Nostalgic Romance: Best Chick Flicks Of The 90s & 2000s

The 90s and 2000s delivered an array of iconic romantic comedies perfect for a girls' night in or cozying up for a date night. These nostalgic chick flicks captured the era's fashion and pop culture zeitgeist while tugging at our heartstrings. From classic teen romances to witty romantic satires, these are the best chick flicks to revisit from the 90s and 2000s.

Get ready for a major dose of nostalgia! This list of 25 romantic comedies 90s and 2000s will remind you of young love and coming-of-age while revisiting laugh-out-loud funny, feel-good stories. You'll swoon over dreamy leading men and empowered female characters. These timeless chick flicks still resonate today with wit, charm and wisdom about relationships that endure the test of time.

But before going into details of each movie separately, we have compiled these movies in the following table. You can jump to any movie details by clicking its name from the following table.

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1 - Angus (1995)

• All Cast: Charlie Talbert (Angus Bethune), George C. Scott (Grandpa Ivan), Kathy Bates (Ms. Struvie), Ariana Richards (Melissa Lefevre), James Van Der Beek (Rick Sanford), Chris Owen (Troy Wazenegger), Rita Moreno (rachele), Jennifer Soo Scott (Freida), Conor Moran (Billy), Allyn Dow (smitty)
• Director: Patrick Read Johnson
• Release Date: September 15, 1995
• IMDb Rating: 6.7
• Run Time: 89 minutes
• Where to Watch: Amazon Prime Video, TUBI

Angus is a 1995 American coming-of-age comedy film directed by Patrick Read Johnson and starring Charlie Talbert and George C. Scott. Angus Bethune is a teenage outcast who copes with ridicule over his size by relying on humor and help from his grandfather. When a popular cheerleader surprisingly reaches out with kindness towards Angus, he strives for self-acceptance and to find the courage to pursue his crush.

This heartwarming underdog story explores themes of bullying, body image, and overcoming challenges in high school. Talbert gives a smart, empathetic performance as the titular character. While predictable at times, Angus still remains relevant with an uplifting message about being yourself. It serves as a humorous yet thoughtful period time capsule of 1990s high school.

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2 - Clueless (1995)

• All Cast: Alicia Silverstone (Cher Horowitz), Stacey Dash (Dionne Davenport), Brittany Murphy (Tai Frasier), Paul Rudd (Josh Lucas), Donald Faison (Murray Duvall), Elisa Donovan (Amber Mariens), Wallace Shawn (Mr. Hall), Twink Caplan (Ms. Geist), Jeremy Sisto (Elton Tiscia), Breckin Meyer (Travis Birkenstock)
• Director: Amy Heckerling
• Release Date: July 19, 1995
• IMDb Rating: 6.9
• Run Time: 97 minutes
• Budget: $12 million
• Revenue: $56.6 million
• Where to Watch: Paramount+, Amazon Prime Video

Clueless is a 1995 American coming-of-age teen comedy film written and directed by Amy Heckerling. Loosely based on Jane Austen's Emma, it follows wealthy, popular high school student Cher (Alicia Silverstone) who plays matchmaker for teachers and classmates in Beverly Hills. But she finds herself falling for her former stepbrother (Paul Rudd).

With charming performances and witty dialogue, Clueless became one of the decade's most iconic teen films. Silverstone shines as the sweetly oblivious Cher, delivering hilarious misadventures in romance, friendship, and self-discovery. The film affectionately satirizes 90s fashion and slang while proving Jane Austen's stories translate seamlessly to modern Beverly Hills.

