If you’re anything like me and constantly ask yourself, what movie should I watch tonight, our list of classic movies is your go-to guide. From the 60s to the 2000s, this guide covers the best romantic comedies and chick flicks that every girl needs to watch at least once in her lifetime.
Anytime I’m bored or have nothing to do, I ask myself what movie should I watch. And since I’m a lover of chick flicks and rom-com movies, I think there needs to be a definitive list of girly movies every woman (of course, men can watch, too) has to have seen in her lifetime. In fact, most classics are rewatchable, a lot of them are our favorites and we’ve watched them more times than we can count. After all, there have to be movies you can just watch without having to use your brain’s processing power!
So let’s take a look at our guide and you’ll never have to wonder what movie should I watch tonight.
What Movie Should I Watch?
You need not ask yourself what movie should I watch ever again, just keep this list of best romantic movies/ fun girly flicks with you at all times!
Mean Girls (2004)
Lindsay Lohan, Amanda Seyfried, Rachel McAdams
Cady, the new girl in school falls for the school queen bee’s ex-boyfriend. So of course, drama ensues and Cady has a hard time figuring out who her real friends are. If anyone asked me, what movie should I watch on a girl’s sleepover night, this is the one I’d recommend. Such a classic, and still relevant! Plus, mean girl Regina George is terrible and awesome all at the same time!
Breakfast at Tiffany’s (1961)
Audrey Hepburn, George Peppard
This movie was a great moment not just for the film industry but for the fashion world as well. Every fashion lover has to watch this film about the complicated relationship of a New York socialite and a writer at least once. This classic has great fashion, and of course, some very memorable moments. Plus, it’s one of the best of Audrey Hepburn, and also has a song by her called “Moon River”.
The Holiday (2006)
Cast: Kate Winslet, Cameron Diaz, Jude Law
Two women from different countries decide to switch homes for a while to get away from their relationship troubles. But they end up falling for two local men. It’s one of the best girly classic movies out there.
John Travolta, Olivia Newton-John
Lovers of musical films should definitely watch this one! An Australian vacation fling leads to something much more for Danny and Sandy.
She’s the Man (2006)
Amanda Bynes, Laura Ramsey, Channing Tatum
A high school girl disguises herself as a boy to play football in a tournament after the girls team is cancelled. The entire movie is super hilarious, it’s gotta be one of the best comedy movies on Netflix. Also, it stars Channing Tatum. I don’t see any reason to not watch this rom com!
Freaky Friday (2003)
Jamie Lee Curtis, Lindsay Lohan
The bodies of a mom and daughter who don’t get along at all, get switched and they’re both forced to live the other’s life and learn a couple of things as they go.
13 Going on 30 (2004)
Jennifer Garner, Mark Ruffalo
Jenna, a 13 year old girl wakes up one day as a 30 year old woman. Super funny and super entertaining!
Pretty Woman (1990)
Richard Gere, Julia Roberts
This chick flick is another one of the greatest classic movies of all time. A wealthy businessman hires Vivian, to be his escort for social events for a week. But before he knows it, he’s falling for her. This dream come true is a modern fairy tale that you can watch again and again!
How to Lose a Guy in 10 Days (2003)
Kate Hudson, Matthew McConaughey
Benjamin makes a bet that he can make a girl fall for him in just ten days. He meets Andie who’s writing an article on how to lose a guy in ten days. They’re both completely unaware of each other’s secret so it gets really funny and that’s what makes this one of the best 2003 movies. Plus Matthew McConaughey is super hot!
10 Things I Hate About You (1999)
Heath Ledger, Julia Stiles, Joseph Gordon-Levitt
Cameron, a teen is not allowed to date Bianca until her older sister, Kat, a bad-tempered and anti-social girl has a boyfriend. So he pays Patrick Verona, the school’s bad boy and rebel to ask Kat out. This film is easily one of my favorite 1990s movies.
