? What’s the holiday season for if not tucking in on the couch with a cup of hot cocoa in hand, rewatching your favorite feel-good movies? Despite there being a trove of Holiday-themed movies released every year — some definitely better than others, we’re looking at you, Hallmark — there’s a certain magic to the movies we spent watching, never getting tired of.
We’re taking a look back at the movies that encapsulate the holiday season’s essence: fun, familiar, nostalgic, and wholesome. Still unsure what to watch tonight? We’d recommend tuning into one of these classics…
#1- Home Alone (1990): Watching a rebellious kid wreak havoc on two home robbers never gets old. When eight-year-old Kevin McCallister is left home alone on Christmas eve after his parents simply failed to notice his absence (which is naturally what happens when your nuclear family is the size of a football team), he finds himself the only line of defence against two intellectually challenged robbers who want to walk away with some goodies.
Home Alone is a movie that works because it’s entirely ludicrous — premise to ploys. It’s the kind of care-free, anything goes movie you never tire of, and one no two people (that we know of) would disagree on. If you’re looking for laughs, look no further than Home Alone. You can stream the film on Disney+.
#2- The Holiday (2006): Your watch list can’t be complete without The Holiday. With a star-studded cast comprising Cameron Diaz, Jude Law, Kate Winslet, and Jack Black, the movie is true holiday escapism manifested — both for the viewer, and the characters. Winslet and Diaz’s characters are in a rough spot, with their lives pretty much going haywire. In an attempt to catch a break and escape their ex-partners, the pair decides to swap their homes (and in a way, lives) for Christmas, only for their lives to change for the better — and for good.
The Holiday is an incredibly heartwarming film that evokes a certain sense of nostalgia for days gone by that no other film of the era has been able to quite achieve. You might want to keep a tissue pack handy, but we promise they’ll be happy tears. If you’ve been in a rough spot yourself, we’d argue you’d find some much-needed catharsis here. You can stream the film on Netflix.
#3- You’ve Got Mail (1998): While not strictly a holiday movie, it’s a classic nonetheless. You’ve Got Mail is the kind of movie we find ourselves going back to time and again when we yearn for simpler days. Essentially a story of human connection that eschews pretense, the film follows Joe (Tom Hanks), a big-bad corporate book chainstore owner, and Kathleen (Meg Ryan), a struggling independent bookstore owner. Professionally speaking, these two have it out for each other. On a personal level? They’re actually e-lovers communicating in anonymity via email.
It’s a rom-com that truly stood the test of time, and one that remains to be replicated. Do you love books and cozy bookstores? You’ll be in for a treat. You can stream the film on OSN+.
#4- Die Hard (1988): An action-junkie but still craving the holiday glitz and glamor? The venn diagram between action movies and holiday classics would pretty much be non-existent if it weren’t for Die Hard. Christmas isn’t always the most wonderful time of the year — sometimes your entire family can get held to ransom on Christmas Eve, and that was exactly what happens to John McClane’s (Bruce Willis) family in the film.
An action classic through and through, Die Hard has long been a point of contention for many — does its setting in New York during Christmas qualify it as a holiday movie? Many would argue not. We, however, would say absolutely yes — we could use a palate cleanser between the family dramas. You can stream the film on Disney+.
#5- A Charlie Brown Christmas (1965): Listen up folks, when we said classic, we meant it. Short, sweet, and incredibly wholesome for the holiday season, the 30-minute animated family film is the Christmas classic, and one that — decades later — remains timely and relevant. Based on one of the most popular comic strips in history, Peanuts (1950-2000), the short film follows Charlie, who despite being surrounded by holiday cheer, feels depressed. Somewhere along the way, he feels, the true spirit of Christmas was lost, replaced by an amalgamation of theatrics and material desires. Determined to reignite true holiday joy, Charlie decides to take matters into his own hands.
A Charlie Brown Christmas stood the test of time and then some — yet surprisingly, its creators thought it would end up being a disaster. Little did they know, its ‘faults’ were exactly the reason why it’s still available to stream in 2025. Given its unconventional premise, lack of a laugh track (then ubiquitous), and slow pace, producers had their doubts — all extinguished the second it aired. Looking for a quick, cute watch? Give Charlie Brown a minute (or 30) of your time. You can stream the film on Apple TV.
Honorable mentions: