13 Best Movies like Clueless to Check Out

Are you clueless about what movies to watch if you liked Clueless? Well, worry not! Today, we will be showing you our list of the 13 best movies like Clueless. Get your popcorn ready because we will be in for a movie marathon!

We do not know about you, but we are excited about this list. Without further delay, let us get this show on the road!

Clueless (1995)

Clueless (1995)

Clueless is a comedy film that centers on the crazy but funny life of Cher Horowitz. It is a modern take on the old classic of Jane Austen – Emma.

The film is considered one of the best films of all time. That is why it comes as no surprise why it has garnered a following. A following big enough for a spin off sitcom and book series to be made to try and satisfy the hunger of its fans.

Now, that could still not be enough. No worries. You will likely find one or two films on this list for your fill.

The 13 Best Movies Like Clueless

You read that right. We have 13 movies on this list for you to check out. Without further ado, let us get to know our first film.

1. Legally Blonde (2001)

English 1h 36m IMDb

movies like Clueless Legally Blonde (2001)

Director: Robert Luketic

Stars: Reese Witherspoon, Luke Wilson, Selma Blair

Since we are talking about a big hit, let us start this list with a big hit! Let us talk about Legally Blonde first.

Legally Blonde is undoubtedly one of the most popular movies of all time. It came out in 2001, and even after more than two decades after its release, it still often makes its way into many must-watch lists.

This film centers on Elle Woods, her attempt to win her ex-lover, and her bizarre but much-earned triumph as a lawyer.

As we have said above, it is one of the most popular films. If you find that one Legally Blonde film is not enough, you need not worry. With its popularity, two other Legally Blonde films have been made. To top it off? There are talks that a third film is on the way!

2. The DUFF (2015)

English 1h 41m IMDb

movie like Clueless The DUFF (2015)

Director: Ari Sandel

Stars: Mae WhitmanBella ThorneRobbie Amell

The DUFF is a comedy film with a little bit of romance on the side. It centers on the life of Bianca Piper, her being the designated ugly fat friend, and her messy and quirky expedition to get rid of the title.

This film received positive reviews not only from the audience but the critics as well. It should not be surprising then that this movie was a hit when it came out. With a budget of approximately $8 million, it garnered around $43 million at the box office.

Here is a fun fact. Other than being great movies, another thing the DUFF shares with Clueless is that it also drew heavy inspiration from a novel.

3. The Kissing Booth (2018)

English 1h 45m IMDb

Clueless like movies The Kissing Booth (2018)

Director: Vince Marcello

Stars: Joey King, Jacob Elordi, Joel Courtney

Are you looking for something a little more recent? Let us go ahead and get to our next film then. Let us talk about The Kissing Booth.

This film is a comedy with a fair share of romance and a tiny bit of drama on the side. It focuses on Elle Evans, her friendship with Lee Flynn, and her romantic relationship with Noah Flynn.

This film is one of the best movies of 2018. You might have already heard of it, and maybe we did not even need to introduce it in the first place!

As proof of its success, it became the first installment of a trilogy. So, if you find yourself wanting more from this movie, you can go ahead and check out the second film that came out in 2020 and the third film that came out last 2021.

4. She’s All That (1999)

English 1h 35m IMDb

Clueless like movie She's All That (1999)

Director: Robert Iscove

Stars: Freddie Prinze Jr., Rachael Leigh Cook, Matthew Lillard

On the other hand, maybe you are looking for an oldie but goodie like Clueless. Well, our next movie might be for you. Let us talk about She’s All That next.

This movie is a comedy with a good amount of romance. It centers on Zack Siler, his fallout with Taylor Vaughan, and his eventual romance with Laney Boggs. The film also has a dash of drama, but we believe there would be more laughing than crying, especially when you see the ending of this film.

There is no doubt that this movie is one of the best movies. It was No. 1 in its first week, remained in the top 10 for sixteen weeks, and continues to make rounds today. If you want something that will not disappoint, this might be the movie to add to your watchlist!

5. Confessions of a Shopaholic (2009)

English 1h 44m IMDb

movies similar to Clueless Confessions of a Shopaholic (2009)

Director: P.J. Hogan

Stars: Isla Fisher, Hugh Dancy, Krysten Ritter

Have you ever heard of the book by Sophie Kinsella, Confessions of a Shopaholic? Well, you might be happy to know that it has a movie!

If you have read the novel, you might already have a good understanding of the premise of this movie. However, there is no need to worry for those who have not read the book yet. In summary, this film is a comedy sprinkled with some romance here and there. This movie centers on Rebecca Bloomwood, her spending habits, her career, and her association with Luke Brandon.

This movie was not well-received by the critics, but it seemed to have been well-received by the audience. For one, it had a box office of around $108 million! For another, it received several recognitions and nominations.

6. A Cinderella Story (2004)

English 1h 35m IMDb

movie similar to Clueless A Cinderella Story (2004)

Director: Mark Rosman

Stars: Hilary Duff, Chad Michael Murray, Jennifer Coolidge

As you might have already guessed, our next film is a modern take on one of our favorite fairytales – Cinderella.

A Cinderella Story is a comedy film with its fair share of romance. The film centers on its Cinderella, Samantha Montgomery (Sam). Similar to the happenings in the beloved fairytale, Sam faces cruelty from her stepmom and sisters, gets her Cinderella moment at the party in her school, and, of course, her happily ever after in the end.

The movie received negative reviews from critics. However, it was well-received by the audience, having garnered a box office hit of $70 million.

If you want to have a movie date with the family, many of the movies on this list will do. However, this one might be the best one to consider!