Alicia Silverstone, Paul Rudd
This movie needs no introduction or explanation. Any chick flick lover would have already seen this popular high school movie and obsessed over Cher and Dionne’s fashion. It’s also one of my favorite 90s movies ever. Additionally, their clothes are some of the best 90s Theme Party Outfits to Try for Decade Day or a 90s party.
Legally Blonde (2001)
Reese Witherspoon, Luke Wilson
Elle Woods is a sorority girl, poles apart from her boyfriend who dreams of becoming a lawyer. After Elle’s boyfriend breaks up with her for a smarter girl and heads to Harvard Law School, Elle decides to go after him by joining the same school. Lots of drama and wit ensues!
27 Dresses (2008)
Katherine Heigl, James Marsden
My personal favorite among all the 2008 movies has got to be 27 Dresses. It’s based on Jane, a bridal attendant, who comes to find out that her younger sister is engaged to George who is not only her boss but also the man she’s secretly in love with.
Notting Hill (1999)
Hugh Grant, Julia Roberts
The life a British bookseller changes after he falls for a famous American actress. It’s one of the those classic movies that you can watch over and over again.
Sleepless in Seattle (1993)
1993; Tom Hanks, Meg Ryan
A widowed man’s son calls up a radio talk show in hopes of finding his dad a partner. Quite a slow-paced film but enjoyable, nevertheless! This is the kinda relaxing chick-flick I like to watch when I’m wondering what movie should I watch during a long flight!
Kate & Leopold (2001)
Meg Ryan, Hugh Jackman
A duke from the 1800s finds himself in the modern day world and falls for a young advertising executive. This is a classic fairy tale with a modern twist!
When Harry Met Sally (1989)
Billy Crystal, Meg Ryan
If you asked me what movie should I watch with my boyfriend, I’d definitely say this one. Chance encounters, star-crossed love, destiny and tons of humor – this epic movie has it all!
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The Princess Diaries (2001)
Julie Andrews, Anne Hathaway
This one’s probably one of the first chick flicks I ever watched. And as cliche as it may be, I never get sick of it. It’s about a regular high schooler, Mia, who learns that she is the daughter of the prince of Genovia on her 16th birthday. This makeover movie is a total classic and charmingly relatable!
Dirty Dancing (1987)
Patrick Swayze, Jennifer Grey
Anytime my friends ask me, “What movie should I watch to cheer me up,” I always suggest Dirty Dancing. It’s such a feel good film with lots of music and dancing and of course, the gorgeous Patrick Swayze. While on a family vacation, Baby, a young woman develops feelings for the resort’s dance instructor, who her father does not approve of. You have to watch this movie at least for that iconic lift scene at the end! Plus, the music is to die for – you’ll want a playlist as soon as you’re done watching the movie!
Love Actually (2003)
Hugh Grant, Martine McCutcheon, Liam Neeson
A romantic and interesting story of 8 different couples and how they deal with their individual complicated relationships.
Pride & Prejudice (2005)
Keira Knightley, Matthew Macfadyen
Based on Jane Austen’s novel, this beautiful movie revolves around Mr. Darcy’s pride and Elizabeth’s prejudice. By far, one of the best film releases of 2005.
Mamma Mia! (2008)
Meryl Streep, Pierce Brosnan, Amanda Seyfried
Sophie, a bride-to-be, has no clue who her father and is determined to find him before she walks down the aisle. So she secretly invites three men from her mother’s past to the wedding. A good movie for teens and adults alike!
500 Days of Summer (2009)
Zooey Deschanel, Joseph Gordon-Levitt
Our classic movies list would not be complete without this film. It’s not your run-of-the-mill chick flick about a man who falls in love with a woman who doesn’t believe in true love.
The DUFF (2015)
Mae Whitman, Bella Thorne, Robbie Amell
One of the best films on Netflix, the DUFF is the most relatable and realistic movie out there. A must-watch for teens!
A Cinderella Story (2004)
Hilary Duff, Chad Michael Murray
This film is one of the best high school movies ever. I’m no longer in high school or a teen but I still love watching it. It’s a modern take on the classic Disney film, Cinderella.
