50 Best Chick Flicks Of All Time

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Movies offer a fun way to escape from the stress and problems of everyday life by submerging your mind into other people’s lives which provides a much-needed distraction in this difficult time of social distancing. 

However, picking a movie can be a long and arduous task though and for some, it can take hours… I would know. With that in mind, I have curated a list of some of the best chick flicks to watch that will make you laugh, cry, debate and fall in love with love. 

Wow. That last line sounded incredibly corny. . . I wouldn’t have it any other way. *Cue the lovebirds flying over a picturesque view*

For some more binge-worthy movies, check out these 20 fun teen movies.

50. Never Been Kissed (1999) 

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Going undercover as a student at her former high school should be easy for the fresh-faced Josie Geller (Drew Barrymore), but things quickly spin out of control when she falls for English teacher Sam Coulson (Michael Vartan).

49. Me Before You (2016) 

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I read the book before seeing the movie, so I thought I would be prepared. Well, I was wrong. Will Traynor and Louisa Clark don’t have the typical love story. It’s the type that’s born from friendship and trust, so of course you’re rooting for them from the get-go, but there’s one problem: Will doesn’t think life is worth living now that he is a paraplegic. What I suggest, read the book before the movie to get the full effect and get ready for the waterworks.

48. Magic Mike (2012) 

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When Magic Mike was released, I remember not being allowed to watch it because it was inappropriate. A few years passed before I finally watched it and, let me say, I felt incredibly cool and adultish viewing it that first time. 

Channing Tatum stars as Mike, a handyman by day and stripper by night, trying desperately to make ends meet. When he sees potential in nineteen-year-old Adam (Alex Pettyfer), he takes him under his wing and teaches him how to to be successful. Everything falls apart though when Mike falls for Adam’s older sister Brooke (Cody Horn) who does not approve of her younger brother’s new lifestyle.

47. How To Be Single (2016) 

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Fresh out of college, Alice (Dakota Johnson) decides it’s time to break up with her boyfriend and takes a job in NYC as a paralegal. Fellow co-worker Robin (Rebel Wilson) takes Alice under her wing and helps her explore the bustling streets of the city that never sleeps where she is free to take advantage of her newfound lifestyle as a single gal.  best chick flicks

46. He’s Just Not That into You (2009)

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He’s Just Not That into You features an all-star cast with many notable favorites: Ben, Affleck, Jennifer Aniston, Drew Barrymore, Jennifer Connelly, Kevin Connolly, Bradley Cooper, Ginnifer Goodwin, Scarlett Johansson and Justin Long. Following the love lives of a group of friends, this funny chick flick explores the complexities of contemporary relationships in all their confusing glory. best chick flicks

45. Grease (1978) 

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Grease is one of my personal favorite musicals, filled with killer songs and unforgettable performances. This 1978 blockbuster follows bad boy Danny Zuko (John Travolta) and good girl Sandy (Olivia Newton John) as they explore their differences and try to find love, but with the T-Birds and Pink Ladies giving their two-cents, it won’t be easy. The ending may be a bit dated depending on how you interpret it, but we’ll always be hopelessly devoted to this classic.

44. Bride Wars (2009) 

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Childhood friends, Liv (Kate Hudson) and Emma (Anne Hathaway) have dreamt about their future weddings being held at the Plaza Hotel since they were young girls. In a twist of fate, Liv and Emma become engaged at the same time. What should be a celebratory time becomes a bridal bloodbath due to a scheduling mishap that results in the two friends’ weddings occurring at the exact same time. best chick flicks

43. Twilight (2008) 

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Twilight brought forth the vampire craze and it became typical to ask friends if they were Team Edward or Team Jacob. To say that Twilight took the world by storm would be an understatement. It even launched the parody movie Vampires Suck.

