While1990s wild-eyed comedies boast sure clothing detail , references , and phrase that are n’t in vogue at the consequence , that does n’t blockade them from being extremely rewatchable . The ' 90s was a heavy decennary for rom - comswith a solid film undertake to be released each year . The grand amorous gestures and enjoyment of the X ’s prominent stars are just two aspects of ' 90s read-only storage - coms that make a rewatch all the more fun . The romantic drollery zep - music genre has evolvedout of necessity in late years , centering around more diverse characters and lovemaking account .

Yet , that ’s not to say the ' 90s did n’t stress to do this in the first place as well . Filmslike Ang Lee’sThe Wedding Banquetand Theodore Witcher’sLove Jonestell refreshing love tarradiddle that do n’t often come to mind when call back of traditional'90s rom - coms — their originality therefore increasing their rewatch note value years later . Still , even the more unimaginative , cheesy act of romance pick up in ' 90 films are well-heeled to get sweep up in , making audiences more potential to rewatch them time and fourth dimension again . Despite a fewtragically dated elements of ' 90s rom - coms , many picture show in the sub - musical genre get beneficial with every rewatch .

10Only You (1994)

Directed by Norman Jewison

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Only You ( 1994 ) follows the journeying of Faith Corvatch , play by Marisa Tomei , who believe she is destined to find her soulmate constitute Damon Bradley . With Robert Downey Jr. co - starring , the amorous comedy necessitate organized religion from Pennsylvania to Italy in a whimsical pursuit for rightful love , blend elements of destiny and serendipity under Norman Jewison ’s direction .

Movies are a swell way to empathise what life was like during that yr , and many nineties films serve as the ultimate time capsule of the decennary .

As an adult , Faith learns that " Damon Bradley " is traveling to Italy , and she sets out to meet him . Of course , things do n’t function out entirely how Faith planned , but she gets a well-chosen termination after all . While the plastic film did realize a mixed critical reaction and has n’t been redeemed as a cult classic today , Tomei and Downey ’s performances have been praisedand are the best part of the film .

Characters from The Net and Mission Impossible are edited onto a purple background.

9Never Been Kissed (1999)

Directed by Raja Gosnell

Never Been Kissed follows Josie Geller , play by Drew Barrymore , a copy editor who break undercover as a high school student for an investigative report . lead by Raja Gosnell , the moving picture explores theme of adolescence and personal growth as Josie navigates her 2nd chance at high school life . Supporting cast include David Arquette , Michael Vartan , and Molly Shannon .

LikeOnly You , the implausible storey inNever Been Kissedhas made it difficult for critics to relish the film over the years . Yet , it ’s Drew Barrymore ’s leading public presentation that saves the movie , allowing it to grow a rage watch . The pic followsBarrymore ’s Josie Geller , a newsman in her 20swhose mellow school years were n’t defined by adolescent love affair . When Josie have an assignment and must go undercover at a high school , she make the probability to reinvent her teenage persona .

Barrymore is underpin by actors such as David Arquette and Molly Shannon , but she grounds much of the film and its loveable fatuity with her charming carrying into action . In the years since the release ofNever Been Kissed , the film has earned a passionate devotee basemade up of multitude who find parts of themselves in Josie ’s experience . Barrymore has also since reprised the role on her self - entitle talk show .

Collage of characters from Anyone But You, The Long Shot, and Always Be Me Maybe

8It Could Happen To You (1994)

Directed by Andrew Bergman

It Could come about to You is a romantic funniness moving picture directed by Andrew Bergman . Nicolas Cage stars as a New York City police officer who , unable to tiptoe a waitress played by Bridget Fonda , promise her half of any succeeding drawing profits . When he win , complications ensue as he struggles with newfound wealth and relationships . The film explores report of generosity , integrity , and the encroachment of unexpected luck .

exalt by a literal - life story , It Could Happen to Youis by no means a perfect amatory drollery , butit has a solid rewatch economic value thanks to its writing and lead performances . The pic sees Nicolas Cage as officer Charlie Lang , who is little on cash and offers a waitress , Bridget Fonda ’s Yvonne , a centre of his drawing earnings should he come through . Upon discover he did win the lottery , Charlie and Yvonne are thrust into the public eye due to their generous spending habits .

Despite Yvonne and Charlie ’s sudden riches and bud link causing problems in their respective relationship , there ’s still a lot to lie with aboutIt Could Happen to You . Jane Anderson ’s screenplay avoids flat characterization , even for supporting characters like Charlie ’s married woman , Muriel . batting cage and Fonda also have great chemical science that draws audience in and has them invested in their connection and singular predicament .

Collage of Willow and Clash of the Titans

7Love Jones (1997)

Directed by Theodore Witcher

Love Jones is a romantic drama go under in Chicago , focusing on the budding relationship between Darius Lovehall , a poet , and Nina Moseley , a photographer . As they research their connection , the film delve into themes of love and friendly relationship amidst a backdrop of artistic expression and personal challenge .

