic as they are constantly just out of reach of one another.
7 'While You Were Sleeping' (1995)
Bill Pullman and Sandra Bullock talking outdoors at night in While You Were Sleeping.Image via Buena Vista Pictures Distribution
Sporting a classically nonsensical rom-com premise that manages to exude great charm and wit despite the irregular nature of its characters, While You Were Sleeping combines Christmas, amnesia, and false identity to make for an unorthodox rom-com classic. The film sees Sandra Bullock as Lucy, a transit worker who is mistaken for the fiancée of a man in a coma she helped pull off the railway tracks. She decides not to correct them, spending the holidays helping them feel better, but things get complicated when she begins to fall for the man's brother, Jack (Bill Pullman).
While its setup and base premise seem too absurd and complicated to take seriously, its core theming and style as a feel-good Christmas romance based on family connections give it a distinct charm that elevates even the zaniest aspects of its story. Bullock and Pullman do a lot of heavy lifting in terms of elevating their characters, with a palpable on-screen chemistry that grows and gets more entertaining and lovable as the film goes on.
6 'Bridget Jones's Diary' (2001)
Bridget from Bridget Jones's Diary sitting on her couchImage via Universal
A classic rom-com of the 21st century that is as much about its central romances as it is about self-betterment and taking the steps towards a more fulfilling life, Bridget Jones's Diary has been a staple of rom-coms since its release. While the film is more directly associated with New Year's specifically, instead of Christmas, dealing with the notions of resolutions, it is still ingrained with the sense of merriment present within all holiday rom-coms.
The dynamic love triangle of Renée Zellweger, Colin Firth, and Hugh Grant makes for one of the most iconic and effective triangles in rom-com history, with each character adding their own sense of charm and importance to the impact of the film. There's a sense of earnestness to the characterization and story of Bridget Jones's Diary that has made it endearing and timeless for so many years, as the chaotic difficulties of trying to make life better make for an effective backdrop for a rom-com.
5 'Happiest Season' (2020)
Kristen Stewart as Abby and Mackenzie Davis as Harper sit together in a scene from Happiest Season.Image via Hulu
Combining the classic in-laws Christmas rom-com setup with the inherent difficulties and pains of having to hide in the closet from one's family, Happiest Season is the feel-good LGBTQ+ Christmas rom-com that the queer community has been wanting for ages. The film sports an effective central chemistry and dynamic between Kristen Stewart and Mackenzie Davis, and a great supporting cast including the likes of Allison Brie, Dan Levy, and Aubrey Plaza. It also manages to be wildly accessible even to those who aren't LGBTQ+ themselves, adhering to the classic conventions of Christmas rom-coms of the past.
It doesn't exactly break new ground when it comes to what Christmas rom-coms are capable of, but it adheres to the traditions and style of the genre so effectively that it's hard not to have a joyous time watching the film. It mixes together a cozy, holiday energy and comedy with some effective messaging on the importance of staying true to oneself in the face of hardships and a misunderstood family. Especially compared to the wide array of other rom-coms of the streaming sera, Happiest Season has been a breakout hit that is consistently rewatched year after year.
4 'Holiday Inn' (1942)
Linda and Jim, played by actors Marjorie Reynolds and Bing Crosby, sit at a piano and sing together in Holiday Inn.Image via Paramount Pictures
While many of the most celebrated and rewatched holiday rom-coms are relatively modern in the grand scale of filmmaking history, Holiday Inn stands out as one of the longest-lasting and impactful rom-coms that brilliantly utilize the holiday season. The Christmas musical classic has been a staple of Christmas films for generations, with its legendary original song, "White Christmas", having become a staple of the holiday whose legacy has even surpassed that of the film itself.
The actual film itself is surprisingly effective in terms of its blending of musical numbers and a compelling central romance, being about as classic as a holiday rom-com can get. It has a substantial legacy and impact on both the romantic comedy genre and holiday filmmaking as a whole, with elements of its craft and brilliance still being felt in modern releases to this very day. No matter how many years have passed since its release, it continues to be a lighthearted watch that will always brighten up a room with its charm and melancholy energy.