Bella Swan (Kristen Stewart) moves from the warm and sunny state of Arizona to the cold and dreary town of Forks, Washington to live with her dad. There she meets the allusive and mysterious Edward Cullen (Robert Pattison) who draws Bella in with his sparking personality. When she discovers Edward’s secret, Bella is thrust into a world where mythical creatures exist and vampires are out to get her.  best chick flicks

42. Someone Great (2019) 

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Someone Great may be labeled as a rom-com, but it is so much more than that. Rather, it’s a toast to friendships. When Jenny’s (Gina Rodriguez) longtime boyfriend Nate (Lakeith Stanfield) ends things, she’s heartbroken, lost and unsure of her future. But she’s not alone and with help from her two besties, Blair (Brittany Snow) and Erin (DeWanda Wise), Jenny manages to heal as they go on one last wild adventure in NYC before she moves to San Francisco for a new job as a music journalist. best chick flicks

41. Sleepless in Seattle (1993) 

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After the death of his wife, Sam Baldwin (Tom Hanks) and his son Jonah (Ross Mallinger) pack their things and move to Seattle. One night, Jonah calls into a talk-radio show in hopes of finding a new wife for his father which prompts Sam to get on the line and give his own take on the situation. Surprisingly enough, Baltimore reporter Annie Reed (Meg Ryan) is listening to the station at that moment and falls for him. There’s a few problems with that though: 1) she is engaged and 2) they live on the opposite sides of the country. best chick flicks

40. Freaky Friday (2003) 

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Remakes can be a hit-or-miss. In the case of Freaky Friday, it was definitely a hit. Single mother Tess Coleman (Jamie Lee Curtis) and her teenage daughter Anna (Lindsay Lohan) are constantly at odds with each other. That all changes when they wake up to discover they have somehow switched bodies and are unable to switch back. Along the way, they see a different side of one another and learn that they both have their own set of challenges.  best chick flicks

39. Enchanted (2007) 

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My first memory of Enchanted is when my dad stated, “Wait, this is a cartoon?” That and when I looked over to my dad at the end and saw him tearing up had to be the funniest moments ever during this enchanting movie. best chick flicks

Giselle’s (Amy Adams) plans to marry Prince Edward (James Marsden) are thwarted after his evil stepmother (Susan Sarandon) sends the future princess to New York City, a cold and harsh place compared to the fairytale land of Andalasia. Pessimistic divorce lawyer Robert (Robert Dempsey) comes to Giselle’s rescue and offers her a place to stay. As the days pass, the two become closer, but will true love conquer all? After all, love only exists in fairy tales, right? 

38. Crazy Rich Asians (2018) 

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I don’t even remember how many times I’ve watched Crazy Rich Asians now. It’s probably some inane number. Honestly, if it was on right now I’d definitely watch it. I love this movie. 

Constance Wu and Henry Golding play longtime couple Rachel Chu and Nick Young. When Nick asks Rachel to accompany him to his best friend’s wedding in Singapore, she is more than happy to, not knowing his family’s social and economic status. Imagine her shock when she realizes that Nick is one of the country’s most eligible bachelors. Crazy Rich Asians is a cute and hilarious comedy that will immerse you into a world of backstabbing debutantes, comical friends and eccentric relatives.

37. Sixteen Candles (1984) 

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Directed by John Hughes, Sixteen Candles offers all the 80’s nostalgia in this classic film starring Molly Ringwald who plays an angst-ridden Samantha, experiencing the worst sixteenth birthday when her entire family forgets about said birthday. Add in her longtime crush Jake Ryan (Michael Schoeffling) and you have yourself an entertaining movie with an A-list cast. Still, that doesn’t take away from the problematic and disturbing issues apparent within the film.  best chick flicks

36. To All The Boys I’ve Loved Before (2018) 

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Lana Condor and Noah Centineo star in this 2018 rom-com about Lara Jean, a teenage girl whose five top-secret love letters get mailed to her crushes. When Lara Jean realizes she’s been exposed, her entire world implodes. After all, one of the letters went to her best friend/sister’s boyfriend Josh (Israel Broussard). In the process of avoiding him, Lara Jean becomes closer with one of her past crushes, the popular and seemingly unattainable Peter Kavinsky. What more can you ask for in a teenage romance? best chick flicks

35. Coyote Ugly (2000) 

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Violet Sanford (Piper Perabo) moves to New York with dreams of making it big time as a famous songwriter. When Violet finds herself broke, she is desperate for a job. In a stroke of luck, she lands a gig as a barmaid at the hottest and wildest nightclub in the city, Coyote Ugly.

