Top 10 Underrated ‘90s Hollywood Rom-Coms Films

The ‘90s in Hollywood was the golden age for romantic comedies. All of us hopeless romantics need to thank them for providing us with a lifetime of unrealistic expectations on romance and love. But also for giving us comfort and hope in gloomy times. We all are well-versed and well-educated in the schools of When Harry Met Sally (1989) and Notting Hill (1999). Meg Ryan and Julia Roberts have owned our hearts and it was a time when everyone fell in love with Hugh Grant. The beautiful montage in Clueless (1995), showing Cher falling in love with Josh, made us want to fall in love so badly. And how many times has one practiced saying “You Complete Me”, from Jerry Maguire (1996) to one’s imaginary partner? 

We have all put Sleepless in Seattle (1993) and Pretty Woman (1990) at the top of our lists but what about their other siblings? They have somewhat been overshadowed by these classics but they are just as good, warming our hearts as much. You will be shocked to know how you have barely scratched the surface when it comes to ‘90s Hollywood rom-com. Down below we have curated a list of 90s most underrated Hollywood rom-com. I know you have the time, so why don’t we go through the list together:

Drive Me Crazy (1999)

In the universe of High School, the biggest thing is Prom and the greatest insult is not have a date to go in with. Nicole (Melissa Joan Hart) and Chase (Adrian Grenier) have grown up next to each other but acquire very different spots in the school. While Nicole is part of the popular, cool group, Chase is always creating trouble, trying to undercut their snobbery. If Nicole is the institution, Chase is anti-institution. However, after Nicole is dumped by her date days before prom, she and Chase decide to go to prom together to get back at him. Maybe secretly Chase also wants to know what it feels like to be popular for once? Nevertheless, it is a start of a beautiful friendship. 

Fun Fact: The film was originally titled Next to You but was changed after one of its soundtracks, ‘You Drive Me Crazy’ by Brittany Spears. 

Picture Perfect (1997)

Kate (Jennifer Aniston) has a very linear way of viewing success in her life. She thinks one simply has to tweak certain things to make life look perfect. Hence, if the guy she likes is into bad girls, she will be a bad girl. Or if her boss is skeptical to give her a promotion because she isn’t well-settled, she is ready to bring a made-up fiance, Nick (Jay Mohr). And her life does end up looking picture-perfect, but she is not happy. Partly because it was never part of her plan to fall in love. This film also raises some key feminist issues such as Kate not getting a promotion because she is not “married” or being looked down upon just because she is a woman who is ambitious and successful at her job. Jennifer Aniston was part of other very remarkable rom-coms like The Object of My Affection (1998) and She’s the One (1996).

Frankie and Johnny (1991)

This film also took its title from a very popular American song ‘Frankie and Johnny.’ Frankie (Michelle Pfeiffer) is an emotionally scarred waitress who was physically abused in her first marriage. She has no dating life and is alone most of the time. Johnny (Al Pacino) is a middle-aged man who has just been released from prison. He is looking for a job and becomes a chef in Apollo Cafe where Frankie works. The film is about two extremely lonely people who wish to have someone in life. However, while Johnny is very eager to do so, it is Frankie who cannot make herself trust another person again. The film is so much about her struggles to overcome her fear and nightmares and fall in love again.  Obviously in real life, no one would believe that Pfeiffer has no dating life. 

One Fine Day (1996)

Another Michelle Pfeiffer movie! And this time she is starring with none other than George Clooney. One Fine Day does not exactly begin at a fine moment. Two single parents Melani Parker (Pfeiffer) and Jack Taylor (Clooney) have a very bad morning as they are late to drop their kids for a field trip. Melani works on some big architectural projects and Jack is a columnist from New York Daily News. Through a series of events and the switch-up of cell phones, they are forced to take care of each other’s kids and phone calls. The day does turn out to be more than fine at the end. The title of this movie comes from yet another 1963 song ‘One Fine Day’ by The Chiffons. 

