Top 5 Nostalgic Movies from the 90s/00s

These nostalgic movies from the 90s/00s remind us of high school drama, the comedic reflection of how we acted, cliques, and the strive for popularity. However, these particular films share valuable lessons that teach us that individuality is more significant than any of that. 


10 Things I Hate About You

10 Things I Hate About You is the superior movie of the century (not biased at all). This movie delves into feminism, high-school drama, and rebellion whilst keeping a comedic flow. The main character, Kat Stratford, embodies the feminist heroine that is a powerhouse. There is a lot to take from this strong-willed character as she goes against societal expectations and lives in a world of her own, indulging in her music and literature. The plot takes a hilarious turn with the addition of bad boy, Patrick Verona, much to Kat’s annoyance. There is no movie like 10 Things I Hate About You; it is by far one of the most unique rom-coms out there. The large cast displays various characters, each with their interesting individual personality and traits that bring their own personal humour to the table. 

10 Things I Hate About You

What can we take from this movie? Apart from the film’s memorable soundtrack and the humour that makes you want to play the film again after finishing, 10 Things I Hate About You focuses on feminist matters. Lead character, Kat, is seen as the anti-social pessimist throughout the film by the surrounding characters. Still, realistically, she is the most robust character of them all that goes against societies expectations and preaches what she believes in, not caring what people think—a feminist hero.

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13 Going on 30

The 2004 movie, 13 Going on 30, goes from the pop-centred colourful world of the 80s to the 00s. Lead Jenna Rink brings forth an inspiring role and teaches us to be careful of what we wish for. The movie begins with Jenna as an awkward teenager in the 80s who just wants to fit in with the most popular girl group in school. This movie displays how being “cool” is not the desirable reputation you think you want, it shows that there is much more to that. 


This romantic comedy shows the beauty of being yourself and loving who you are through Jenna Rink’s lesson. With her high school best friend, Matt, the film warms its viewers’ heart by their reunion. The separation between the two best friends furthers Jenna’s understanding that her wishes becoming a reality was not the dreamy fantasy she hoped for. The life she beckoned affected the relationships she realised that was most important to her. Going from 13 to 30 made her realise that everything she ever wanted was right there in front of her all along.


Confessions of a Teenage Drama Queen

Lindsay Lohan’s leading role of Lola represents the character of self-expression. With a new town, new best friend, and the love of her favourite band, Sidarthur, she lives in a dream world. This movie raises the challenges of being a teenager to the surface. With the collision of the most popular girl in school and Lola, who tells little white lies to build a reputation for herself, she runs into complications that take a flip for the better as she meets her favourite musician.


Confessions of a Teenage Drama Queen is a fun and enjoyable movie full of adventure in New York City. This movie without a doubt keeps your attention to see what will happen next and if things will work out for Lola and her best friend, Ella as they find themselves in a complicated situation. This movie is certainly dramatic and is full of music that lifts your spirits; it has a musical element that adds excitement and dramatics to the plot.



Mid-90s movie, Clueless is memorable for its fashion, music, and fun. Clueless certainly is carried strongly by its cast and characters. The main character, Cher, portrayed by Alicia Silverstone, definitely is an individual that strives for their own well-being. She is a strong female character that focuses on learning from non-fictional books to benefit her as much as she can. You could say Cher tries to go against society’s expectations, but does she do it as well as Kat Stratford in 10 Things I Hate About You? Cher certainly cares for her popularity, yet, she is a kinder role than your typical mean, popular girl character. 


With new girl Tai joining the school, Cher makes it her mission to get her to fit in as much as possible. While Cher does this with the best intentions, she does not realise that Tai is more comfortable being herself rather than pretending to be a girly-girl to fit in. The moment we see the connection between Tai and the adorable skater boy Travis, there is a moment of realisation that the popular crowd are not who Tai wants to hang out with.

Clueless 2


Mean Girls

Last but certainly not least, there’s Mean Girls. Mean Girls by far is one of the most iconic, unforgettable, and original films out there. Mostly loved for its hilarious jokes and sly comedic moments. In another successful movie led by Lindsay Lohan, her character, Cady Heron, steals the thunder from the most popular (and powerful) girl in school, Regina George. Cady’s character starts off small; she is the new girl who becomes friends with the awesome duo, Damien and Janice. Janice and Damien, who are unapologetically themselves, face the tension between Regina and her group, The Plastics. Janice encourages Cady to accept their offering of her into their group to get insider information, only it being a catalyst for Cady to turn into something exactly like them, but worse. It was only a reminder for Cady, in the end, that what she needed was right there in front of her.


Mean Girls is at the top of my list for nostalgic teen comedies, as it explores the hilarious drama of high school and illustrates in the end how unnecessary popularity and fighting really is.


We learn from these movies to be yourself and not try to be someone we’re not to fit in. These films represent individuals and allow them to be unapologetically themselves eventually. While they give us entertainment and a good laugh, the representation of individualism and what is most important to you is what really matters. In the words of Kat Stratford, “you don’t always have to be who they want you to be, you know?”

Alison Law
Alison Law

Alison is a college student and writer passionate about the environment, fashion, animals and coffee.

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