34. Titanic (1997) 

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Must anything be said about this classic that tells the story of star-crossed lovers Jack (Leonardo DiCaprio) and Rose (Kate Winslet)? The ominous cloud that hangs over the first half of the film has nothing on that iceberg. You know what’s going to happen. No matter how much you hope the Titanic misses it, you know it’s going to happen. Also, anyone who watches Titanic has an opinion on the ending.  best chick flicks

33. P.S. I Love You (2007) 

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Holly and Gerry’s decade-long marriage was as much tender as it was difficult. Knowing that his days were numbered due to a brain tumor, Gerry put together a year’s worth of surprises in hopes of taking Holly on a journey that would help her heal and move on. 

32. Bridget Jones’s Diary (2001) 

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New Year’s is a time of resolutions and Bridget decides it’s time to get her life on track before she becomes a trainwreck. One of Bridget’s high-ranking resolutions involves finding herself a decent man to settle down with. Loosely based on Jane Austen’s Pride and Prejudice, Bridget is caught between the charming and charismatic boss, Daniel Cleaver (Hugh Grant), and the arrogant childhood friend Mark Darcy (Colin Firth).  best chick flicks

31. A Walk to Remember (2002) 

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I’ve seen A Walk to Remember twice now. The first time I didn’t cry. The second time was much different. I’m not sure if I’m getting more emotional with age, but boy was this a tearjerker. For me, the most tear-heavy part wasn’t the end though. It was everything in the middle. Have a box of tissues at hand and maybe a towel. The tissues won’t last forever. best chick flicks

30. Mamma Mia! (2008) 

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Based on the popular Broadway musical, this movie brings forth Amanda Seyfried as 20-year-old Sophie whose wedding day is quickly approaching. Hoping to figure out who her father is, Sophie invites three men from her mother Donna’s (Meryl Streep) past: Sam (Pierce Brosnan), Bill (Stellan Skarsgård) and Harry (Colin Firth). Sophie is set on having one of them walk her down the aisle on her big day, no matter the consequences.   best chick flicks

29. The Sweetest Thing (2002) 

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Christina Applegate, Cameron Diaz and Selma Blair star in this chick flick as besties Courtney, Christina and Jane who are A-okay with their single lifestyle. When Christina meets the nonchalant and not-easily-impressed Peter (Thomas Jane), she thinks he’s the one. With help from Courtney and Jane, they go on a roadtrip with a particular destination in mind: Peter’s brother’s wedding. 

28. She’s the Man (2006) 

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Banned from joining the boys’ soccer team, Viola (Amanda Bynes) poses as her twin brother Sebastian at his new boarding school so she can play soccer. Things become complicated when she falls for her roommate Duke (Channing Tatum), especially when her brother returns sooner than expected only to find his sister pretending to be him. 

27. Sweet Home Alabama (2002) 

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Reese Witherspoon stars as a New York fashion designer who becomes engaged to one of the most eligible bachelors (Patrick Dempsey) in the city. There’s just one big problem that comes in the form of her high school sweetheart Jake (Josh Lucas), the guy she married back in high school who refuses to sign the divorce papers.  

26. Confessions of a Shopaholic (2009) 

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This 2009 romantic comedy is based on Sophie Kinsella’s Shopaholic series that tells the story of Rebecca Bloomwood (Isla Fisher), a New York City girl who loves to shop… too much. When she realizes that she’s drowning in debt, she must learn how to cut back on her spending habits. What better way to do that than become an advice columnist for a financial magazine. 

25. Breakfast at Tiffany’s (1961) 

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This iconic classic tells the story of Holly Golightly (Audrey Hepburn), a young woman set on scoring an older rich man leading her to work as an escort and her upstairs neighbor, a New York writer dating an older wealthy woman.  

24. A Cinderella Story (2004) 

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A Cinderella Story is one of my favorite adaptations of the classic tale of Cinderella. Hilary Duff reprises the role of Sam (aka Cinderella) in this modern take of the well-known tale and her Prince Charming comes in the form of Austin Ames (Chad Michael Murray), the most popular boy in school.

23. Romy and Michele’s High School Reunion (1997) 

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Ten years after their high school graduation, Romy (Mira Sorvino) and Michele (Lisa Kudrow) have yet to reach their goals in their personal and professional lives. When they hear about their upcoming high school reunion, these best friends decide it’s time to show their classmates how much they have changed by cooking up a lie that eventually spirals out of control.

22. When Harry Met Sally (1989) 

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Billy Crystal and Meg Ryan play two friends, Harry and Sally, who wonder if it’s truly possible for men and women to be friends who are purely platonic, without wanting to have sex. The real question is whether that’s possible for Harry and Sally.