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3 - Romeo + Juliet (1996)

• All Cast: Leonardo DiCaprio (Romeo), Claire Danes (Juliet), John Leguizamo (Tybalt), Harold Perrineau (Mercutio), Pete Postlethwaite (Father Laurence), Paul Sorvino (Fulgencio Capulet), Brian Dennehy (Ted Montague), Diane Venora (Gloria Capulet), Paul Rudd (Dave Paris), Vondie Curtis-Hall (Captain Prince)
• Director: Baz Luhrmann
• Release Date: November 1, 1996
• IMDb Rating: 6.7
• Run Time: 120 minutes
• Budget: $14.5 million
• Revenue: $147.5 million
• Where to Watch: Disney+ Hotstar

Romeo + Juliet is a 1996 romantic drama directed by Baz Luhrmann. It reimagines Shakespeare's classic in a stylized modern setting. Leonard DiCaprio and Claire Danes portray the iconic star-crossed lovers, speaking in Shakespearean dialogue amid contemporary backdrops.

Luhrmann's signature colorful, eclectic flair gives this adaptation a vibrant cinematic energy. Though it divided critics, Romeo + Juliet resonated with young audiences through its verve, passion and edgy updating of the timeless tragedy. DiCaprio and Danes' talent and chemistry help translate the Bard for 90s teens.

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4 - Edge of Seventeen (1998)

• All Cast: Chris Stafford (Eric Hunter), Tina Majorino (Maggie), Lea DeLaria (Ms. Crowe), Jessica Bowman (Sandra), Eddie Kaye Thomas (Rod), Jason Cermak (Aaron), Greg Kean (Mr. Mathews), Julie Ann Johnson (Mrs. Mathews), Andy Stahl (Mr. Hunter), Lesley Gerza (Mrs. Hunter)
• Director: David Moreton
• Release Date: June 16, 1998
• IMDb Rating: 6.8
• Run Time: 104 minutes
• Where to Watch: DVD, iTunes

Edge of Seventeen is a 1998 coming-of-age dramedy film set in small-town Ohio circa 1984. It centers on closeted teenager Eric (Chris Stafford) navigating high school and grappling with his sexual orientation as he develops feelings for a male classmate.

Director David Moreton and writer Todd Stephens craft a poignant, honest look at the struggles of coming out in 1980s America through Eric's experiences. While touching on homophobia, it also stresses the importance of being accepted for who you are. With relatable adolescent characters and bittersweet humor, it captures a tender, introspective perspective on LGBTQ youth.

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5 - Drive Me Crazy (1999)

• All Cast: Melissa Joan Hart (Nicole Maris), Adrian Grenier (Chase Hammond), Stephen Collins (Ray Maris), Mark Metcalf (Mr. Hammond), Ali Larter (Dulcie), Timothy Bottoms (Harry Maris), Gloria Votsis (Beth), Matthew Nessan (Toby), Timothy Olyphant (Kirk), Kylie Sparks (Tara)
• Director: John Schultz
• Release Date: October 1, 1999
• IMDb Rating: 5.9
• Run Time: 91 minutes
• Budget: $10 million
• Revenue: $17.9 million
• Where to Watch: Hulu, Amazon Prime Video

Drive Me Crazy is a 1999 teen romantic comedy starring Melissa Joan Hart and Adrian Grenier. Nicole and Chase, neighbors who can't stand each other, grudgingly agree to pretend to date in hopes of making their exes jealous. But spending time together leads to sparks between the oddball opposites.

With amusing antagonism between the leads, Drive Me Crazy puts a playful spin on the fake dating trope. Grenier and Hart's quirky chemistry and satirical tone of 1999 trends makes this Y2K rom-com a nostalgic capsule of its era.

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6 - Never Been Kissed (1999)

• All Cast: Drew Barrymore (Josie Geller), David Arquette (Rob Geller), Michael Vartan (Sam Coulson), Molly Shannon (Anita), Leelee Sobieski (Aldys), Jessica Alba (Kirsten), Marley Shelton (Kristen), James Franco (Jason), Giuseppe Andrews (Billy), Jeremy Jordan (Guy Perkins)
• Director: Raja Gosnell
• Release Date: April 9, 1999
• IMDb Rating: 6.0
• Run Time: 107 minutes
• Budget: $25 million
• Revenue: $84.4 million
• Where to Watch: Hulu

Never Been Kissed is a 1999 rom-com starring Drew Barrymore as Josie Geller, a newspaper reporter who goes undercover at a high school. Assigned to research teen culture, Josie revives her own traumatic high school memories and falls for teacher Sam (Michael Vartan).

