#1 ‘Home Alone’ (1990)
Where to Watch: Disney+
Genre: Comedy/Family
Rating: PG
Length: 1 hour and 43 minutes
IMDB Score: 7.7 out of 10
Synopsis: When bratty 8-year-old Kevin McCallister (Macaulay Culkin) acts out the night before a family trip to Paris, his mother (Catherine O’Hara) makes him sleep in the attic. After the McCallisters mistakenly leave for the airport without Kevin, he awakens to an empty house and assumes that his wish to have no family has come true. But his excitement sours when he realizes that two con men (Joe Pesci and Daniel Stern) plan to rob the McCallister residence and that he alone must protect the family home.
Zack’s Review: As a child, I used to love watching “Home Alone” during the winter months and dreaming about what it would be like to have the whole house to myself like Kevin McCallister. In the movie, Kevin’s family accidentally leaves him behind on their trip to Paris, but burglars Harry and Marv have their sights set on robbing the empty house. To defend his home, Kevin sets up a series of elaborate traps. Not only is “Home Alone” a hilarious film, but it also has a heartwarming storyline as Kevin’s mother goes to great lengths to reunite with her lost son. If you enjoyed the first movie, be sure to check out the sequel, “Home Alone 2: Lost in New York.” The traps in this one are even funnier, and I personally love seeing the movie set in New York and recognizing many of the locations. Both are must-watch family films.
#2 ‘Ferris Bueller’s Day Off’ (1986)
Where to Watch: Paramount+, Prime Video (Rent for $3.99)
Genre: Comedy/Romance
Rating: PG-13
Length: 1 hour and 43 minutes
IMDB Score: 7.8 out of 10
Synopsis: Ferris Bueller (Matthew Broderick) has an uncanny skill at cutting classes and getting away with it. Intending to make one last duck-out before graduation, Ferris calls in sick, “borrows” a Ferrari, and embarks on a one-day journey through the streets of Chicago. On his trail is high school principal Rooney (Jeffrey Jones), determined to catch him in the act.
Zack’s Review: What better way to spend a break from school/work than watching the ultimate break featuring the Sausage King of Chicago, Ferris Bueller? Ferris manages to pull off the greatest day of truancy ever by taking his girlfriend and best friend on a joyride in a Ferrari, catching a baseball game at Wrigley Field, dancing on a parade float to “Twist and Shout” by the Beatles, and much more. I even visited Willis Tower (formerly known as Sears Tower) in Chicago last February and reenacted the iconic shot of Ferris and his friends leaning their heads against the glass, looking down 1,353 feet. Ferris has a talent for improvising and making the most of every situation and challenge that comes his way, and it’s a joy to watch. There are so many iconic lines from this movie that I still quote and joke about today. It’s one of my top 10 favorite movies of all time and a must-see for those who haven’t yet watched it, as well as a great choice for a rewatch.
#3 ‘Frozen’ (2013)
Where to Watch: Disney+
Genre: Musical/Family
Rating: PG
Length: 1 hour and 48 minutes
IMDB Score: 7.4 out of 10
Synopsis: When their kingdom becomes trapped in perpetual winter, fearless Anna (Kristen Bell) joins forces with mountaineer Kristoff (Jonathan Groff) and his reindeer sidekick to find Anna’s sister, Snow Queen Elsa (Idina Menzel), and break her icy spell. Although their epic journey leads them to encounters with mystical trolls, comedic snowman Olaf (Josh Gad), harsh conditions and magic at every turn, Anna and Kristoff bravely push onward in a race to save their kingdom from winter’s cold grip.
Zack’s Review: I saw “Frozen” for the first time during my freshman year of high school. I was the only teenager in a theater full of young children, all there to watch the movie on its opening weekend. For the first (and probably only) time in my life, I feared that I had outgrown Disney. However, within two weeks the entire planet was singing “Let It Go” and I realized that I was just ahead of the curve on this one. Olaf the snowman is hilarious, and every line he speaks is pure comedic gold. The songs are beautiful, and the twist with the villain at the end is heart-wrenching. “Frozen” is one of the best animated films ever made, and recently, Disney+ added a sing-along version for those who love belting out the songs with their families. If you enjoyed “Frozen,” be sure to watch its sequel and the special “Olaf’s Frozen Adventure,” which is also available on Disney+.