Bride Wars (2009)
Kate Hudson, Anne Hathaway
This one’s gotta be one of my favorite Anne Hathaway movies. It’s about two BFF’s who turn into sworn enemies when both their weddings get scheduled for the same date. If you’ve ever wondered what movie should I watch with friends, this is a great idea.
Amy Adams, Susan Sarandon, James Marsden
A great movie with a completely unique concept! It’s a mashup of an animated world and the real world we live in. After being banished from kingdom in the cartoon world, princess Giselle gets transported to the real world and falls for a lawyer, who already has a girlfriend. Another movie of similar title, Ella Enchanted, starring Anne Hathaway, is also worth a watch.
The Devil Wears Prada (2006)
Anne Hathaway, Meryl Streep
A small town girl lands a highly sought after job as the assistant to a fashion magazine editor aka the boss from hell. In my opinion, it’s one of the greatest chick flick movies ever made, and it’s a must-watch for anyone who loves fashion! Plus, Meryl Streep is awesome as Miranda Priestly!
Everything, Everything (2017)
Amandla Stenberg, Nick Robinson
Movies based on books go wrong most of the times. But this isn’t one of them. It’s a fairly new film and I can already tell it’s gonna be a cult classic in the future. It’s hard to explain the plot without giving too much away. But what I will say is it’s one among the best movies from 2017.
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Sweet Home Alabama (2002)
Reese Witherspoon, Patrick Dempsey
Seven years after filing for a divorce, Melanie returns to her hometown, Alabama, from New York to get her husband to sign the papers. On getting there, she realizes her glamorous life in New York has got nothing on her simple one back home.
50 First Dates (2004)
Adam Sandler, Drew Barrymore
This movie depicts a complicated but beautiful love story of a man who falls for a woman with short-term memory loss. It’s also one of the best 2004 movies.
Bridget Jones’s Diary (2001)
Renée Zellweger, Colin Firth
Bridget, a young British woman, decides to finally take control of her life by keeping a diary where she writes down all her attempts of looking for love. I also recommend the book of the same title.
Miss Congeniality (2000)
Sandra Bullock, Michael Caine
A tomboy detective, Macie is required to go undercover as a beauty pageant contestant. One of the best romantic comedy movies of the 2000s!
Winona Ryder, Christian Slater
High school movies are my favorite! This is probably one of the old films on our list of classic movies but it’s also one of the best. Veronica, a high schooler, teams up with a twisted sociopath, Danny, to kill the cool kids in school.
Jennifer Lopez, Michael Vartan, Jane Fonda
Charlotte meets the man of her dreams but his mother’s determined to do anything to destroy their relationship. How relatable is that!
My Best Friend’s Wedding (1997)
Julia Roberts, Dermot Mulroney, Cameron Diaz
This 90s film is my favorite Julia Roberts movie ever! On learning that her best friend, Michael, is about to marry another woman, Julianne, who’s always had feelings for him, tries to sabotage their wedding.
Maid in Manhattan (2002)
Jennifer Lopez, Ralph Fiennes
A politician falls in love with a maid, thinking she’s a socialite, after seeing her try on an expensive dress.
Confessions of a Shopaholic (2009)
Isla Fisher, Hugh Dancy
If you ever find yourself asking what movie should I watch when you’re bored, this hilarious and light-hearted romantic comedy is always a good option. A girl with a serious shopping addiction is knee deep in debt and tries endlessly to avoid her debt collector. Funnily enough, she lands a job as a financial journalist. Almost all Isla Fisher movies are great but this one, I never get sick of.
Something Borrowed (2011)
Ginnifer Goodwin, Kate Hudson
Rachel is head over heels in love with the man who’s about to marry her best friend. Awkward!