21. How to Lose a Guy in 10 Days (2003) 

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Kate Hudson and Matthew McConaughey star in this chick flick about an advice columnist who plans to write a piece regarding how to get a man to leave you in 10 days. To test out this theory, Andie enlists executive Ben Berry who thinks he can do just the opposite by making any woman fall in love with him in the same number of days.   

20. Bring It On (2000) 

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Kristin Dunst and Gabrielle Union face off in this iconic cheerleader movie. The Toro cheerleading squad from Rancho Carne High School plan to bring home the national championship trophy for the sixth year in a row, but Torrance’s plans are put in jeopardy when she realizes the routines were stolen from Clover, their competition. If you’re looking for a fun and light sports comedy that doesn’t take itself too seriously, Bring It On is the perfect option.

19. 50 First Dates (2004) 

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This 2004 funny chick flick features Adam Sandler as Henry Roth, a man set on wooing Lucy (Drew Barrymore) who suffers from a type of short-term memory loss where she forgets everything that happened the day before. Because of her memory loss, Henry is forced to win Lucy over every single day which creates an interesting and entertaining storyline for viewers.

18. 27 Dresses (2008) 

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Wedding after wedding after wedding… Jane (Katherine Heigl) is a serial bridesmaid, making her the ultimate wedding guru. When her sister Tess (Malin Akerman) lands Jane’s long-time crush George (Edward Burns), she finds herself questioning everything as her world seemingly implodes, especially with the cute reporter Kevin (James Marsden) who is determined to get the dirt on Jane’s unique journey; always the bridesmaid and never the bride. 

17. Pretty Woman (1990) 

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In this modern retelling of Cinderella, wealthy businessman Edward (Richard Gere) picks up sex worker Vivian (Julia Roberts) while on a business trip. During their time together, they slowly fall for each other as they realize there is more to each other than their initial first impressions. As the film that launched Robert’s career, this is most certainly a must-see chick flick.

16. 13 Going On 30 (2004) 

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The old adage saying be careful what you wish for is true for 13-year-old Jenna (Jennifer Garner) after a wish turns her into a 30-year-old woman. Skipping adolescence may sound glamorous as a teen, but Jenna soon learns that it’s not all sunshine and rainbows. This heartwarming film is the perfect blend of romance, comedy, and a dash of fantasy. And you’ll probably want to try some razzles by the end. 

15. Love, Actually (2003) 

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Love, Actually follows multiple storylines during the Christmas season as they deal with their love lives. Over the years, it has garnered much attention which has created quite the divide between people who love it or hate it.

14. Dirty Dancing (1987) 

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A coming-of-age film that launched the iconic quote, “Nobody puts Baby in a corner.” During one summer in the 60’s at a resort in the Catskills, Baby (Jennifer Grey) finds herself falling for the resort’s dance instructor Johnny (Patrick Swayze) after he recruits her to become his new dance partner. When her father finds out though, all hell breaks loose.

13. Easy A (2010) 

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For an entertaining retelling of The Scarlet Letter, Easy A has you covered. Deemed the school slut after allegedly sleeping with a fellow classmate, Olive (Emma Stone) is shunned by her peers and loses her best friend in the process. As her life falls apart, Olive decides to live up to her newfound title by dressing and acting the part. Filled with laughs, humor, and a brilliant cast, you’ll undoubtedly enjoy this satirical film.

12. The Proposal (2009) 

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The Proposal is another fun Sandra Bullock chick flick. This time around, Bullock stars as Margaret Tate, a prosperous book editor who has reinvented herself as a strict and domineering boss in order to be taken seriously as a leader. When she is faced with deportation to Canada, Margaret says she is engaged to her assistant Andrew Paxton (Ryan Reynolds) which puts them into a sticky situation that involves a trip to Andrew’s family home in Alaska.

11. Miss Congeniality (2000) 

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Sandra Bullock stars as a FBI agent who goes undercover as a participant in the Miss United States beauty pageant when a serial bomber drops a hint that a contestant may be their next target. Completely out of her element as a contestant, Grace must successfully navigate life as a beauty pageant contestant in order to catch the bomber before it’s too late.