#4 ‘National Lampoon’s Vacation’ (1983)
Where to Watch: Netflix
Genre: Comedy/Adventure
Rating: R
Length: 1 hour and 38 minutes
IMDB Score: 7.3 out of 10
Synopsis: Accompanied by their children, Clark Griswold (Chevy Chase) and his wife, Ellen (Beverly D’Angelo), venture westward from the suburbs of Chicago to the Disneyland-like theme park Walley World. Clark has planned the trip down to the last detail, including seeing the world’s largest ball of twine. However, Clark’s pursuit of adventure is matched by his dimwitted bumbling, leading to a vacation his family will not soon forget.
Zack’s Review: Every parent tries to plan the perfect family vacation that is fun, adventurous, relaxing and great for bonding. However, things don’t always go as planned, as the Griswold family discovers in the classic comedy film “National Lampoon’s Vacation.” Chevy Chase shines as the father trying his best to make the vacation a success despite all the mishaps and absurd situations that arise. My family and I love watching this film and laughing at the ridiculousness of it all. Each small mistake leads to bigger and bigger issues, and it’s a classic film that is guaranteed to bring some laughter to any vacation. If you enjoy this movie, there are four more films in the series, including the 2015 installment, titled simply “Vacation.”
#5 ‘The Family Man’ (2000)
Where to Watch: Peacock, Prime Video $3.99
Genre: Romance/Comedy
Rating: PG
Length: 2 hours and 5 minutes
IMDB Score: 6.8 out of 10
Synopsis: Jack’s (Nicolas Cage) lavish, fast-lane investment broker lifestyle changes overnight when he wakes up in bed lying next to Kate (Tea Leoni), his college sweetheart he left in order to pursue his career. To his horrifying discovery, he realizes that his former life no longer exists. As he stumbles through this alternate suburban universe, Jack finds himself at a crossroads where he must choose between his high-power career and the woman he loves.
Zack’s Review: There are some movies that leave a lasting impact and make you think about your life, what’s important to you and what you want to achieve moving forward. “The Family Man” is one of those films. It tells a relatable and heartwarming story about a man who realizes that he doesn’t have anything meaningful despite thinking he has it all. Nicholas Cage gives a phenomenal performance as he transforms from a cold-hearted businessman into a true “family man.” In fact, I even quoted this movie in my speech before my wedding in June 2021. Make sure to have some popcorn and tissues handy while watching this emotional yet enjoyable film.
#6 ‘Groundhog Day’ (1993)
Where to Watch: AMC+, Prime Video (Rent for $3.99)
Genre: Romance/Comedy
Rating: PG
Length: 1 hour and 41 minutes
IMDB Score: 8.1 out of 10
Synopsis: Phil, a cynical TV weatherman (Bill Murray), finds himself reliving the same day over and over again when he goes on location to the small town of Punxsutawney to film a report about their annual Groundhog Day. His predicament drives him to distraction until he sees a way of turning the situation to his advantage.
Zack’s Review: As we all know, the past few years of the coronavirus pandemic have often felt repetitive and mundane. “Groundhog Day” takes that feeling to a whole new level, as Phil is trapped in a time loop, living the same day over and over again. The movie is set on Groundhog Day in the charming town of Punxsutawney, which looks picturesque in the wintertime. It’s a very funny film, but it also has some deep themes and messages woven throughout. At first, Phil sees his situation as a curse, and he even tries to take his own life (although he always wakes up to the same alarm clock). But as time goes on, he uses his unique situation to become a better, kinder person and to build a relationship with the woman of his dreams. I really enjoy this film and recommend snuggling up with a blanket and a hot chocolate to watch it.
#7 ‘When Harry Met Sally…’ (1989)
Where to Watch: Netflix, HBO Max
Genre: Romance/Comedy
Rating: R
Length: 1 hour and 36 minutes
IMDB Score: 7.7 out of 10
Synopsis: In 1977, college graduates Harry Burns (Billy Crystal) and Sally Albright (Meg Ryan) share a contentious car ride from Chicago to New York, during which they argue about whether men and women can ever truly be strictly platonic friends. Over the next 10 years, they occasionally meet and soon do in fact become fast friends. Now, after all this time, they still find themselves before this complex, ongoing problem of remaining just friends.
