As a millennial big sister, I am currently take on the delightful task of educating my Gen Z little sister on all the movies that shape our youth.
Sitting down with my best friend in the form of my eager young sibling, we embark on a cinematic journey through a magical world of great movies, according to me.
My sister is twenty-two years young and finishing her final year of college. We have a large age gap, 12 years to be exact. Our childhood/teenage movie experiences are vastly different. And so, the Big Sis Movie Watchlist aka the Gen Z Must Watch Movie List is created.
The list ranges from iconic romantic comedies that make you laugh and cry to Academy Award-winning films that leave an indelible mark. These are more than just movies—they are cultural touchstones.
When we are talking about the heartfelt coming-of-age movies that every young woman should experience, love stories that define the millennial generation, and the timeless tales that continue to resonate with young people today, it is more than just a nostalgic trip down memory lane.
We are blending our generational experiences and creating a shared appreciation for the Millennial Must-Watch Movies.
Why This List…
This innocent conversation quickly turns into a 50+ movie list for her to watch throughout the summer, and I figure I will share this big sister advice with other Gen Z’s (or even the older Gen Alpha’s).
These are the movies that shape us, featuring quotable moments you may hear and not understand—until now.
My favorite re-watch so far is “10 Things I Hate About You.” It is a great way to introduce her to the magic of ’90s teen rom-coms before sending her on her way to finish the list on her own.
We also explore blockbuster movies—those great movies that dominate theaters and become cultural phenomena.
(Blockbuster is a place, an actual store, that we go and rent VHS movies from.)
In this epic movie marathon list, you will delve into iconic films featuring unforgettable performances by stars like Jake Gyllenhaal, Anne Hathaway, and the late Heath Ledger.
These great films are now easily accessible on platforms like Amazon Prime, which allow you and your little sister (or brother) to bond over a shared love for cinema.
This is your warning…
Get ready for belly laughs at great movies showcasing antics of BFFs Romy and Michele, swoon over first kisses with heartthrobs like Chad Michael Murray, and get lost in the magical adventure of childhood favorites.
Each movie is a nostalgic reminder of why these stories captivate us, and seeing my sibling’s eyes light up with the same joy I felt years ago is truly heartwarming. Together, we can bridge a generational gap and prove that the magic of these films is timeless.
Some favorite moments we share are just talking with my younger sister about the fierce and fabulous Elle Woods, whose journey in “Legally Blonde” exemplifies perseverance and self-belief. Compiling this list of the best movies becomes a cherished project, blending the perspectives of an older sister and a younger sister.
We cover everything from blockbuster movies that define our era to heartfelt tales of single mothers making it in the big city.
As we make our list, my sister asks me the question, “What’s that movie where the girl dies?… I think she was sick or something.” GASP
She is referring to “A Walk to Remember.” After correcting her lack of knowledge of this timeless love story that resonates with teenage girls across generations.
So, grab your snacks, grab your cozy blankets, and buckle up for the ride through these timeless classics and contemporary titles. And for those born between 1981 and 1996, also known as Millennials, get ready for a nostalgic trip down memory lane!
1. E.T. The Extra-Terrestrial (1982)
A young boy befriends a gentle alien stranded on Earth and helps him find a way home. This heartwarming tale of friendship and adventure is a Spielberg classic.
Samantha’s 16th birthday is forgotten by her family, leading to a series of comedic and heartfelt events. A quintessential John Hughes film that captures teenage angst.
Five high school students from different cliques spend a Saturday detention together and discover they have more in common than they thought. A defining movie about teenage life and identity.
A group of kids finds an old treasure map and sets off on an adventure to find a legendary pirate’s treasure. It’s a perfect mix of adventure, comedy, and coming-of-age moments.
John McClane, an NYPD officer, battles terrorists in a Los Angeles skyscraper to save his wife. This action-packed thriller redefined the action genre.
A young girl, on the threshold of her teen years, finds her life turning upside down when an unlikely friend accompanies her.