10. The Devil Wears Prada (2006) 

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The Devil Wears Prada is a classic with a star-studded cast: Meryl Streep, Anne Hathaway and Emily Blunt to name a few. Fresh out of college, Andy lands a job at a prestigious Runway magazine, but finds herself stressed and overworked because of her boss Miranda Priestly. Giving an inside look into the fashion industry, The Devil Wears Prada is a must-watch. 

9. Crazy, Stupid, Love (2011)

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When Cal Weaver (Steve Carell) learns of his wife’s (Julianne Moore) infidelity and future plans of divorce, his perfect life takes a nosedive and puts him on a tailspin that involves getting advice from player extraordinaire Jacob Palmer (Ryan Gosling) who teaches Cal how to successfully navigate the dating world whilst Jacob finds himself slowly falls for recent law school graduate Hannah (Emma Stone). 

8. Pitch Perfect (2012)

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College music competitions have never been more serious. College student Beca (Anna Kendrick) never imagined becoming a part of a clique, but that all changes when she finds herself joining the Bellas, an acapella singing group. Each character brings something fun to the table which makes this all the more entertaining for viewers. The best part of Pitch Perfect is undoubtedly the catchy songs and exciting performances.  

7. The Notebook (2004) 

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The Notebook is the ultimate tear-jerker and anyone who says otherwise is a robot (I have to say, I was once in the latter group). This film tells the story of rich girl Allie (Rachel McAdams) and Noah Calhoun (Ryan Gosling) who’s from the wrong side of the tracks according to Allie’s parents. The love that exists between the two never dies which makes their story even more gut-wrenching, yet beautiful. Make sure you have a box of tissues on hand during this sobfest. 

6. The Princess Diaries (2001) 

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Anne Hathaway stars as Mia Thermopolis, an introverted teenager whose entire world is tipped off its axis when she learns she is the heir to the throne in the small country of Genovia. The road to becoming a princess is not easy however, especially when her no-nonsense grandmother, Queen Clarisse Renaldi (Julie Andrews), shows up to teach Mia how to be a princess.

5. 10 Things I Hate About You (1999) 

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This modern adaption of Shakespeare’s The Taming of the Shrew is the ultimate retelling featuring Julia Stiles and Heath Ledger. This version revolves around the sarcastic and critical high school senior Kat Stratford and the new dark and mysterious student Patrick Verona. Seeing Heath Ledger sing “Can’t Take My Eyes Off You” is iconic and the moment when Kat reads her poem will move you beyond words.

4. Clueless (1995) 

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This 1995 film centers around the shallow and rich teen Cher (Alicia Silverstone) who is at the top of the food chain at her Beverly Hills high school. After giving the helplessly klutzy new student Tai (Brittany Murphy) a makeover, she climbs the social ladder and becomes Queen B which leads Cher to realize that her ex-step-brother Josh (Paul Rudd) was right about her shallow outlook on life and you know what happens next (*wink wink*). “Ugh, as if.”

3. Legally Blonde (2001) 

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Legally Blonde stars Reese Witherspoon as Elle Woods, a blonde sorority girl who challenges all stereotypes when she is admitted into Harvard Law School to win back her ex-boyfriend Warner (Matthew Davis). When Elle realizes how Warner views her, she is determined to prove everyone wrong by succeeding and she does so with determination, integrity and style.   best chick flicks

2. Bridesmaids (2011) 

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“Help me, I’m poor.” “Why can’t you just be happy for me and then go home and talk behind my back later like a NORMAL PERSON!?” “I just took a s**t in the middle of the street.”

Annie (Kristen Wiig) and Lillian (Maya Rudolph) have been childhood friends since forever. When Lillian announces she’s engaged, Annie is happy to be her maid of honor. At the same time, she is filled with insecurities when she realizes Lilliana is moving in a new direction while she has remained frozen in time. From there, Lillian and her bridesmaid gang go on a journey of self-discovery that is as comical as it is heartwarming. This 2011 comedy is ultra quotable and filled to the brim with hilarious moments that are guaranteed to crack you up. 

1. Mean Girls (2004) 

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You go Glen Coco!” “On Wednesdays we wear pink.” “That’s so fetch.” “Get in loser, we’re going shopping.” If we looked at iconic quotes alone, Mean Girls would be at the top of the list. And you can’t say we didn’t learn anything; I mean, we will forever remember that the limit does not exist.