While predictable, Barrymore's goofy, awkward performance ensures its eccentricities entertain. Her chemistry with cool teacher Vartan made this one of the era's popular fantasies. Never Been Kissed affectionately spoofs high school stereotypes through an outsider's comedic lens.

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7 - Notting Hill (1999)

• All Cast: Julia Roberts (Anna Scott), Hugh Grant (William Thacker), Rhys Ifans (Spike), Emma Chambers (Honey Thacker), James Dreyfus (Martin), Dylan Moran (Rufus the Thief), Roger Frost (Anton Skinner), Tim McInnerny (Max), Gina McKee (Bella), Hugh Bonneville (Bernie)
• Director: Roger Michell
• Release Date: May 28, 1999
• IMDb Rating: 7.1
• Run Time: 124 minutes
• Budget: $42 million
• Revenue: $364 million
• Where to Watch: HBO Max

Notting Hill follows Anna (Julia Roberts), an American movie star who crosses paths with William (Hugh Grant), a quirky, charming London bookshop owner. After a rocky start, the mismatched pair begins dating amidst clashing of celebrity and ordinary lives.

Carried by affable star power from Roberts and Grant, this Working Title rom-com became a global hit for its fairy tale premise. Though fantastical, Notting Hill mines humor and emotion from the brittle vulnerability behind fame. Crackling chemistry and romcom magic made this a much-loved fantasy of intersecting worlds.

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8 - 10 Things I Hate About You (1999)

• All Cast: Heath Ledger (Patrick Verona), Julia Stiles (Kat Stratford), Joseph Gordon-Levitt (Cameron James), Larisa Oleynik (Bianca Stratford), David Krumholtz (Michael Eckman), Andrew Keegan (Joey Donner), Gabrielle Union (Chastity Church), Larry Miller (Walter Stratford), Allison Janney (Ms. Perky), Daryl Mitchell (Mr. Morgan)
• Director: Gil Junger
• Release Date: March 31, 1999
• IMDb Rating: 7.3
• Run Time: 97 minutes
• Budget: $16 million Revenue: $53.5 million
• Where to Watch: Disney+ Hotstar

10 Things I Hate About You is a 1999 teen rom-com that reimagines The Taming of the Shrew in a late 90s high school setting. Julia Stiles stars as strong-willed feminist Kat, who must date the rebellious Patrick (Heath Ledger) so her younger sister can date his friend.

With breakthrough performances from Ledger and Stiles, the film brought Shakespeare to life through a sharp script that affectionately satirized high school politics and divides. The chemistry between leads made this modern classic teen romance touch on deeper themes of acceptance, family, and being true to yourself.

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9 - Cruel Intentions (1999)

• All Cast: Sarah Michelle Gellar (Kathryn Merteuil), Ryan Phillippe (Sebastian Valmont), Reese Witherspoon (Annette Hargrove), Selma Blair (Cecile Caldwell), Louise Fletcher (Helen Rosemond), Joshua Jackson (Blaine Tuttle), Eric Mabius (Greg McConnell), Sean Patrick Thomas (Ronald Clifford), Christine Baranski (Bunny Caldwell), Swoosie Kurtz (Dr. Greenbaum)
• Director: Roger Kumble
• Release Date: March 5, 1999
• IMDb Rating: 6.8
• Run Time: 97 minutes
• Budget: $10–11 million
• Revenue: $75 million
• Where to Watch: Amazon Prime Video

Cruel Intentions is a 1999 American teen romantic drama that reimagines the 1782 novel Les Liaisons dangere uses in modern New York City. Wealthy, popular step-siblings Kathryn (Sarah Michelle Gellar) and Sebastian (Ryan Phillippe) manipulate their classmates through sexual mind games.

This risqué cult film packs in sinful melodrama through its beautiful, manipulative leads. However, the cruelty of their wagers gets challenged when real feelings emerge. Phillippe and Gellar's combustible pairing delivered intoxicating teen noir, even if the camp goes over-the-top. The film gained notoriety for exploring risqué themes through a youthful lens.