3 'Love Actually' (2003)
Andrew Lincoln in Love Actually holding a sign that says Merry ChristmasImage via Universal Pictures
Easily standing out as one of the most iconic and recognizable original holiday movies of the 21st century, Love Actually has such an endearing quality to its execution that has made it a staple of many households during the Christmas season. It almost feels as if it has been tailor-made to be more heartfelt and effective on each subsequent rewatch, with more joy and entertainment to be found with the film each time its exploration of love is witnessed.
As opposed to a singular love story, Love Actually follows a wide variety of different stories and characters as they intersect and evolve in accordance with the Christmas season and the chaos that it provides. However, each of the stories, as different as they may feel from one another, has something important to say about one's relationship with love as a whole, as the time leading up to the holiday season simply brings out the emotional side of many people.
2 'The Holiday' (2006)
Kate Winslet and Jack Black in The Holiday (2006)Image via Sony Pictures Releasing
While Love Actually has largely stood as the more popular and immediately recognizable holiday rom-com throughout the 21st century, The Holiday has slowly but surely amassed a legacy that has managed to rival that of Love Actually. Its classic mixture of cultures and stories as it follows two distinctly different holiday romances unfolding makes for one of the most heartfelt and feel-good experiences that a holiday rom-com can provide.
The essential 2000s rom-com thrives on the back of its all-star cast, with each of the four main stars bringing their absolute all into fueling the story with personality and wit at every opportunity. The sheer likability of the characters, combined with the cozy nature of its story and the hilarious distinction and shifts between its two settings and styles, has made it a frequent rewatch that has only grown more beloved year after year. Nancy Meyers pulls out all the stops to bring to life what could easily be considered the best film of her directorial career.
1 'When Harry Met Sally' (1995)
Billy Crystal as Harry Burns and Meg Ryan as Sally Albright in When Harry Met SallyImage via Columbia Pictures
When Harry Met Sally is one of the most interesting cases when it comes to its legacy as a Christmas-time rom-com, as while it undeniably stands as an unbridled masterpiece of romantic comedy, its connection to various holidays and time periods ranges from person to person. It comes with the territory of its story ,following the evolution and growth of this core friendship into one of unexpected love, yet a select few significant scenes have made the film iconic for the fall and holiday season.
In terms of its holiday significance specifically, the film's perfect ending at the New Year's Eve party and the various Christmas celebrations during its final act leading up to this point make it some of the best holiday content in any rom-com. No singular scene quite maximizes the impact and weight of a holiday's energy with bustling feelings of love and passion like in this film, with Harry pouring his soul out while "It Had to Be You" plays, being one of the best rom-com scenes of all time. Even if the entire film doesn't exude such overwhelming Christmas energy, the final act alone is so perfectly made that it makes the film such a resounding holiday classic.
Like
When Harry Met Sally
R
Comedy
Drama
Romance
Release Date
July 21, 1989
Runtime
95 minutes
Director
Rob Reiner
Writers
Nora Ephron
Cast
See All-
Bruno Kirby
-
Meg Ryan
Expand
Collapse
-
Movie
We want to hear from you! Share your opinions in the thread below and remember to keep it respectful.
Be the first to post Images Attachment(s) Please respect our community guidelines. No links, inappropriate language, or spam.Your comment has not been saved
Send confirmation emailThis thread is open for discussion.
Be the first to post your thoughts.
- Terms
- Privacy
- Feedback
Jun 3, 2025
10 Rom-Com Flops From the 2000s That Are Already Cult Classics
2 days ago
The 10 Best Movie Soundtracks of All Time, Ranked
3 days ago
The 10 Greatest Noir Movies, According to Letterboxd
2 days ago
The 11 Greatest Movies of the Last 40 Years, Ranked
More from our brands
Movies To Watch If You Like 365 Days
The 40 Best Christmas Movies of All Time, Ranked
Every New Romance Anime Announced For 2025 (So Far)
37 Shows on Netflix That Couples Can Binge-Watch Together
10 Best Holiday Romance Films of the 21st Century
30 Best Movies About Cheating & Infidelity
17 Best Christmas Movies to Put On After the Kids Go to Bed
What To Watch
July 20, 2025
The 72 Best Movies on Netflix Right Now
Trending Now
Move Over, ‘Gilmore Girls’; This Netflix Drama Will Get You in the Perfect Fall Mood
These 7 Movies Are Destined To Get Snubbed at the Oscars (And I’m Already Mad About It)
40 Shows To Watch if You Love 'Slow Horses'
