How Well Do You Remember These 90's Rom-Coms?

Kennita Leon

Image: Miramax

About This Quiz

Romantic comedies offer viewers a two-in-one deal that not many other genres can. On the comedy side, we get to laugh and cry and on the romance side, we get to really cry. So, if you're a fan of doing both of these things, sometimes at the same time, then we've got an amazing quiz for you today. We're going to test your knowledge of some of the best romantic comedies in existence, but from a particular decade, the 1990s.

The '90s was such a fun decade, especially for movies, so it's no wonder why we want to bring them back and zoom in on one of the most successful genres. From "Clueless" to "The Wedding Singer" and "Pretty Woman" to "How Stella Got Her Groove Back," we had tons of options from which to choose if we wanted to be entertained. And we did. And we were.

So prove to us that you remember some of the movies that brought you joy, sadness and even love in the '90s and now if you like re-watching them. Show us that you remember the best romantic comedies of the '90s in this quiz. 

Who can ever forget Cher Horowitz? But what movie was she in?

Cher is a wealthy, spoiled teenager who acts as a matchmaker for her single friends while falling in love with her ex-stepbrother, Josh. She uses her wealth and charm to win her way through high school and has a fit when one of her minions, Tai, becomes more popular than her.

A crooner falls for someone else's bride in this movie. What is its name?

Adam Sandler stars as Robbie Hart, a broken-hearted wedding singer who falls in love with a waitress (actress Drew Barrymore) who is engaged to be married. This 1998 romantic comedy was a box office success, grossing more than $120 million worldwide against its $18 million budget.

Which 90's rom-com is this?

Julia Roberts stars as Vivian Ward, a prostitute hired by Edward Lewis (actor Richard Gere), to accompany him to social and business functions. As time progresses, the two become attracted to each other and learn to manage their unconventional relationship.

Six weeks to make a girl popular. Challenge accepted. In which of these movies did this happen?

Zack Siler is a high school jock recently dumped by his cheerleader girlfriend, Taylor, for Brock, the actor. The humiliated Zack takes up a challenge set by his friend Dean and attempts to transform the geeky Laney Boggs into prom queen material within six weeks.

In which movie did two rivals fall for each over internet correspondences?

Two business rivals, Kathleen Kelly and Joe Fox, unknowingly begin an anonymous online romance with each other. When Joe comes to realize Kathleen's true identity, he makes it his duty to win her over in real life. Meg Ryan and Tom Hanks assume the lead roles in this film.

Do you think you can identify this romantic comedy?

Two unaccomplished best friends, Romy and Michele, are wary of their upcoming 10-year high school reunion. They decide to create fake stories of elaborate and successful lives in order to impress their former classmates.

Would you ever date a girl for money? Well it happened in this movie. What was it called?

Bianca Stratford, a preppy social butterfly, comes up with a plan to get her cynical older sister, Kat, dating after her dad tells her she can't go out on a date with her crush, Joey Donner, until her sister has a date of her own. Larisa Oleynik stars as Bianca and Julia Stiles as Kat.

Which semi old-school movie is this?

The romantic affair between a widow, Sam Baldwin, and an engaged woman, Annie Reed, are made possible by the coaxing and interference of Sam's 8-year-old son Jonah, to find his dad a partner. Tom Hanks and Meg Ryan once again tap into their on-screen chemistry to bring forth this successful film.

A man goes through a lot of trouble and people to get a date from his high school crush. In what movie did this happen?

When Ted hires a private investigator, Pat Healy, to track down Mary, his high school crush, he hopes they can enjoy their long overdue date. Turns out just about everyone is in love with Mary and Ted must overcome the web of lies and his deceptive P.I. to win Mary's heart once and for all.

A woman goes undercover as a high school student and falls for a teacher. What's the name of this favorite?

A young copywriter poses as a high school student at her former school in order to conduct research for her work at the Chicago Sun-Times. She may be anticipating the students but what will she do when she realizes she has fallen in love with her handsome English teacher?

Can you tell us the name of this '90s movie?

Charles is an amiable bachelor who happens to attend several weddings and a funeral within a short space of time. He becomes infatuated with a woman named Carrie, with whom he has crossed paths at all of these gatherings, and becomes convinced they are meant to be.