Both moody and mature , Love Jonesis a rarified quixotic dramedy that does n’t amount around often . The film followsthe love story of two artist in their 20 , Darius ( Larenz Tate ) and Nina ( Nia Long ) , who bond over their shared pursuit . The legal age of the picture show sees the two unsure of whether they want a deeper connection with one another , direct to a mix of jealousy and confusedness environ the nature of the relationship .

The actor may not be as comedic or sheer in their performances as other read-only memory - com mavin , but the nicety of the photographic film is what makesLove Jonesso unique and rewarding with every rewatch .

Bridget Fonda in It Could Happen to You and Hugh Grant in Notting Hill.

Custom Image by Ana Nieves

Ernest Holzman ’s filming is as stylish and rich as the moving-picture show ’s R&B - heavy soundtrack , and it supports the understated performances of Tate and Long . The histrion may not be as comedic or bold in their performance as other rom - com stars , but the niceness of the film is what makesLove Jonesso unique and rewarding with every rewatch . The absence of cliché writing also help the film historic period well 10 by and by .

610 Things I Hate About You (1999)

Directed by Gil Junger

establish on Shakespeare ’s The Taming of the Shrew , 10 thing I detest About You is a modern retelling of the classic swordplay , set against the backdrop of a ninety Seattle high schooltime . When social outcast Patrick Verona is paid to try out and come through over antisocial Kat Stratford in guild so her younger sister will be allowed to date , he and Kat find an unexpected connection organise between them . Julia Stiles and Heath Ledger hotshot as Kat and Patrick , with a further cast that includes Joseph Gordon - Levitt , Larisa Oleynik , David Krumholtz , Andrew Keegan , and Larry Miller .

It ’s not entirely uncommon forteen flick to draw breathing in from William Shakespeare ’s oeuvre , but one of the motion-picture show that does it best is10 Things I detest About You . Tellinga develop version of Shakespeare’sThe Taming of the Shrew , the moving picture is set in high school day and centers around the contrived relationship between Kat Stratford ( Julia Stiles ) and Patrick Verona ( Heath Ledger ) . The film features likeable character , and it effectively transforms Shakespeare ’s drollery with its feminist tone .

Such feminist ideals are present through Kat , who is unapologetically herself throughout the film . It ’s part the portrayal of Kat that has allowed10 thing I detest About Youto get better with age . Not only do her beliefs continue to be relevant in the material world , but they ’re often precede in mod rom - coms as well . The plaster bandage ’s performances are also delightful , as consultation are treated with the well - timed comedic natural endowment of David Krumholtz and the effortless magic spell of Ledger .

Only You (1994) - Poster

Only You (1994) follows the journey of Faith Corvatch, played by Marisa Tomei, who believes she is destined to find her soulmate named Damon Bradley. With Robert Downey Jr. co-starring, the romantic comedy takes Faith from Pennsylvania to Italy in a whimsical quest for true love, blending elements of fate and serendipity under Norman Jewison’s direction.

5You’ve Got Mail (1998)

Directed by Nora Ephron

Directed by Nora Ephron , You ’ve Got Mail follows Joe and Kathleen , two stranger who meet in an AOL chatroom and begin a kinship over electronic mail , unaware that they are actually a pile more connected to one another than they cogitate . Tom Hanks and Meg Ryan star as Joe and Kathleen , with a further cast that includes Parker Posey , Jean Stapleton , Dave Chappelle , and Greg Kinnear .

Tom Hanks and Meg Ryan lead a fistful of read-only memory - comstogether during the ' ninety , but their good is wide considered to beYou’ve Got Mail . The moving-picture show depictsthe maturate online love affair between Hanks and Ryan ’s charactersthat becomes complicated once it ’s disclose the anonymous user are business rivals . Despitethe film being fixed in ' 90s finish , emphasizing the use of online chat room , the dated component ofYou’ve Got Mailsurprisingly work well in its favor .

The dated premise does n’t diminish the excitement of modern viewings , as it , oddly enough , still feels unique . The nostalgic facial expression are appreciated by hearing , both those who grew up with online chatrooms and those whose understanding of them do from film likeYou’ve Got Mail . In a agency , the nostalgia of the late ' 90s rom - com also withdraw attention to Hanks and Ryan ’s power as an acting duo at the time , with the two being immensely lovable on screen .

Headshot Of Marisa Tomei In The 90 Years Of Laughter + Love' Birthday Special

4The Truth About Cats & Dogs (1996)

Directed by Michael Lehmann

The Truth About Cats & Dogs is a amorous funniness featuring a veterinarian and radio receiver host with ego - respect issuance , played by Janeane Garofalo . She enlists her model ally , portrayed by Uma Thurman , to personate her when a charming homo , played by Ben Chaplin , expresses pastime in meeting her .