George Banks and his wife, Nina, are the proud parents of Annie, but when she returns from studying abroad and announces that she’s engaged, their whole world turns upside down, especially that of overprotective George. From meeting the in-laws to wedding plans with an over-the-top consultant and his flamboyant assistant, it seems as if the troubles never end in this update of the classic Spencer.
8. Fried Green Tomatoes (1992)
Evelyn Couch is having trouble in her marriage, and no one seems to take her seriously. While in a nursing home visiting relatives, she meets Ninny Threadgoode, an outgoing old woman, who tells her the story of Idgie Threadgoode, a young woman in 1920’s Alabama. Through Idgie’s inspiring life, Evelyn learns to be more assertive and builds a lasting friendship of her own with Ninny. A Balta Film Award 2x nominee.
9. A League of Their Own (1992)
During WWII, a women’s baseball league is formed, and two sisters join the team, experiencing the highs and lows of professional sports. A true story celebrating women’s contributions to sports. A 2x Golden Globes nominee.
Tom Hanks gives an astonishing performance as Forrest, an everyman whose simple innocence comes to embody a generation in this 6x Oscar winning performance.
Cher’s world unravels with the sudden appearance of two hunks: a sexy new classmate, and her square but cute ex-stepbrother. Now she’s learning that when it comes to love, she’s Clueless.
The epic tale of Scottish warrior William Wallace who leads his countrymen in a rebellion against English rule. Mel Gibson’s portrayal of Wallace is both inspiring and heroic. Mel Gibson directed and stars in this rousing 1995 Best Picture Oscar(R)-winner about 13th-century Scottish patriot William Wallace.
Four teenagers discover an old video game console and are literally drawn into the game’s jungle setting – becoming the adult avatars they chose. Robin Williams stars in this thrilling adventure filled with excitement and special effects.
Leonardo DiCaprio and Oscar nominee Kate Winslet light up the screen as Jack and Rose, the young lovers who find one another on the maiden voyage of the “unsinkable” R.M.S. Titanic.
15. Romy and Michele’s High School Reunion (1997)
Two quirky best friends invent fake careers to impress their former classmates at their high school reunion. A hilarious and heartwarming tale of friendship and self-acceptance.
Two secret agents, played by Will Smith and Tommy Lee Jones, protect Earth from extraterrestrial threats while keeping their existence hidden from the public. This sci-fi comedy is known for its witty humor, imaginative alien designs, and action-packed sequences.
In this Cinderella story, a 16th-century woman who is treated as a servant by her stepmother, ends up winning the heart of the French prince.
When a young woman becomes romantically involved with an older divorced man, she must learn how to become the stepmother to his children from his ex-wife – who is terminally ill with cancer. This tear-jerker explores complex family dynamics.
Birdee Pruitt (Sandra Bullock) has been humiliated on live television by her best friend, Connie (Rosanna Arquette), who’s been sleeping with Birdee’s husband, Bill (Michael Paré). Birdee tries starting over with her daughter, Bernice (Mae Whitman), by returning to her small Texas hometown, but she’s faced with petty old acquaintances who are thrilled to see Birdee unhappy — except for her friend
20. Saving Private Ryan (1998)
Based on a World War II drama. US soldiers try to save their comrade, paratrooper Private Ryan, who’s stationed behind enemy lines. Steven Spielberg’s film is renowned for its realistic portrayal of war.
Identical twins separated at birth meet at summer camp and plot to reunite their divorced parents. Lindsay Lohan’s dual role is charming in this fun family film.
22. 10 Things I Hate About You (1999)
Kat Stratford (Julia Stiles) is beautiful, smart and quite abrasive to most of her fellow teens, meaning that she doesn’t attract many boys. Unfortunately for her younger sister, Bianca, house rules say that she can’t date until Kat has a boyfriend, so strings are pulled to set the dour damsel up for a romance. Soon Kat crosses paths with handsome new arrival Patrick Verona (Heath Ledger). A modern retelling of Shakespeare’s “The Taming of the Shrew,” set in a high school. This teen romantic comedy features sharp wit and memorable performances.