7. Pretty in Pink (1986)

English 1h 37m IMDb

Clueless similar movies Pretty in Pink (1986)

Director: Howard Deutch

Stars: Molly Ringwald, Jon Cryer, Harry Dean Stanton

Over here, we have another oldie but goodie. Let us talk about Pretty in Pink next.

This film is a comedy sided by a good amount of romance. It is about Andie Walsh and her association with Philip F. Dale and Blane McDonough. Additionally, it gives the audience a good look at concepts like love, cliques, and social standings at that time.

With its screenplay, the inclusion of some of the brat pack members, and the overall performance of the cast, it should not be surprising that it was able to be a hit. With a budget of around $9 million, it garnered approximately $40 million. However, that is not the only proof of its success. This film was also able to rack up a following.

Here is a fun fact. While certain films came about from a book, this movie produced a book instead!

8. Never Been Kissed (1999)

English 1h 47m IMDb

Clueless similar movie Never Been Kissed (1999)

Director: Raja Gosnell

Stars: Drew Barrymore, David Arquette, Michael Vartan

Over here, we have one of the funniest and most romantic films of all time – Never Been Kissed.

This film centers on Josie Geller and her crazy but humorous assignment. An assignment that ultimately led her to be comfortable in her own skin, see what truly matters, and find romance.

This movie had mixed reviews from critics. However, it has been well-received by the audience. Like many of the other films on this list, this one has racked up a following over the years. A fact that should not be surprising given the performance Drew Barrymore gave along with the whole gang.

9. 10 Things I Hate About You (1999)

English 1h 47m IMDb

best movies like Clueless 10 Things I Hate About You (1999)

Director: Raja Gosnell

Stars: Drew Barrymore, David Arquette, Michael Vartan

Next, let us talk about 10 Things I Hate About You. If you are a fan of old but gold romantic comedies, you might have probably heard of this one already.

This movie centers on Katarina Stratford and Patrick Verona, played by Julia Stiles and Heath Ledger. It is a modern take on The Taming of the Shrew, so if you have read the comedy, you will probably see its semblance with the film once you get to this classic.

This film was well-received by the critics and audience alike. It should not be surprising then to know this film has garnered tons of praise and recognition. If you want to start movie night on a good note, this film is one you want to consider.

10. Emma (1996)

English 2h IMDb

best movie like Clueless Emma (1996)

Director: Douglas McGrath

Stars: Gwyneth Paltrow, James Cosmo, Greta Scacchi

As we have said above, Clueless is a modern take on a novel by Jane Austen. If you want something a little closer to the books, you might want to check out our next film. Let us talk about Emma.

This movie centers on Emma Woodhouse and her matchmaking adventures. This film takes place in 19-century England, staying truer to the setting of the book. If you are on the lookout for a movie just like Clueless, this one is undoubtedly one to consider. After all, the two took inspiration from the same novel.

This film was well-received, not only by the critics but the audience as well. It even racked up nominations and awards!

11. Emma (2020)

English (United Kingdom) 2h 4m IMDb

new movies like Clueless Emma (2020)

Director: Autumn de Wilde

Stars: Anya Taylor-Joy, Johnny Flynn, Mia Goth

You read that right! We have another film entitled Emma. As you might have already guessed, this one also took inspiration from the book of Jane Austen.

Its story is pretty similar to the 1996 Emma. We still have Emma Woodhouse and all her shenanigans. However, we have a new cast with the lovely Anya Taylor-Joy playing Emma.

If you have room for two, you might want to add both versions. However, if you have to choose one, you might want to pick this version if you are particular with the cinematography. Both tell the same story, but they present it in different ways. It is more of a matter of preference if you have to pick between the two.

12. Easy A (2010)

English 1h 32m IMDb

new movie like Clueless Easy A (2010)

Director: Will Gluck

Stars: Emma Stone, Amanda Bynes, Penn Badgley

Over here, we have Easy A

Easy A is a comedy film served with a dash of romance. The film centers on the life of Olive Penderghast, who was played by the lovely Emma Stone.

Like Clueless, this film is a modern take on a literary work. Namely, The Scarlet Letter. If you have ever read the literature, you will undoubtedly find hard-to-miss similarities, which we believe you will find amusing.

With its screenplay, cast, along with everyone’s performance (with special mention for Stone), it should not be a surprise why this movie was a box office hit and continues to make rounds more than a decade after its release.

13. Mean Girls (2004)

English 1h 37m IMDb

list of Clueless movies in order Mean Girls (2004)

Director: Mark Waters

Stars: Lindsay Lohan, Jonathan Bennett, Rachel McAdams

Whether you have seen the film or not, you would likely agree that Mean Girls is one of the most talked-about films of all time. You have probably seen or heard a Mean Girls reference at least once in your life, whether you are aware of it or not. Well, maybe it is time to give it a shot.

This film is about Cady Heron as she navigates through her life at North Shore High School. As you might have already heard, you will meet many interesting characters in this film, like the infamous Regina George.

If you are down for something funny and light, Mean Girls is undoubtedly something you would want to consider.

Final Words

Today, we showed you our list of the 13 best movies like Clueless. As you have seen, many movies can match up to this classic. Some of the crowd favorites are on this list, like Legally Blonde and Mean Girls.

We also have many oldies but goodies like Lady in Pink and 10 Things I Hate About You. Of course, we also have some newer ones like Easy A and The Kissing Booth. Whatever you are in the mood for, we hope this list was able to help you fill your watchlist.

If you still need more movies for your movie marathon, you might want to check out our other lists!

Movie like Clueless to Check Out

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