While You Were Sleeping (1995)

Two times Sandra Bullock has left the man on the altar – in the 2009 film The Proposal and in this one. While in the former she was cold, business-savvy book editor, here she is a lonely fare token collector named Lucy. Lucy has a crush on the commuter Peter (Peter Gallagher) who is a perfect man because he never got to open his mouth. Just kidding but literally, Lucy’s first “meet-cute” with him is her saving Peter as he has been mugged and thrown over the tracks. She saves him but he is apparently in a medical coma. She takes him home and everyone in his family is somehow convinced that she is Peter’s fiance. But then enters Peter’s younger brother, Jack (Bill Pullman) and he and Lucy slowly fall in love with each other. The plot is fairly predictable but there’s the fun. Its strength lies in its charm. Here, love is more sweet than passionate. 

Reality Bites (1994)

Who would have thought Winona Ryder and Ethan Hawke will look so great on-screen? Hawke’s next film Before Sunrise gives us no shock that he chose to do Reality Bites. The film captures the hopes and ambitions of the youth, which they see fading away as they grow old. It begins with four friends who have recently graduated from college. Troy (Hawke) is a coffee-house guitarist while Lelaina Pierce (Ryder) is a budding filmmaker. However, growing up is not that easy and soon these four friends realize that the glamour of dreams is not so shiny. But at least they have got each other. The line that breaks me is when Lelaina mourns over how “she was really going to be something by the age of 23” and Troy consoles her by saying that “the only thing you have to be by the age of 23 is yourself.” And oh…Ben Stiller is also in the movie. 

Miami Rhapsody (1995)

If you haven’t fallen in love with Srah Jessica Parker’s curls by now, what is up with you? Gwyn Marcus (Parker) is engaged to her boyfriend Matt (Gill Bellows) Even though she loves him, she is scared to marry him because of her own commitment issues. Well, can you blame her? Every marriage in Gwyn’s family falling apart – her father feels alone in his marriage, her sister is sleeping with someone else, and his brother is only fighting with his wife. This movie has a lot of trademarks of Woody Allen comedies and some scenes can feel straight out of Annie Hall. However, David Frankel’s, the director’s, take on Allen’s comedies is very entertaining and emotionally poignant. The film also has one of the best ending lines. 

The Truth About Cats and Dogs (1996)

The movie is one of those light-hearted and warm films that you cannot help but like. Abby (Janeane Garofalo) is a radio jockey who gives advice to pet owners. As she gives advice to one of the callers called Brian (Ben Chaplin), he is instantly attracted to her voice and intelligence. He asks her to go on a date with him but Abby, who is low on self-esteem, decides to send Noelle (Uma Thurman), her attractive friend and neighbor, who is tall and blonde. In short, the total opposite of Abby. The film generates a lot of comedy and actually reminded me of Sierra Burgess Is a Loser (2018) in terms of the plot. 

The Mirror has Two Faces (1996)

The film is actually a very realistic and delicate look at sex and love. It follows two professors at the Columbia University slowly falling in love. Rose (Barbara Streisand) teaches English Literature while Gregory Larkin (Jeff Bridges) is a maths professor. Rose, in her 40s, has a non-existent dating life and has, more or less, given up on the prospects of marriage. Despite being of similar age and working at a similar place, Rose and Gregory couldn’t be more apart in their worldview. The latter has given up sex, having convinced himself that it is the source of ruin in his past relationships. Rose, on the other hand, cannot conceive of a relationship without physical intimacy. This movie has a lot of dialogues and conversations and it is, I feel, quite challenging in its subject matter. 

Fun Fact: Barbara Streisand directed the film

It Could Happen To You (1994)

The film is about a New York City police officer, Charlie Lang (Nicolas Cage), who wins a lottery and splits it with a waitress named Yvonne Biasi (Bridget Fonda). The movie is based on a real-life incident. The story’s plot is a type of situation one can never wonder happening to oneself and maybe that contributes to the dreamy aspect of the film. Aside from the fact that Charlie is a very kind and generous man to the point that he might actually be an angel in disguise. But that’s the whole point of the film. That things you never dreamt of happening to you, can do. The romance in the film is more subdued. The title is lifted from a song called ‘Young at Heart’ which begins with the line “Fairy tales can come true.”

How many have you watched and how many are you planning to?