9) Jerry Maguire (1996) 

For anyone who loved the Top Gun Maverick movie released this year, Jerry Maguire is right up your alley. Starring Tom Cruise, the movie follows the life of Jerry Maguire, a cocky and powerful sports agent who recently experienced a monumental setback due to his inappropriate behavior. Maguire then promptly finds himself fired and left to build his own company with a former colleague of his, Dorothy Boyd. The two are a very odd pairing, the bachelor and the single mother, or so they thought. Battling success and the onset of a new romantic relationship, they must work together to make sure their star athlete clients don’t crash and burn in the next season. 

8) Titanic (1997) 

The movie Titanic left an impression so big upon the romantic genre in the 90’s that it is still well known amongst youth today. Titanic is also a universal reference to the Romeo and Juliet scenario filled with emotional twists and dramatic effects. It begins with a young man, Jack Dawson (Leonardo DeCaprio) when he wins a third class ticket onto the new ship The Titanic and meets a first class beauty queen Rose Dewitt Bukater (Kate Winslet). As a poor boy who hopes to make a career out of being an artist, Jack falls hard for Rose after preventing her from jumping overboard. But Rose was supposed to marry another man, Caledon Hockley to maintain her family’s wealth and supremacy. Now Rose must make the decision between the two paths, and men that her life has presented her. The only problem; there is always something dangerous hidden in the water. 

7) Pretty Woman (1990)

Falling on the more mature side, Pretty Woman starring Julia Roberts and Richard Gere brings a bit more sophistication to this list. Likewise it might not be the most family forward film, but it is one that many people remember for the comedic effect and charm Roberts brings to the character Vivian Ward. This movie is great for people looking for content of an “unlikely” pairing, wealthy lifestyles, grand business deals, and a true vintage feel. 

6) The Parent Trap (1998) 

This version of the classic story of Hallie Parker and Annie James stars Lindsey Lohan as both of the mischievous twins who try and reunite their divorced parents after years of separation. While Hallie lives in California, Annie lives in London, both completely unaware of the other’s existence. That is until they both find themselves rivals at the same summer camp. Of course the preteens decide the only solution is to switch places and give their parents the shock of a lifetime. This movie is a wonderful film to watch as a family and has some of the best examples of 90’s fashions, friendships and much more. 

5) My Girl (1991) 

This heartbreakingly good movie is essential to the theme of growing up in the 90’s. However, I also recommend bringing a box of tissues along the way. The tear jerking film follows 11 year old Vada Sultenfuss whose mother passed away after her birth leaving her with her single dad, and grandmother. Vada has always been an outsider thanks in part to her dad owning a funeral home. Also, Vada’s tomboy status didn’t lend herself to having many friends. Her only true friend was a boy named Thomas J. Sennett. Vada and Thomas are normally inseparable, but things over the summer start to change and Vada eventually develops a big crush on her English teacher while Thomas is left to wonder whether she could ever feel that way about him. That is until one day when a heartbreaking moment changes everything. 

4) She’s All That (1999) 

She’s All That is the quintessential teen rom-com that would later give inspiration for The Cinderella Story and many other 2000s movie icons. The main character, Zach Siler, was one of the most popular boys at school until his hot shot girlfriend dumped him for a television star. Desperate to save his reputation Zach makes a bet he can turn any girl into a prom queen in just six weeks. Little does he know the nerd his friends picked, Laney Boggs is tougher to win over than he thought and just as he thinks he won the bet, his lies leave him dumbfounded over his true feelings for Laney. Taking place in a high school during the late 90’s and including a brief prom scene, the movie has excellent costuming, props, and locations to show off the best California during this decade. 

3) Clueless (1995) 

Ugh! As if high school in Beverly Hills during the 90’s couldn’t get more aesthetic, Cher Horowitz (Alicia Silverstone) has the entire place wrapped around her perfectly manicured finger. From boys, to designers, and of course her best friend Dionne everyone wants to be in her inner circle. But this coming of age movie takes a turn when Cher tries to give the new student Tai a makeover. Much to Cher’s astonishment, Tai quickly takes over her top spot in the high school hierarchy leaving her to realize just how wrong she really was. She came to this point of course with the help of her ex-stepbrother Josh who was never very keen on trends and social games but along the way he might have just been the one to win her heart. This movie is funny, lighthearted, and plays heavily into the ditzy blonde stereotype the 90’s is best known for. 

2) Drive Me Crazy (1999) 

And just like that we are down to the final two. Drive Me Crazy is similar to She’s All That, but this time both of the film’s main characters are in it to win it. Nicole and Chase are next door neighbors who couldn’t be more different. One a vying prom queen and the other an indie art boy they never before had a reason to speak to each other. But after both of them are left heartbroken after being dumped, the two form a plan to make both their ex’s jealous. As time goes by their fake dating seems to be working. When their friends start to see a change in them, the two start to question whether they even have to fake liking each other at all. 

1) 10 Things I Hate About You (1999)  

Of all the rom coms from the 90’s this one takes the cake. Julia Stiles and Heath Ledger do a phenomenal job at bringing their witty, stubborn, and abrasive characters to life. Additionally, 10 Things I Hate About You is comedic and feminist gold as it is one of the decade’s first films to feature a strong female lead with a somewhat realistic slow burn. It centers around Kat, a pretty and smart girl with a powerful feminist mind of her own who naturally scares off many of her fellow peers. However, Bianca, the bubbly younger sister of Kat has a rule from their dad saying she can only go on a date once Kat does as well. Hopeful, with the new arrival of charming boy Patrick being her perfect opportunity, Bianca tries to set the two up with a dare. But will Patrick’s charm be enough to win over Kat? Or will Bianca be out of luck again?