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10 - Bring It On (2000)

• All Cast: Kirsten Dunst (Torrance Shipman), Eliza Dushku (Missy Pantone), Jesse Bradford (Cliff Pantone), Gabrielle Union (Isis), Clare Kramer (Courtney), Nicole Bilderback (Whitney), Tsianina Joelson (Darcy), Rini Bell (Kasey), Nathan West (Jan), Holmes Osborne (Coach Sparky Polk)
• Director: Peyton Reed
• Release Date: August 25, 2000
• IMDb Rating: 6.1
• Run Time: 98 minutes
• Budget: $11 million
• Revenue: $90 million
• Where to Watch: Hulu

Bring It On is a 2000 cheerleading comedy film starring Kirsten Dunst and Eliza Dushku. Head cheerleader Torrance (Dunst) discovers her squad's routines were stolen from a hip-hop crew. She must lead her team to devise an original performance to compete.

With spectacular cheer sequences, this vibrant teen comedy made cheerleading cinematic. Beyond the pep, it showcases themes of friendship, ethics, sportsmanship and embracing your own style. Dunst's endearing performance and infectious spirit anchored this crowd-pleasing underdog adventure.

11 - Save the Last Dance (2001)

• All Cast: Julia Stiles (Sara Johnson), Sean Patrick Thomas (Derek Reynolds), Kerry Washington (Chenille Reynolds), Fredro Starr (Malakai), Terry Kinney (Roy Johnson), Bianca Lawson (Nikki), Vince Green (Snookie), Garland Whitt (Willie), Mirron Willis (P.J.), Gabe Ruskin (Guy in the hallway)
• Director: Thomas Carter
• Release Date: January 12, 2001
• IMDb Rating: 6.2
• Run Time: 112 minutes
• Budget: $13 million
• Revenue: $131.4 million
• Where to Watch: Paramount+

Save the Last Dance follows gifted ballet dancer Sara (Julia Stiles) who moves to Chicago after her mother dies and struggles to fit in at her new inner-city high school. She befriends Derek (Sean Patrick Thomas) who introduces her to hip-hop and helps prepare her Julliard audition.

Though formulaic, Save the Last Dance was celebrated for showcasing modern African-American youth culture through its interracial romance. Beyond melodrama, it insightfully handled themes of grief, gang violence, finding passion, and prejudice. The leads' chemistry and youthful spirit gave this crowd-pleaser heart.

12 - The Princess Diaries (2001)

• All Cast: Anne Hathaway (Mia Thermopolis), Julie Andrews (Queen Clarisse Renaldi), Héctor Elizondo (Joe), Heather Matarazzo (Lilly Moscovitz), Robert Schwartzman (Michael Moscovitz), Caroline Goodall (Helen Thermopolis), Erik von Detten (Josh Bryant), Patrick Flueger (Jeremiah Hart), Sean O'Bryan (Patrick O'Connell), Sandra Oh (Vice Principal Gupta)
• Director: Garry Marshall
• Release Date: August 3, 2001
• IMDb Rating: 6.3
• Run Time: 115 minutes
• Budget: $26 million
• Revenue: $165.3 million
• Where to Watch: Disney+ Hotstar

The Princess Diaries follows Mia Thermopolis (Anne Hathaway), an awkward teenager who learns she is heir to the throne of the fictional European kingdom Genovia. Julie Andrews plays her royal grandmother, Queen Clarisse, who aims to groom Mia into a princess.

Carried by Andrews' legendary charm and wit, this coming-of-age comedy made Hathaway a star. With a script that balances earnestness and self-awareness, it remains one of the most winning modern-day princess tales. The Princess Diaries highlights that being yourself is most important, regardless of titles or looks.