Zack’s Review: Wintertime in New York is depicted as peaceful and beautiful on the big screen. It’s a place full of wonder and excitement, where you can meet so many new people. But for Harry and Sally, they can’t seem to stop bumping into each other. This is my favorite romantic comedy, with many hilarious jokes and touching moments. Billy Crystal is one of my favorite actors—who doesn’t enjoy his performance in “Monsters, Inc.” as Mike Wazowski?—and he really gives it his all playing Harry in this feature. The ending of the movie has some of the best dialogue ever written in any movie, period.
#8 ‘Miracle’ (2004)
Where to Watch: Disney+
Genre: Sport/Drama
Rating: PG
Length: 2 hours and 15 minutes
IMDB Score: 7.4 out of 10
Synopsis: When college coach Herb Brooks (Kurt Russell) is hired to helm the 1980 U.S. men’s Olympic hockey team, he brings a unique and brash style to the ice. After assembling a team of hotheaded college all-stars, who are humiliated in an early match, Herb unites his squad against a common foe, the heavily favored Soviet team. As the U.S. squad tries to overcome insurmountable odds and win the gold medal, the team becomes a microcosm of American patriotism during the Cold War.
Zack’s Review: Do you believe in miracles? This masterpiece tells the heroic tale of a bunch of hothead college players attempting to pull off one of the great upsets against the powerhouse Russian hockey team. While the ending is certainly memorable, it’s the entire journey that makes this film so special. It shows Coach Herb’s tireless work ethic and team-building methods as he prepares his USA team for the challenge of a lifetime. The acting is superb, and the musical score immerses you in the film. Whether you’re a hockey fan or not, this is a great movie that everyone can enjoy.
#9 ‘Spider-Man:
No Way Home’ (2021)
Where to Watch: Starz, Prime Video (Purchase for $8.99)
Genre: Action/Adventure
Rating: PG-13
Length: 2 hours and 28 minutes
IMDB Score: 8.3 out of 10
Synopsis: With Spider-Man’s identity now revealed, the friendly neighborhood web-slinger is unmasked and no longer able to separate his normal life as Peter Parker (Tom Holland) from the high stakes of being a superhero. When Peter asks for help from Doctor Strange (Benedict Cumberbatch), the stakes become even more dangerous, forcing him to discover what it truly means to be Spider-Man.
Zack’s Review: While not a conventional Winter Break film, I think it fits perfectly into the theme of school and winter. The film follows Peter Parker starting his senior year of high school which takes place in the fall and ends in late December. Peter is struggling to balance living a dual life as a superhero and student, something that many of us as Modern Orthodox Jews can relate to as we try to be involved in the secular world while also being religious Jews. The film features a number of familiar Spider-Man foes, such as the Green Goblin, Doctor Octopus, Sandman, The Lizard and Electro, who have been transported to the wrong universe. Alongside Peter are Tobey Maguire’s and Andrew Garfield’s versions of Spider-Man in this epic crossover film. It’s one of my all-time favorite movies with some hilarious moments, spectacular fights and emotional scenes. Tom Holland gives a standout performance, and if you haven’t seen this film yet, I highly recommend checking it out as soon as possible.
#10 ‘Ice Age’ (2002)
Where to Watch: Disney+
Genre: Family/Adventure
Rating: PG
Length: 1 hour and 21 minutes
IMDB Score: 7.5 out of 10
Synopsis: Back when the earth was being overrun by glaciers, and animals were scurrying to save themselves from the upcoming Ice Age, a sloth named Sid (John Leguizamo), a woolly mammoth named Manny (Ray Romano), and a saber-toothed tiger named Diego (Denis Leary) are forced to become unlikely heroes. The three reluctantly come together when they have to return a human child to its father while braving the deadly elements of the impending Ice Age.
Zack’s Review: When I was growing up, “Ice Age” was a frequent sleepover party film my friends and I used to watch. While the animation may not be the most impressive by today’s standards, it still holds up pretty well. The humor is suitable for people of all ages, and what I love most about this film is watching the dynamic between the trio of animals as they interact with each other. Despite their different backgrounds, they have great chemistry and are united by their common goal of saving a human baby. It’s a well-done film that will definitely get you in the winter spirit. If you enjoy “Ice Age,” there are four more sequel films that you can watch as well.
By Zack Greenberg
