We all remember the movie Clueless. It starts with the stereotypical rich blonde teenager who is the most popular girl in school and her transformation as she grows up. This movie is still remembered years later because Cher transforms from someone who only cares about herself and those she deems worthy of becoming a woman who cares about her as she strives to be a better person.
It is, of course, a romantic comedy, and there are great movies that are like Clueless that will make you laugh and connect with the character as they become different from who they thought they were.
10 Things I Hate About You
Like Clueless, this is a story that centers around the popular clique, but it also shows you the other side. It also shows just how complex the decision to have sex is when you are a teenager and why you shouldn’t be doing it. Each movie portrays a teen that has made the decision and those who have decided to wait.
Made in 1999, and it quickly became popular as it depicted the lives of two sisters. One sister is a social butterfly, the other an outcast who marches to her own drum. Their father makes a rule that the younger daughter can’t date until the older one does, so she hatches a plot with a would-be suitor to find her sister a fake boyfriend.
Unfortunately, her older sister develops feelings for the pretend boyfriend in the process. Starring Health Ledger, Julia Stiles, and other teen stars at the time, the movie was directed by Gil Junger and grossed $53.5 million worldwide. Easily one of our favorite movies.
Legally Blonde
The main character of Clueless is Cher. She’s smarter than she knows, but the world assumes she’s stupid because she’s blonde. She also has trouble finding true love but has fantastic friends that stick by her side.
Like Cher, she finds out that she has a lot more to offer than fashion and shopping when Elle enters Harvard Law school and sets out on the path to becoming a lawyer after her boyfriend dumps her and she wants him back. Made in 2001, it was directed by Robert Luketic and took off like a rocket. The cast includes Reese Witherspoon and Luke Wilson, among many other famous talents.
Spinoffs were made, and a play appeared on Broadway not long after the release. The third installment of the movie is planned for 2022. It grossed over $140 million worldwide and was nominated for two Golden Globes. Definitely another favorite.
Pretty In Pink
This is one of our favorites, but it is a well-loved classic by others. One of the most prominent themes in Clueless is that Cher learns that there is more to high school than cliques, popularity, and trying to change people when you shouldn’t. That is how Clueless ties into Pretty In Pink.
Andie is a more impoverished student and gets bullied by the ‘richies’ until one of them, named Blaine, decides to ask her out. While he doesn’t mean to, he puts down her friends unthinkingly, like saying they could crawl under a rock, and leaves Andie feeling as if he’s embarrassed to be seen with her.
Blaine has a lot of growing up to do by the end of the movie, and despite everything, Andie refused to change who she was. Likewise, Cher learned that Tai didn’t need to change and that Cher should never have told her who to date. Made in 1986 and directed by Howard Deutch, it has a fantastic soundtrack and stars Andrew McCarthy and Molly Ringwald. Making over forty million worldwide, it remains a classic people love.
The Breakfast Club
Five students get stuck in detention with each other and learn more about themselves and each other than they ever thought possible. At a first look, you may wonder why this is on the list and how it is similar to Clueless, but it is. Each student has to find out who they genuinely are, and like Cher, they undergo a transformation.
They also become friends and accept each other for who they are, like Cher’s relationship with Tai and her boyfriend. Directed by John Hughes, this movie came out in 1985. The Breakfast Club stars Judd Nelson, Molly Ringwald, and Emilio Estevez, along with the raw talents of Ally Sheedy and Anthony Michael Hall.
While it cost a million to make on its open weekend, it made over $51 million, according to Wikepia.com. In 2016 it was also selected for preservation as a significant film.
Mean Girls
Imagine for a second that Cher didn’t make a complete transformation, Tai ended up being more popular than her and staying that way, and the group breaks up and finds new friends. Or imagine if Cher was an outcast and gained popularity over everyone. Now you have Mean Girls.
Like Clueless, it deals with cliques, teens being awful to each other, and the main character learning a big lesson on treating people the right way. Cady is a teen from Africa who moves to America to attend school for the first time. Upon meeting the most popular group in school, she infiltrates it, trying to discover their world, only to realize she is actually falling into the trap.
Made in 2004, it was directed by Mark Waters and starred Lindsay Lohan and Rachel McAdams. A sequel was made, and a musical now grace the stages of Broadway. Grossing over $128 million worldwide, this film is still a sleepover must-have.
Confessions Of A Shopaholic
Made in 2009 and directed by P.J. Hogan, the film stars Isla Fisher and Hugh Dancy. Isla plays Becky. She is a shopping addict and works as a journalist but gains a job for a magazine to save money. She does well but feels awful knowing that she’s in massive debt.
Clueless fans will appreciate that, like Cher, Becky has a huge shopping problem but finds her inner worth and sees herself for who she is and not what she wears. Making more than $100 million worldwide, the reviews are mixed and ultimately optimistic and have a good message.
Emma
In this movie, we see Emma, a woman who loved to interfere in people’s love lives while her own is severely lacking. Remember Cher trying to fix up her teachers while having no dating life whatsoever? Based on the novel by Jane Austen, it stars Gwyneth Paltrow, Toni Colette, and Alan Cumming.
It won an Academy Award for its fabulous music score and was directed by Douglass McGrath in 1996.