13 - Get Over It (2001)

• All Cast: Kirsten Dunst (Kelly Woods), Ben Foster (Berke Landers), Melissa Sagemiller (Allison McAllister), Shane West (Striker), Colin Hanks (Dennis Wallace), Sisqó (Dennis Wallace), Vivica A. Fox (Dr. Monet), Martin Short (Dr. Desmond Forrest Oates), Carmen Electra (Mistress Moira), Mila Kunis (Basil)
• Director: Tommy O'Haver
• Release Date: March 9, 2001
• IMDb Rating: 5.8
• Run Time: 87 minutes
• Budget: $22 million
• Revenue: $19.5 million
• Where to Watch: HBO Max

Get Over It is a 2001 American teen comedy loosely based on Shakespeare's A Midsummer Night's Dream. When Berke (Ben Foster) gets dumped by Allison (Melissa Sagemiller) for Striker (Shane West), he tries to win Allison back by joining the school play also featuring his friends and exes.

The goofy fairytale satire showcases its young cast who clearly relish sending up high school romance. Sprinkled with cheerful musical numbers, Get Over It embraces absurdity and fun over heavy lessons. Cameos by early 2000s celebrities like Kirsten Dunst add to the playfulness.

14 - Bend It Like Beckham (2002)

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• All Cast: Parminder Nagra (Jess Bhamra), Keira Knightley (Juliette "Jules" Paxton), Jonathan Rhys Meyers (Joe), Anupam Kher (Mohammad "Mr." Bhamra), Shaheen Khan (Paula Paxton), Archie Panjabi (Pinky Bhamra), Shaznay Lewis (Mel), Frank Harper (Alan Paxton), Juliet Stevenson (Paula Paxton), Ameet Chana (Tony)
• Director: Gurinder Chadha
• Release Date: March 12, 2002
• IMDb Rating: 6.6
• Run Time: 112 minutes
• Budget: $6 million
• Revenue: $76.6 million
• Where to Watch: Disney+ Hotstar

Bend it Like Beckham follows the daughter of traditional Punjabi Sikhs in London who dreams of playing football professionally but is forbidden by her parents. After joining a local women's team, she bonds with her coach and teammate Jules (Keira Knightley).

Touching on multicultural themes through friendship and sport, this feel-good comedy drama was a sleeper hit for its culture-clash underdog story. With heartwarming appeal, it celebrates girl power and pursuing passion against cultural barriers.

15 - A Walk to Remember (2002)

• All Cast: Mandy Moore (Jamie Sullivan), Shane West (Landon Carter), Daryl Hannah (Cynthia Carter), Peter Coyote (Reverend Sullivan), Lauren German (Belinda), Clayne Crawford (Dean), Al Thompson (Eric), Paz de la Huerta (Tracie), Jonathan Parks Jordan (Walker), Matt Lutz (Clay)
• Director: Adam Shankman
• Release Date: January 25, 2002
• IMDb Rating: 7.4
• Run Time: 101 minutes
• Budget: $12 million
• Revenue: $47.5 million
• Where to Watch: Amazon Prime Video

A Walk to Remember is a coming-of-age romance based on the Nicholas Sparks novel. Bad boy Landon (Shane West) falls for Jamie (Mandy Moore), a minister's daughter battling leukemia who helps him become a better person.

Moore and West's gentleness makes this bittersweet teenage love story affecting, if predictable. Their chemistry brings sincerity to the serious themes of terminal illness, faith, and redemption. A Walk to Remember tugged heartstrings through innocent romance and an uplifting message about living life fully.

16 - How to Deal (2003)

• All Cast: Mandy Moore (Halyen "Haley" Fitzgerald), Allison Janney (Lydia Martin), Trent Ford (Macon Forrester), Alexandra Holden (Ashley), Dylan Baker (Ryan), Nina Foch (Grammie), Peter Gallagher (Mr. McConkey), Mackenzie Astin (Grant Spofford), LaDell Preston (Mike), Ivana Milicevic (Tara Reid)
• Director: Clare Kilner
• Release Date: August 8, 2003
• IMDb Rating: 5.7
• Run Time: 103 minutes
• Budget: $15 million
• Revenue: $14.3 million
• Where to Watch: Tubi, Pluto TV

How to Deal follows teenager Halley (Mandy Moore) as she navigates life and love. Her relationships with her musician boyfriend and local DJ force Halley to figure out what’s truly important.