Winning the lottery and splitting it in half? In what movie did this happen?

Charlie, an honest NYC police officer, remains true to his word and shares half his lottery winnings with waitress Yvonne Bias, much to the chagrin of his selfish wife, Muriel. As Charlie's friendship with Yvonne deepens, they must overcome the wicked schemes of their greedy spouses.

Falling for someone who isn't even attracted to your gender could be hard. In which movie did a man struggle through this?

Holden is a comic book artist who, much to his disappointment, falls in love with another artist, Alyssa, then finds out she's a lesbian. This film follows his relationship with his new love interest and his efforts to repair his friendship with his estranged best friend and business partner, Banky, who became threatened by Alyssa.

Of the options, which one seems like the name of this movie?

A sexually frustrated group of teenage boys make a deal to lose their virginity by prom. The nerdy and somewhat socially awkward friends learn lessons about dating, sex and the craziness of high school life.

An epiphany changed this sports agent for the better. Who was he?

After having an epiphany that changes his mindset, sports agent Jerry Maguire decides to make an honest living as a businessman and launch his own agency. His former employer remains disgruntled and conniving, so it's up to Jerry and his former secretary, Dorothy, to prove them wrong while exploring their new relationship.

Which movie do you think this is?

An overprotective father finds himself devastated when his eldest daughter returns from college engaged to be married. Now overwhelmed with finances and wedding plans, he must also sort through his emotional turmoil as he struggles to let her grow up.

A famous actress and a bookkeeper? In which movie did they try to make it work?

William Thacker is a bookstore owner who is delighted when Anna Scott, a world renown actress, enters his store to make a purchase. Later on, they begin to date after they cross paths, once again, and must juggle her fame and his friends around their new relationship.

It all goes wrong for one member of the wedding party, but in which movie?

All aspects of Harper Stewart's life seem to intertwine when he becomes the best man at his best friend's (Lance) wedding: his soon to be released autobiography dishes dirt on Lance's fiancé, he meets a former lover hell-bent on reconciliation while his current girlfriend, Robin, wants to get married too!

Can you tell us what this classic rom-com is called?

Alex Whitman, an American architect, has a one night stand with a beautiful Mexican-American photographer, Isabel Fuentes. When she returns months later with news of her pregnancy, the two decide to get married and soon learn about their different lives, careers and upbringing.

A woman who isn't allowed to act finds a way into this movie.

Shakespeare, a young playwright, falls in love and draws inspiration for his new play from Viola de Lesseps, the daughter of a rich businessman who disguises herself as a man to win a role in his play. This 1998 film is inspired by the actual work of William Shakespeare and other important figures in history.

Do us a favor and match this movie to its name.

Lelaina, a production assistant and a young filmmaker, documents her life and that of her close-knit group of friends. Vickie is a promiscuous sales associate, Sammy struggles with his homosexuality and, in between Troy's several jobs, he and Lelaina deny their romantic feelings for each other.

Two rivals fall in love through all their bickering in this film. What was its name?

Two opposing journalists, frequently at loggerheads with each other, are soon stars of their own "He Said She Said" program when their producer thinks their bickering will be great material for television. Lorie, the hopeless romantic, soon falls for sex-crazed Dan.

Two men fight for the love of a country star in this movie. Do you know its name?

Miranda Presley is an aspiring country music star who meets two potential suitors: James Wright and Kyle Davidson. She also befriends another artist, Linda Lue Linden, and together the four of them struggle to become accomplished artists while the two men both hope to win her affections.

What was the name of the romantic comedy shown in this screenshot?

This scene of this film is that of a graduation party of high school seniors. The cheerleaders, jocks, nerds and everyone in between gather at this house party-each with their own agenda in mind- revenge, sex and finding love.

A hot, but older woman falls in love with a young man on a tropical island. In which of these movies did this take place?

Stella, a single mother and a stockbroker, takes an exclusive vacation to Jamaica with her childhood friend, Delilah. While enjoying the sights of Jamaica, she must also find balance between motherhood, her career and her budding romance with a much younger man.

Can you tell us the name of this movie?

Ike Graham is a journalist who has branded Maggie Carpenter as a "Runaway Bride" after she ditches all her fiancés at the altar. When Graham travels to meet Maggie to get the real story, they fall in love. Will the love be strong enough to keep Maggie in position on her wedding day?