She’s All That
Do you remember when Cher gives Tai a makeover and tries to make her popular? Freddie Prinze Junior does that to Laney, played by Rachael Leigh Cook. Laney is an artist and doesn’t realize that Zack has made a bet that he can turn her into a prom queen.
Both of them learn life-changing lessons by the end of the movie, and they both bring out the best in each other like Cher attempts to do with her friends before realizing that they are just fabulous the way they are and don’t need to change at all. Made in 1999 and directed by Robert Iscove, it had mixed reviews and made over $100 million worldwide.
Bring It On
A movie that gained popularity when it came out in 2000 stars Kirsten Dunst and Gabrielle Union. Two rival Cheerleading squads are fighting to prove they are the best as one finds out that every cheer they have has been ripped off from the other. Like Clueless, this deals with the pain of going through high school and trying to do the right thing.
Another way Kirsten’s character is like Cher’s is as she struggles to do the right thing when no one else wants to and is happy to take the easy way out. Directed by Peyton Reed, five sequels have come out in response. Grossing over $90 million, it remains a fan favorite to this day for many.
Easy A
In Clueless, Cher struggles to determine whether or not she is ready to lose her virginity. Easy A has the same situation, and only it shows what happens when you lie about losing it. Olive is the main character and is played by Emma Stone.
She is a virgin and has no problem being one but lies to her friend and says she lost it. Soon after, she helps her friend escape bullying by pretending to sleep with him. Once word gets out, teens are paying Olive to say that she slept with them even though she didn’t.
Only Penn Bagley’s character knows the truth. By the end of the movie, Olive is ostracized but redeems herself. Like Cher, she felt as if she had hit rock bottom but learned to find and love herself by the end.
A bit more modern than the others on this list came out in 2010 and was directed by Will Gluck. Though the budget was $8 million, it grossed $75 million worldwide.
Uptown Girls
Clueless fans got to see Cher grow by the end of the film. She became less self-absorbed and began to show that she cared about those around her. Brittany Murphey’s character in this movie is much the same.
Brittany plays a spoiled party girl who loses all of her trust fund money and takes a job as a nanny. Throughout the movie, you see her take a genuine growth as she starts to care for her charge, which Dakota Fanning plays. In 2003, it was directed by Boaz Yakin; it has positive reviews and took in more than $11 million in its first weekend.
A Cinderella Story
Pretend for a second that instead of being a popular girl, the main character of Clueless was a popular guy. In A Cinderella Story, Austin, who Chad Michael Murray plays, has everything he could want, except an understanding father and true love. His girlfriend is mean, shallow, and rude. Sam, Hilary Duff, is poor and an outcast.
The two begin talking online, not realizing who the other is, and by the end of the movie, Sam finds her inner strength like Cher does, while Austin learns that there are more important things than popularity and being mean to others. Directed by Mark Rosman in 2004, it grossed $70 million worldwide against a $19 million budget. It also spawned many sequels.
The Princess Diaries
Directed by Garry Marshall, this is a film that came out in 2001 and portrayed Mia. Mia is a teen who finds out that she is a princess. Starring Anne Hathaway, and Julie Andrews, it’s the story of Mia making life-changing choices, going from being invisible to being thrust in the spotlight, and how she realizes that your real friends will always be there for you.
Like Cher, she feels her emotions strongly and doesn’t understand what to do when her life suddenly changes. She also experiences feeling like she’s drifting apart from her friends, which is another way she relates to the characters in Clueless. Not to mention she has a friend that is just as opinionated as Dionne.
With a budget of $26 million, it grossed more than $160 million worldwide.
Romy And Michelle’s High School Reunion
Coming out in 1997, it was directed by David Mirkin; it stars Lisa Kudrow and Mira Sorvino along with Alan Cumming. Like Cher and Dionne, Romy and Michelle have a strong bond of friendship that wavers at times but is faithful to the end. There is also the added element of unrequited love that is clear in both films, which adds to the drama and the story.
It made $7 million on its first weekend, and reviews swing between positive and negative. Although people loved the friendship that was prominent throughout the movie, it reminds us that our real friends will never abandon us.
Drive Me Crazy
In 1999 everyone was going crazy for this movie. Directed by John Schultz, it follows Melissa Joan Hart as Nicole and Adrian Grenier as Chase. Nicole is popular and wants the most desirable date for the centennial dance.
However, he rejects her, so she teams up with her neighbor Chase who has also been dumped. Turning Chase popular to be an acceptable date, they realize they are falling for each other as they grow. This movie is well-liked by Clueless fans because both girls (Nicole and Cher) learn that you shouldn’t change people and that you should love your friends and potential suitors for who they are, and that you should remain true to yourself.
Grossing $22 million worldwide, it did well against an $8.5 million budget. Because Britney Spears released her song of the same name, this movie remains something that people love to experience repeatedly.
If you are looking to have the most fantastic night with friends or loved ones, these movies are guaranteed to be a hit among the crowd. Suppose you are having a marathon. Start with Clueless and see for yourself the beautiful connections these movies have to each other. Each one has an important lesson hidden inside the comedy and the drama. Above all, however, each film encourages people to stay true to themselves and not follow the crowd and fall into things that change who they are.