While predictable, Moore's earnest charm makes this a passable coming-of-age story. The characters lack depth, but it captures central teen experiences around family, romance, loss and identity with humor and wisdom. How to Deal touches on the rewards of being your true self.

17 - What a Girl Wants (2003)

• All Cast: Amanda Bynes (Daphne Reynolds), Colin Firth (Henry Dashwood), Kelly Preston (Libby Reynolds), Oliver James (Ian Wallace), Christina Cole (Clarissa Payne-Cartwright), Jonathan Pryce (Alistair Payne), Eileen Atkins (Jocelyn Dashwood), Anna Chancellor (Alicia Wallace), Tom Ellis (Carlo), Vanessa Lee Chester (Rae)
• Director: Dennie Gordon
• Release Date: April 4, 2003
• IMDb Rating: 5.8
• Run Time: 105 minutes
• Budget: $25 million
• Revenue: $50.7 million
• Where to Watch: Showtime, Hulu

What a Girl Wants stars Amanda Bynes as American teenager Daphne, who travels to England to find the father she's never met, a wealthy politician running for office. She disrupts his life while finding true friendship and learning how to be herself.

While formulaic, this lighthearted cross-culture romance was carried by Bynes' energetic charm and lovable kookiness. The contrast between her bubbly personality against a posh British backdrop adds enjoyable humor and clashing sensibilities.

18 - Love Actually (2003)

• All Cast: Hugh Grant (The Prime Minister), Martine McCutcheon (Natalie), Liam Neeson (Daniel), Laura Linney (Sarah), Colin Firth (Jamie), Emma Thompson (Karen), Alan Rickman (Harry), Keira Knightley (Juliet), Bill Nighy (Billy Mack), Rowan Atkinson (Rufus), Thomas Sangster (Sam)
• Director: Richard Curtis
• Release Date: November 7, 2003
• IMDb Rating: 7.0
• Run Time: 135 minutes
• Budget: $45 million
• Revenue: $248.4 million
• Where to Watch: Amazon Prime Video

Love Actually follows the lives of eight very different couples dealing with their love lives during the frantic month before Christmas in London. The Prime Minister falls for his catering staff member, a widower struggles with his love for his deceased wife, a writer falls for his Portuguese housekeeper, a man pursues his lifelong crush on his best friend's new wife, a movie body double has feelings for an actress, a new couple get pressured by their families, a rock star tries to rekindle his fading career, and a young boy pursues the girl of his dreams. Despite the obstacles, love actually is all around for the characters.

19 - A Cinderella Story (2004)

• All Cast: Hilary Duff (Sam), Chad Michael Murray (Austin), Jennifer Coolidge (Fiona), Regina King (Rhonda), Julie Gonzalo (Shelby), Madeline Zima (Brianna), Andrea Avery (Gabriella), Mary Pat Gleason (Eleanor), Paul Rodriguez (Bobby)
• Director: Mark Rosman
• Release Date: July 16, 2004
• IMDb Rating: 5.9
• Run Time: 95 minutes
• Budget: $19 million
• Revenue: $70.1 million
• Where to Watch: Amazon Prime Video

A Cinderella Story is a modern retelling of the classic fairy tale. Sam Montgomery is a teenage girl who is forced to work as a diner waitress by her evil stepmother Fiona and stepsisters Brianna and Gabriella after her father dies. Sam has a secret pen pal named Nomad that she plans to meet at the Halloween dance.

Nomad turns out to be Austin, the popular quarterback that Sam has had a crush on. With the help of her best friend Carter, Sam gets a makeover and dresses up to meet Austin at the dance. However, she must get back before midnight to avoid being caught by Fiona.