A journalist enrolls in her old high school as part of her research for a story and gets a second chance at teenage life and love. Drew Barrymore’s endearing performance makes this a delightful watch.
This hit teen RomCom stars Freddie Prinze, Jr. as a jock who bets he can turn any girl into the ultimate Prom Queen. For school nerd Laney Boggs (Rachael Leigh Cook), fate intervenes and turns an initially deceitful attraction into a genuine romance. A high school jock makes a bet that he can turn a nerdy girl into the prom queen. This film is a quintessential ’90s teen makeover story.
The original gross-out comedy classic! Join Stifler, Jim and the rest of the gang as they attempt to lose their virginity before graduating from high school.
Spunky members of a suburban high school cheerleading squad discover their routine was stolen from a rival school – now they’ve got to devise a completely new set of moves before the national championship!
A once great Roman commander is captured by the malevolent heir to the Emperor’s throne. Forced into exile, he trains as a gladiator in the hopes to one day enact his revenge. Russell Crowe stars in this epic historical drama.
28. Remember the Titans (2000)
Based on the true story of a high school football team that overcomes racial tensions to achieve success. Denzel Washington delivers an inspiring performance as the team’s coach.
Graced with a velvet voice, 21-year-old Violet Sanford heads to New York to pursue her dream of becoming a songwriter only to find her aspirations sidelined by the accolades and notoriety she receives at her “day” job as a barmaid at Coyote Ugly. This film blends music, romance, and the pursuit of dreams.
30. The Wedding Planner (2001)
A workaholic wedding planner’s dedication to her job has kept her from finding the man of her dreams. Then she meets Mr. Right – and he’s the groom in the biggest wedding of her career! Jennifer Lopez and Matthew McConaughey star in this charming romantic comedy.
Dumped for being dim, a colorful co-ed vows to win back her boyfriend by getting herself into Harvard Law School. Reese Witherspoon shines in this empowering and hilarious film.
32. The Princess Diaries (2001)
A socially awkward but very bright 15-year-old girl being raised by a single mom discovers that she is the princess of a small European country because of the recent death of her long-absent father, who, unknown to her, was the prince of Genovia. Anne Hathaway’s breakout role is both funny and heartwarming.
A peasant squire poses as a knight and competes in tournaments to achieve glory and win the heart of a noble lady. This Heath Ledger film blends medieval adventure with a modern rock soundtrack.
34. Save the Last Dance (2001)
Sara is a small-town girl who dreams to become a world-class ballerina. But when her mother suddenly dies, she must abandon her plans and join her estranged father on Chicago’s South Side. This film explores themes of race, romance, and ambition.
The story of two North Carolina teens, Landon Carter and Jamie Sullivan, who are thrown together after Landon gets into trouble and is made to do community service. Mandy Moore and Shane West star in this tear-jerking romance.
A small town girl has made a name in NYC as a fashion designer. She’s set to wed the mayor’s son except for one little detail – getting the husband she left behind to sign the divorce papers! With Patrick Dempsey and Reese Witherspoon.
Teenager Cady Heron must assimilate into Girl World to survive high school life after joining “The Plastics.” After she makes the mistake of falling for the Queen Bee Regina George’s ex-boyfriend Aaron, Cady must reckon with the true nature of high school. This cult classic is both hilarious and insightful about teen life.
A thousand years before the time of Christ, Trojan prince Paris abducts the legendary Greek beauty Helen, queen of Sparta, starting a war led by heroes Achilles and Hector that devastates the ancient world. Brad Pitt stars in this grand historical drama.
Behind every great love is a great story. Two teenagers from opposite sides of the tracks fall in love during one summer together, but are tragically forced apart. Ryan Gosling and Rachel McAdams deliver unforgettable performances in this romantic drama.
A listless and alienated teenager decides to help his new friend win the class presidency in their small western high school, while he must deal with his bizarre family life back home. This offbeat comedy has become a cult classic for its unique humor.