Pretending to be someone's wife while he's in a coma while falling for his brother must have been quite the story. Which movie told it?

Lucky Moderatz, a train station worker, saves the life of her crush, Peter Callaghan, after he is robbed and left in a coma. When the family mistakes her for his fiancé, the lonely Lucky follows with the pretense while falling in love with his brother, Jack.

An unlucky comedian finds love again in which of these movies?

Mike Peter is a comedian with a dull career and broken-hearted after his long-time girlfriend dumps him. As his guy friends try to get him back on track in the dating world, his neediness scares off potential suitors, except for one: the lovely Lorraine he meets outside a club.

What movie do you think this is?

Julianna Porter is the best friend of Michael O'Neals, her childhood buddy who is engaged to a 20-year-old beauty. Upon realizing that she is in love with him, the desperate maid of honor tries to thwart the wedding and gain Michael's affection.

A politician's daughter found herself and love in this movie. What was its name?

Muriel, the sheltered daughter of a politician, relocates out of her small town in order to find her true love and her independence. She changes her name and moves to Sydney with her friend Rhonda Epinstalk, and together they learn to maneuver life's challenges.

The leader of the free world single? Which movie tells the tale of him finding love again?

Andrew Shepherd, a widowed President of the United States, is captivated by Sydney Wade, an environmental lobbyist. The pair must find a way to deal with their mutual romantic interest and their passion for their careers that place them at loggerheads with each other.

A woman lies about her fiance in which of these movies?

Kate Mosley is an ambitious single woman who pretends to be engaged by showing off a photo of her "fiancé" so that she may be promoted at work. Her plan goes awry when her boss wants to meet her "fiancé," leaving Kate scrambling to locate the acquaintance with whom she faked a relationship.

Identify the '90's romantic comedy you see before you.

Two neighbors, Nicole and Chase, come up with a plan to pretend to be each other's partner to attract the attention of their love interests. Their bid to create jealously goes much better than they ever considered- when they genuinely begin to fall for each other.

Which of these movies tells the story of a weatherman stuck in a time loop?

Weatherman Phil Conners is horrified to discover that he is stuck in a time loop in Punxsutawney, Pennsylvania, on Groundhog Day. After much frustration, he learns a valuable life lesson and decides to make the best of his impossible situation.

Contemplating a career change? A weather man did in this movie. What was its name?

Successful Chicago weatherman, David Spritz, may be good at his job but he is very unhappy in his personal life. As he plans to makes major career moves, he must decide if it will be at the cost of his dwindling relationship with his family or if he can marry the two.

Can you tell us what this movie was called?

The romance between two artists- Nina, a photographer, and Darius, a writer- begins when they meet at Darius' poetry reading at the Sanctuary. Though their mutual interest is evident, Nina's past poses a threat to their potential courtship.

This is a classic Shakespeare tale. What is it called?

This comedy is mainly about four people - Hero and Claudia are a couple in love and soon to be married, while Benedick, a soldier, has a love-hate relationship with a woman named Beatrice. When Hero and Claudia experience problems, the once bickering couple cdeclare their love for each other and join forces to help their friends reconcile.

Tempting fate by asking your best friend to test your fiance's loyalty isn't a good idea. In which of these movies did it happen in?

Max, a sports broadcaster, is unsure of his upcoming marriage to Sam, an editor. He challenges his childhood best friend, Jay, to seduce Sam, and, if he is successful, it means she is not marriage material. However, as fate would have it, Sam and Jay spend time together and a romance ensues.

By what name did this romantic comedy go by?

​The life of Marcus Graham, a successful businessman and womanizer, quickly goes downhill when he meets and falls for Jacqueline, the company's new female boss. His work life becomes more complicated when he begins to date Angela, the assistant, while being toyed with by the dismissive Jacqueline.

Dancing without a partner just won't do. In which of these movies did a man train an inexperienced dancer so they could go for a championship?

The Pan-Pacific Grand Prix Dancing Championship is coming up and Scott Hastings, an accomplished Australian dancer, finds himself without a partner. Hesitantly, he begins to train Fran, an eager but inexperienced dancer, with only three weeks left before showtime.

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