20 - The Prince & Me (2004)

• All Cast: Julia Stiles (Paige), Luke Mably (Eddie), Ben Miller (Colin), Miranda Richardson (Queen Rosalind), Eliza Bennett (Olivia), James Fox (King Harald), Alberta Watson (Ruby), John Bourgeois (Frank)
• Director: Martha Coolidge
• Release Date: March 28, 2004
• IMDb Rating: 5.9
• Run Time: 111 minutes
• Budget: $25 million
• Revenue: $42.5 million
• Where to Watch: Paramount+

The Prince & Me follows Paige, a pre-med student at the University of Wisconsin who meets and falls in love with a handsome guy named Eddie who is actually the crown prince of Denmark named Edvard. Paige initially rejects Eddie for lying about his identity but eventually travels to Denmark to be with him.

She struggles to adjust to royal life and Eddie's duties. Paige helps Eddie stand up to his family and embrace his role as future king on his own terms. Their love prevails despite their very different backgrounds.

21 - John Tucker Must Die (2006)

• All Cast: Jesse Metcalfe (John Tucker), Sophia Bush (Beth), Ashanti (Heather), Arielle Kebbel (Carrie), Brittany Snow (Kate), Jenny McCarthy (Lori), Fatso-Fasano (Scott)
• Director: Betty Thomas
• Release Date: July 28, 2006
• IMDb Rating: 5.8
• Run Time: 89 minutes
• Budget: $18 million
• Revenue: $68.8 million
• Where to Watch: HBO Max

John Tucker Must Die follows a serial cheater named John Tucker who dates three different girls secretly at the same time - head cheerleader Beth, activist Heather, and shy Kate. The girls find out about each other and band together to get revenge. They recruit pretty but rebellious Carrie to seduce John and break his heart. Their plan works but not everything goes smoothly. The girls learn about embracing their true selves and gaining self-respect in relationships.

22 - Step Up (2006)

• All Cast: Channing Tatum (Tyler), Jenna Dewan (Nora), Mario (Miles), Drew Sidora (Lucy), Rachel Griffiths (Director Gordon), Damaine Radcliff (Mac Carter)
• Director: Anne Fletcher
• Release Date: August 11, 2006
• IMDb Rating: 6.5
• Run Time: 104 minutes
• Budget: $12 million
• Revenue: $114.2 million
• Where to Watch: Amazon Prime Video

Step Up follows Tyler Gage, a troubled kid from the wrong side of Baltimore who ends up sentenced to community service at the Maryland School of the Arts. There he meets and connects with Nora, a senior dance student who needs a partner for her senior showcase. Tyler has a raw dance talent that pairs well with Nora's technical skills. They begin training in secret against Nora's father's wishes to perform in the showcase and bring their passions together through dance.

23 - Keith (2008)

• All Cast: Jessie Heller (Natalie), Elisabeth Harnois (Brooke), Margo Harshman (Heather), Ignacio Serricchio (Raffael), Jennifer Grey (Jennifer), Michael O'Keefe (Mr. Anderson)
• Director: Todd Kessler
• Release Date: September 19, 2008 (USA)
• IMDb Rating: 7.4
• Run Time: 93 minutes
• Where to Watch: Tubi

Keith is a romantic drama about 17-year-old Natalie who starts dating a guy named Keith. But she soon discovers Keith is not a normal boyfriend - he has terminal cancer. Natalie falls for Keith anyway and struggles with continuing the relationship knowing he will die soon.

She reaches out to help other people with cancer. Keith teaches Natalie to live life to the fullest during the time he has left. They share a bond through their edgy sense of humor about his illness.

24 - Angus, Thongs And Perfect Snogging (2008)

• All Cast: Georgia Groome (Georgia), Aaron Taylor-Johnson (Robbie), Karen Taylor (Lindsay), Alan Davies (Mr Nicolson), Eleanor Tomlinson (Jas), Manjeeven Grewal (Jas), Georgia Henshaw (Ellen), Kimberley Nixon (Wet Lindsay)
• Director: Gurinder Chadha
• Release Date: July 25, 2008
• IMDb Rating: 6.3
• Run Time: 91 minutes
• Budget: $10 million
• Revenue: $13.5 million
• Where to Watch: Tubi

Angus, Thongs and Perfect Snogging is a coming-of-age story about a 14-year-old girl named Georgia Nicolson dealing with friends, family, school, and boys in England. Georgia dreams of having her first kiss with the handsome Robbie that she has a crush on. She tries to give herself a makeover and overhauls her image to get his attention.