A commitment-averse man finds the love of his life – but her short-term memory condition means she forgets about him every morning! Can the man keep the girl falling in love with him every day? Adam Sandler and Drew Barrymore star
Meet high school student Sam who scrubs floors at a diner, copes with her wicked stepmother and stepsisters, and all the while dreams of Princeton. It’s a modern-day retelling of the classic fairy tale, where a high school girl, played by Hilary Duff, overcomes her wicked stepmother and stepsisters to find love. This charming romance emphasizes the importance of being true to oneself.
As a baby, Ella receives a visit from Lucinda and is bestowed with a magical talent that requires her to obey anything she is told to do. This is more of a curse than a blessing once her mother dies and she is forced to live with Dame Olga. Anne Hathaway stars in this enchanting and humorous fantasy adventure.
44. The Sisterhood of the Traveling Pants (2005)
Four best friends discover a pair of jeans that fits each of them perfectly and share it over a summer of separate adventures. This heartfelt film explores themes of friendship, love, and personal growth. A coming of Age Adventure based on Ann Brashares’ best-selling novel about a special 16th summer in the lives of four lifelong friends who are separated for the first time.
45. John Tucker Must Die (2006)
Three ex-girlfriends of a serial cheater set up their former lover to fall for the new girl in town so they can watch him get his heart broken. This comedic film highlights the power of female friendship and teamwork.
46. The Devil Wears Prada (2006)
Meryl Streep and Anne Hathaway star in this film about a college graduate who goes to work for the boss from hell at a fashion magazine. A young aspiring journalist lands a job as an assistant to a powerful fashion magazine editor, played by Meryl Streep.
A lonely doctor who once occupied an unusual lakeside home begins exchanging love letters with its newest resident, a frustrated architect. Keanu Reeves and Sandra Bullock star in this romantic drama with a unique time-travel twist.
Determined to have sex before leaving for college, two teenagers agree to buy the booze for the coolest party in town, leading to a night they’ll never forget. This raunchy comedy is a coming-of-age story about friendship and growing up.
A meddling mother tries to set her daughter up with the right man so her kid won’t follow in her footsteps. Diane Keaton and Mandy Moore star in this comedic and heartfelt exploration of family dynamics.
After a blow-out bachelor party, three groomsmen wake in their Las Vegas hotel room to find the groom is missing and they can’t remember a thing about what they did the night before. This outrageous comedy is packed with wild escapades and unexpected twists.
When a clerical error causes a clash in wedding dates, two best friends who’d do anything for each other find themselves in a no-holds-barred, take-no-prisoners struggle that threatens to erupt into all-out war. Kate Hudson and Anne Hathaway star in this hilarious film about friendship and competition.
She’s a Type-A Manhattan executive with a she-devil reputation, he’s her harried assistant – but getting this odd couple married is the only way she won’t lose her immigration visa in this deft comedy. With Betty White, Sandra Bullock and Ryan Reynolds. Bullock and Reynolds’ chemistry makes this romantic comedy a delight.
53. Love and Other Drugs (2010)
A womanizing pfizer drug rep with no sense of direction or responsibility falls in love with a young woman afflicted with parkinson’s… Jake Gyllenhaal and Anne Hathaway deliver powerful performances in this romantic drama.
After a little white lie about losing her virginity gets out, a clean cut high school girl (Emma Stone) sees her reputation tarnished until she decides to use the rumor mill to advance her social and financial standing. This witty and modern retelling of “The Scarlet Letter” highlights the complexities of reputation and integrity in the digital age.
From the producer of Knocked Up, Bridesmaids Unrated takes Maid of Dishonor, Annie (Kristen Wiig), and four wild bridesmaids on an outrageous ride to their friend’s wedding. This comedy, starring Kristen Wiig, is celebrated for its hilarious and heartfelt portrayal of female friendship.
Free Movie Watchlist Download…
Download this free Big Sis Movie Watchlist. Use this to fill in which movies you want to watch and rank them accordingly. I am a generous 5 star rater thanks to the nostalgia involved with re-watching all the movies on the list.
Comment below any that I missed and which ones are your favorites!
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