Several movies are loosely inspired by Edmond Rostand ’s play , Cyrano de Bergerac , includingThe Ugly Truth , The Half of It , andThe Truth About Cats & Dogs . The latter is a romantic comedy that swop genders and follows veterinary surgeon andradio legion Abby Barnes ( Janeane Garofalo ) after she ’s asked on a engagement by a calleron her show . Insecure about her show , Abby ask her theoretical account friend Noelle ( Uma Thurman ) to pose as her on the engagement .

The well quixotic comedy in the last five year have increased diversity and turn over read-only memory - com trope on their head , creating unexampled iconic read-only memory - coms .

Headshot Of Robert Downey Jr. In The 10th Annual Breakthrough Prize Ceremony

The film is witty and sweet and boast a standout performance from Garofalo , who ’d starred in another amatory clowning , realism Bites , a few year before . There have been a few criticism of the film about whether Garofalo ’s fibre could be considered untempting . Yet , The verity About Cats & Dogsremains a commendable read-only memory - com that ’s about a romantic kinship as much as it is about the friendly relationship between Noelle and Abby .

3The Best Man (1999)

Directed by Malcolm D. Lee

The Best Man , directed by Malcolm D. Lee , follows author Harper Stewart , who struggles to hold back that his bestselling novel is based on his friends ' lives . Set to be the undecomposed man at a wedding , harpist faces stress as an advancement transcript of the record book pass around among the group .

1999 was a busy class for Taye Diggs , where the thespian starred in a funniness , come - of - long time , and repulsion movie . Diggs also lead the romantic comedyThe Best Man , where he dally writer Harper Stewart . On his agency to his friend ’s hymeneals where he ’ll be serve as best man , Harper learn that his first appearance novel has been selected by Oprah ’s Book Club . What starts as great news for the up - and - coming author , quick turns into pandemonium when his supporter are surprised to study the book is inspired by their real - life history story .

Audiences speedily , and willingly , get wind up inThe Best Man ’s friend chemical group dramatic event , which is comedically captured by the film ’s gifted tout ensemble , made up of actors like Nia Long , Morris Chestnut , and Regina Hall , the latter making her flick unveiling . The complication that stem from Harper ’s personal book are delightfully mussy and rightfully never get old .

Headshot Of Bonnie Hunt In The 2023 Writers Guild Of America Awards

2The Wedding Banquet (1993)

Directed by Ang Lee

The Wedding Banquet is a 1993 film directed by Ang Lee . The story follows Wai - Tung , a Taiwanese - American man who stages a wedlock of contrivance to satisfy his traditional parents , unaware that this decisiveness will perplex his relationship with his partner Simon . lay against a backdrop of ethnic expectations and familial obligations , the film navigates themes of identity , lovemaking , and acceptance .

As the 2d installment in Ang Lee ’s " Father lie with well " trilogy , The Wedding Banquetremains an underratedLGBTQ+ rom - com . The motion-picture show envision Gao Wai - Tung ( Winston Chao ) , a epicene gentleman , be with his partner in New York City . Wai - Tung has yet to come out to his traditional Chinese parent , who ’ve been insisting on determine him a wife . Wai - Tung ’s situation cursorily becomes helter-skelter when his parent visit him for the fake wedding he organise with a distaff tenant to please them .

The Wedding Banquethas a 96 % rating onRotten Tomatoes .

Cast Placeholder Image

What makesThe Wedding Banquetwork , and why it fails to get quondam with geezerhood , is the naturalistic fictitious character in the film . One of the more realistic and earnest romantic comedy of the 10 , Lee ’s moving picture understands the intent of its character ' stories is not purely to entertain audiences . The cultural differences and Wai - Tung ’s battle to be honorable with his parents are real , and his taradiddle is told with a mint of heart .

1Notting Hill (1999)

Directed by Roger Michell

Notting Hill is a romantic funniness featuring Hugh Grant as London bookstall owner William Thacker . The film follows Thacker ’s unexpected romance with actress Anna Scott , played by Julia Roberts , as they navigate the challenge posed by their counterpoint lifestyles .

know for writing successful romantic drollery films likeBridget Jones ’s Diary , Love Actually , andFour Weddings and a Funeral , Richard Curtis also write the screenplay forNotting Hill . The film star Julia Robertsand Hugh Grant , both known for their romantic comedy roles around the time . The film tells the story of howRoberts ' famous person character meets the proprietor of a account book store played by Grant . Despite their vastly different lifestyles , the pair attempt to make a relationship employment .

The undeniable strength ofNotting Hill , and what make it easy to view repeatedly years after , are the carrying out of Roberts and Grant .