Georgia also deals with drama among her friends. She finally gets her first kiss with Robbie at the end but realizes it didn't feel as magical as she imagined. Georgia learns to be comfortable in her own skin.

25 - 500 Days of Summer (2009)

• All Cast: Joseph Gordon-Levitt (Tom), Zooey Deschanel (Summer), Geoffrey Arend (McKenzie), Chloë Grace Moretz (Rachel), Matthew Gray Gubler (Paul), Clark Gregg (Vance)
• Director: Marc Webb
• Release Date: July 17, 2009
• IMDb Rating: 7.7
• Run Time: 95 minutes
• Budget: $7.5 million
• Revenue: $60.7 million
• Where to Watch: Amazon Prime Video

500 Days of Summer follows Tom, a greeting card writer who falls for his coworker Summer. The film shows their relationship out of chronological order over 500 days. Tom believes in true love and thinks Summer is "the one" despite her warning him she doesn't want anything serious.

They have an on-again off-again romance with Tom hoping it will work out and Summer just going along for fun. In the end, Tom is heartbroken but realizes his expectations for their relationship were misguided, while Summer moves on quickly not believing in love.

DPM Top Picks

1. Clueless - One of the definitive teen comedies of the 90s, Clueless remains endlessly quotable while showcasing Alicia Silverstone's charming performance as the bubbly Cher.
2. 10 Things I Hate About You - This smart modernization of The Taming of the Shrew features a star-making turn from Julia Stiles and Heath Ledger as the mismatched couple.
3. Notting Hill - Few can resist the quirky British charm offensive of Julia Roberts and Hugh Grant in this warm romantic comedy hit.

Final Verdict

The 90s and 2000s offered an abundance of chick flicks spanning sweet first romances, witty satires, empowering stories, and tearjerking romances. Many have become beloved classics. These nostalgic films bottle the eras' entertainment trends and fashions while keeping the characters and stories timeless.

From Clueless to Notting Hill to A Walk to Remember, these chick flicks remind us how romantic comedies can make us laugh, swoon, reflect, and connect. Revisiting them recaptures the joy of an enchanting escape with endearing characters. These are comforting, inspiring films to experience any time you need some uplifting romance.

FAQs

Q: What makes a movie a chick flick?

Chick flicks are films marketed towards women featuring female-centered stories about love, romance, and relationships. Common chick flick tropes include meet-cutes, unrequited love, love triangles, makeovers, and happy endings.

Q: What movies represented the 90s?

Iconic 90s movies include Clueless, Titanic, Jurassic Park, Forrest Gump, Pulp Fiction, The Matrix, Goodfellas, Silence of the Lambs, Saving Private Ryan, Toy Story, Fight Club, and many more.

Q: Which chick flicks from the 90s and 2000s had strong female leads?

Chick flicks with strong female leads from the 90s-2000s include Clueless, Legally Blonde, 10 Things I Hate About You, Mean Girls, Miss Congeniality, Bring It On, Never Been Kissed, My Big Fat Greek Wedding, Ever After, etc.

Q: What are some must-watch chick flicks for a girls' night in from the 90s and 2000s?

Great chick flicks for a girls' night from the 90s-2000s include Clueless, Mean Girls, Bridesmaids, Legally Blonde, 13 Going on 30, Pitch Perfect, Sisterhood of the Traveling Pants, The Devil Wears Prada, How to Lose a Guy in 10 Days, Pretty Woman, etc.

Q: What was the highest grossing chick flick of the 1990s?

The highest grossing chick flick of the 1990s was Pretty Woman starring Julia Roberts and Richard Gere, which grossed over $463 million worldwide in 1990.