Did Emma, Clueless finds hyper-privileged yet good-intentioned teen Cher Horowitz playing matchmaker and makeover artist to her friends and teachers, only to realize the person she needs to work on is herself.
Everyone may have been social-distancing on Clueless' proper anniversary, July 19, and totally buggin' about it. So, here are 10 fun and frothy movies to escape in if you miss Cher and the gang.
Updated on September 30, 2020, by Richard Keller: Clueless was part of a genre that changed over the decades. Where coming-of-age movies of the 1980s profiled the gross and the sensual, ones made in the 1990s were more gentile. Such is the case with the movies on this list. Here are a few more for viewers to enjoy.
Never Been Kissed (1999)
This teen movie is not really a teen movie. It stars Drew Barrymore as 20-something journalist Josie Geller. She goes undercover at a high school for investigative research. In doing so, she undergoes a transformation.
Never Been Kissed is a coming-of-age story that happens later in life. Never popular at her own high school, Josie becomes the "It" girl in her undercover role. To the point that the coolest guy in the school asks her to the dance. Little does he know that Josie has her eyes on one of her teachers.
Pretty in Pink (1986)
One of the quintessential John Hughes movies of the 1980s was Pretty in Pink. Like Clueless, it's about high school love and social cliques. This time around, the main character isn't involved in either of them.
Molly Ringwald stars as Andie. She and her best friend Duckie, played by Jon Cryer, are constantly bullied by the "rich" cliques. However, one of their , Blaine (Andrew McCarthy), decides to ask her out and falls in love with her. Though there's a good deal of tension in Pretty in Pink, everything turns out okay in the end.
Easy A (2010)
Like Clueless, this teen movie from the 21st century takes its theme from another literary classic -- The Scarlet Letter. Emma Stone plays Olive, a 17-year-old who lies to her best friend to avoid going camping. The fib starts as simply a date. However, it eventually turns into something where she loses her innocence.
When the high school's church club hears this, they decide to make Olive their "project." In turn, she begins to dress more provocatively and even sews an "A" onto her clothes. Eventually, things get too big for Olive, so she needs to find a way to correct everything.
Heathers (1989)
Heathers takes the teen movie to another level. Over the years, it has become somewhat of a classic dark comedy. Winona Ryder plays Veronica, a high school student who belongs to an elite clique where she is the only one not named Heather. However, she has tired of their harshness and wants to go back to her nerdy roots.
Enter Christian Slater as J.D. -- a new student ready to shake things up. He certainly does when he and Veronica connect and start to eliminate the Heathers through dubious means. Though they are killed or injured, it seems viewers root more for Veronica and J.D. than the Heathers.
The Breakfast Club (1985)
The movie that established the Brat Pack as well as John Hughes' chops as a director of coming-of-age films. It is similar to Clueless in that all of the students in Saturday morning detention want to forcibly suggest changes to each other. However, what they need to do is repair themselves.
The 1985 film has an all-star cast that includes Ally Sheedy, Emilio Estevez, Anthony Michael Hall, Judd Nelson, and Molly Ringwald. Though they seem like teenage stereotypes at the beginning of The Breakfast Club -- Estevez as the jock, Sheedy as the emo, etc. -- they emerge from their cocoons as the movie draws to an end.
She's All That (1999)
Imagine a Clueless where Cher is a vapid teenage boy who objectifies women and the film's takeaway is that Tai is better off looking like a stereotypical hottie. That's what you get with She's All That. The premise: Freddie Prinze, Jr.'s Zack Siler takes a bet with an even jerkier friend (Paul Walker) that he can't make resident "ugly girl" nerd Laney (Rachael Leigh Cook) into a total smoke show. Her iconic, slow-mo walk down the stairs set to "Kiss Me" proves that he can.
Yes, She's All That is still a recommendation. Those looking to round-out their '90s teen movie viewing experience can't say the job is complete without checking this film off their list.
Love, Simon (2018)
For any viewer whose heart was all kinds of toasty warm after the sweet teen romances of Clueless, Love, Simon delivers the goods in that regard.
Simon is a well-off kid — not as rich as Cher, but he's got a pretty comfortable home life — who's popular and happy, except he's too afraid to come out as gay. When he romantically connects online to a mystery fellow male student at his school, Simon is on a quest to find him, but still wants to keep his identity a secret.
While it wasn't nearly as successful as Clueless, Love, Simon has the sweetness and levity of the classic teen films of the '80s and '90s.
Uptown Girls (2003)
Clueless fans' hearts were broken at Brittany Murphy's untimely ing. While the film was largely seen as a breakout for Alicia Silverstone, many pointed to Murphy as the true scene-stealer.
Uptown Girls is hardly the best film in the world, but it's packed with Murphy's charm. She plays a party girl who loses her trust fund money and is forced to take a job as a nanny. In other words, picture Cher with all her pampered privilege stripped away, and you have Uptown Girls.
Booksmart (2019)
While Tai had Cher to give her a makeover, the girls in Booksmart had to do it themselves.
Hyper-studious besties Molly (Beanie Feldstein) and Amy (Kaitlyn Dever) are shocked to discover they wasted their high school years hitting the books when their hard-partying classmates got into Ivy League schools as well. The girls decide to throw their rule book out the window for a night of wild fun.
Like Cher, Molly and Amy think they know it all, only to discover they've been clueless. Also, like the Clueless protagonist, the Booksmart girls win the audience over with their adorable personalities.
The Crush (1993)
It's one of Hollywood's greatest mysteries why Alicia Silverstone's career never really took off after Clueless. She's got the acting chops and comedic timing to be a leading lady of the silver screen.
But that's not to say Clueless was her only great role. Before the hit film, Silverstone starred in The Crush, an erotic thriller about a young teenage girl (Silverstone) who develops an unhealthy obsession with a handsome writer (Cary Elwes) who rents a room from the girl's parents.
Critics were not kind to The Crush, but it's the perfect movie to throw on on a rainy day. Plus, it'll be a huge treat for any Clueless fan to contrast Silverstone's very different performances.