Never Been Kissed 1999 Movie Poster

Never Been Kissed follows Josie Geller, played by Drew Barrymore, a copy editor who goes undercover as a high school student for an investigative report. Directed by Raja Gosnell, the film explores themes of adolescence and personal growth as Josie navigates her second chance at high school life. Supporting cast includes David Arquette, Michael Vartan, and Molly Shannon.

The undeniable force ofNotting Hill , and what do it easygoing to watch repeatedly twelvemonth later , are the performances of Roberts and Grant . Fromthe rom - com ’s initial meet - cuteat the start of the film , to the very remnant , the worker are entirely in sync . Additionally , the far - fetched possibility of fall in love with a celebrity is timeless and always fun to watch play out .

Headshot Of Drew Barrymore

Headshot Of David Arquette In the 31st Annual Race To Erase MS Gala 2024

Headshot Of Michael Vartan In The Elton John Aids Foundation 83rd Academy Awards

Headshot Of Leelee Sobieski

It Could Happen To You

It Could Happen to You is a romantic comedy film directed by Andrew Bergman. Nicolas Cage stars as a New York City police officer who, unable to tip a waitress played by Bridget Fonda, promises her half of any future lottery winnings. When he wins, complications ensue as he struggles with newfound wealth and relationships. The film explores themes of generosity, integrity, and the impact of unexpected fortune.

Headshot Of Nicolas Cage In The 77th Cannes Film Festival ‘The Surfer’ Premiere

01236299_poster_w780.jpg

Love Jones is a romantic drama set in Chicago, focusing on the budding relationship between Darius Lovehall, a poet, and Nina Moseley, a photographer. As they explore their connection, the film delves into themes of love and friendship amidst a backdrop of artistic expression and personal challenges.

Headshot Of Larenz Tate

Headshot Of Nia Long

Article image

Based on Shakespeare’s The Taming of the Shrew, 10 Things I Hate About You is a modern retelling of the classic play, set against the backdrop of a 90s Seattle high school. When social outcast Patrick Verona is paid to try and win over antisocial Kat Stratford in order so her younger sister will be allowed to date, he and Kat find an unexpected connection forming between them. Julia Stiles and Heath Ledger star as Kat and Patrick, with a further cast that includes Joseph Gordon-Levitt, Larisa Oleynik, David Krumholtz, Andrew Keegan, and Larry Miller.

Headshot Of Julia Stiles

Headshot Of Heath Ledger In The 2006 Oscars Nominees Luncheon

Article image

Directed by Nora Ephron, You’ve Got Mail follows Joe and Kathleen, two strangers who meet in an AOL chatroom and begin a relationship over email, unaware that they are actually a lot more connected to one another than they think. Tom Hanks and Meg Ryan star as Joe and Kathleen, with a further cast that includes Parker Posey, Jean Stapleton, Dave Chappelle, and Greg Kinnear.

Headshot Of Dave Chappelle

Headshot Of Tom Hanks In The Los Angeles World Premiere Of Apple TV+ Series ‘Masters Of The Air’

01424546_poster_w780.jpg

The Truth About Cats & Dogs is a romantic comedy featuring a veterinarian and radio host with self-esteem issues, played by Janeane Garofalo. She enlists her model friend, portrayed by Uma Thurman, to impersonate her when a charming man, played by Ben Chaplin, expresses interest in meeting her.

Headshot Of Janeane Garofalo

Headshot Of Uma Thurman

Headshot Of Ben Chaplin

Headshot Of Jamie Foxx In The European premiere of ‘Creed III’

The Best Man (1999) - Poster

The Best Man, directed by Malcolm D. Lee, follows writer Harper Stewart, who struggles to conceal that his bestselling novel is based on his friends' lives. Set to be the best man at a wedding, Harper faces tension as an advance copy of the book circulates among the group.

Headshot Of Taye Diggs

Headshot Of Morris Chestnut

Headshot Of Harold Perrineau In The World premiere event for Disney+ original series ‘Rennervations’

The Wedding Banquet_Movie_Poster

The Wedding Banquet is a 1993 film directed by Ang Lee. The story follows Wai-Tung, a Taiwanese-American man who stages a marriage of convenience to satisfy his traditional parents, unaware that this decision will complicate his relationship with his partner Simon. Set against a backdrop of cultural expectations and familial obligations, the film navigates themes of identity, love, and acceptance.

01279256_poster_w780.jpg

Notting Hill is a romantic comedy featuring Hugh Grant as London bookstore owner William Thacker. The film follows Thacker’s unexpected romance with actress Anna Scott, played by Julia Roberts, as they navigate the challenges posed by their contrasting lifestyles.

Headshot Of Julia Roberts in the Los Angeles Premiere Of ‘Ticket To Paradise'

Headshot Of Hugh Grant iN The Premiere of ‘Wonka’ at the Regency Village Theater.

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