Leonardo DiCaprio, Kate Winslet
A classic yet tragic story based on the sinking of the RMS Titanic ship. Jack and Rose meet on board the ship and fall for each other but of course, all good things come to an end. Titaniv is one of the most popular 90s movies, and also one of the top grossing movies of all time. Plus, Leonardo DiCaprio is super cute!
Romy and Michele’s High School Reunion (1997)
Lisa Kudrow, Mira Sorvino
Two BFF’s cook up huge stories about their career and personal lives in order to impress their classmates at their high school reunion. One of the best 90s movies in my opinion!
Never Been Kissed (1999)
Drew Barrymore, David Arquette
A journalist for the Chicago Sun Times goes undercover to report on the high school scene. A must-watch movie for lovers of cheesy chick flick.
Music and Lyrics (2007)
Hugh Grant, Drew Barrymore
A young woman helps a washed out 80s pop star make a comeback in the music industry.
The Notebook (2004)
Gena Rowlands, James Garner, Rachel McAdams
Another one of the popular movies based on books, The Notebook is a heart-breaking story about two people who can’t be together because of their different backgrounds.
Kevin Bacon, Lori Singer
Musical movies are the best kind of films to watch when bored! Ren and his family move from a big city to a small town, where he discovers that rock music and dancing are considered illegal.
P.S. I Love You (2007)
Hilary Swank, Gerard Butler
A young widow finds out that her late husband has left behind 10 letters for her to help move on from her loss. It’s one of those sad movies that’ll leave you bawling your eyes out from start to end.
The Proposal (2009)
Sandra Bullock, Ryan Reynolds
Margaret, a mean boss, forces her assistant, Andrew to marry her in a desperate attempt to keep her visa and not be deported. Reluctant at first, Andrew asks for a promotion in exchange. But how long will they able to keep up their pretence?
Eat Pray Love (2010)
Julia Roberts, James Franco, Javier Bardem
Not at all satisfied with her life, a young woman travels to three different countries in order to find her true self. One of the most meaningful films I’ve watched, this one’s based on a bestselling chick-lit book of the same name.
The Ugly Truth (2009)
Katherine Heigl, Gerard Butler
When anyone asks me what movie should I watch, most of the times, I recommend Katherine Heigl movies. Just ’cause they appeal to all ages. Mike, a young man who host a TV show segment called the ugly truth, has a cynical and chauvinistic take on love. Abby, a young woman and a firm believer of true love decides to show him he’s wrong.
Before Sunrise (1995)
Ethan Hawke, Julie Delpy, Andrea Eckert
A romantic movie set in the short span of just one night, Before Sunrise is about two 20-somethings, Jesse and Céline who meet on a train and spend an evening together roaming around in Vienna. They developed feelings for each other over conversations about anything and everything and yet, they both know they’ll probably never meet again.
So those were our recommendations for all of you who’ve asked us this question, “What movie should I watch!” Do you have any more films to add on to our list of cult classic movies or girly chick-flicks? Tell us by tweeting @shilpa1ahuja!
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Nishita is a Staff Writer/ Journalist at ShilpaAhuja.com. She is a graduate of National Institute of Fashion Technology and has a degree in leather design. A lover of all things fashion, she writes about everything from beauty, hair and lifestyle to fashion trends and how-to’s. Her area of expertise is outfit ideas but being fresh out of college, she also loves writing about college fashion. Her new found love of baking is currently taking over her life, making her write about all things chocolate and easy recipes. With a flair for sketching and a great eye for detail, she’s previously designed leather garments for brands like Diesel and Salsa. When she’s not writing, she’s busy reading extremely sappy Nicholas Spark’s novels, sewing clothes and listening to some indie rock. Also super passionate about photography, she loves portraits and wildlife photography – a habit turned love that formed with the amount of traveling she did as a teenager. As a girl who grew up with books and movies like Pride & Prejudice, her love for period fashion is huge. And being curly haired, she’s always on a constant hunt for solutions to problems that come with having ringlets and loves sharing them with people through her articles. For feedback and questions, email [email protected] or connect with her on twitter @ni95.