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It’s hard to believe it’s been three decades since the absolute cultural phenomenon that is Clueless hit theatres. What began as a modernised spin on Jane Austen’s Emma morphed into a generational style bible, teen comedy staple, and pop culture powerhouse. Photo: Paramount
2/50It’s hard to believe it’s been three decades since the absolute cultural phenomenon that is Clueless hit theatres. What began as a modernised spin on Jane Austen’s Emma morphed into a generational style bible, teen comedy staple, and pop culture powerhouse. Photo: Paramount
Fast-forward to 2025, and the film still slays. I dare you to attend a Halloween party without spotting at least one Cher or Dionne. But what became of the most influential Beverly Hills kids of the 90s? Buckle up as we scroll through the surprisingly spicy, devastatingly touching, and occasionally ‘totally hagsville’ paths the Clueless cast has wandered over the past 30 years. Photo: Paramount
3/50Fast-forward to 2025, and the film still slays. I dare you to attend a Halloween party without spotting at least one Cher or Dionne. But what became of the most influential Beverly Hills kids of the 90s? Buckle up as we scroll through the surprisingly spicy, devastatingly touching, and occasionally ‘totally hagsville’ paths the Clueless cast has wandered over the past 30 years. Photo: Paramount
When Alicia Silverstone slipped into her Mary Janes and plaid blazer, she became an instant icon. At just 18, she infused Cher Horowitz with charm, warmth, and impeccable comedic timing. Photo: Paramount
4/50When Alicia Silverstone slipped into her Mary Janes and plaid blazer, she became an instant icon. At just 18, she infused Cher Horowitz with charm, warmth, and impeccable comedic timing. Photo: Paramount
Audiences fell for Cher’s good intentions, flawless wardrobe, and the kind of confidence that made being clueless feel aspirational. Off-screen, Alicia signed a massive film deal, with studios banking on her becoming the next big thing. And while the 90s didn’t stay kind to every teen star, Alicia carved out a path that was distinctly her own. Photo: Paramount
5/50Audiences fell for Cher’s good intentions, flawless wardrobe, and the kind of confidence that made being clueless feel aspirational. Off-screen, Alicia signed a massive film deal, with studios banking on her becoming the next big thing. And while the 90s didn’t stay kind to every teen star, Alicia carved out a path that was distinctly her own. Photo: Paramount
Fast forward to 2025, and Alicia is back in Cher’s shoes, this time also stepping in as executive producer. The upcoming Clueless reboot on Peacock promises to drop our favourite LA girl into a modern world brimming with social media drama, activism, and gender politics, all filtered through that same signature optimism. Now 48, Alicia has called the return “surreal”, a joyful full-circle moment that blends nostalgia with evolution. Fans are eager to see where she takes the character next. After all, “women are the real architects of society.” Photo: Getty
6/50Fast forward to 2025, and Alicia is back in Cher’s shoes, this time also stepping in as executive producer. The upcoming Clueless reboot on Peacock promises to drop our favourite LA girl into a modern world brimming with social media drama, activism, and gender politics, all filtered through that same signature optimism. Now 48, Alicia has called the return “surreal”, a joyful full-circle moment that blends nostalgia with evolution. Fans are eager to see where she takes the character next. After all, “women are the real architects of society.” Photo: Getty
Alicia’s recent acting choices have been refreshingly fearless. She’s embraced gritty, offbeat roles in indie films like Reptile and Y2K. In a particularly spicy move, she stars in a newly-released erotic drama titled Pretty Thing, which has already stirred plenty of buzz. Alicia Silverstone really said, “I have range,” because erotica is a long way from high school hallways and debate class. Photo: Yale Entertainment
7/50Alicia’s recent acting choices have been refreshingly fearless. She’s embraced gritty, offbeat roles in indie films like Reptile and Y2K. In a particularly spicy move, she stars in a newly-released erotic drama titled Pretty Thing, which has already stirred plenty of buzz. Alicia Silverstone really said, “I have range,” because erotica is a long way from high school hallways and debate class. Photo: Yale Entertainment
Outside of acting, Alicia has built a life that blends wellness, family, and activism. She’s a vocal advocate for animal rights and plant-based living, even publishing bestsellers like The Kind Diet. She’s also known for being a hands-on mum, sharing her unconventional but loving parenting journey with her son Bear. Cher would be so proud. Photo: Variety
8/50Outside of acting, Alicia has built a life that blends wellness, family, and activism. She’s a vocal advocate for animal rights and plant-based living, even publishing bestsellers like The Kind Diet. She’s also known for being a hands-on mum, sharing her unconventional but loving parenting journey with her son Bear. Cher would be so proud. Photo: Variety
While Cher was technically the ‘main character’, Dionne was never just a sidekick. The fierce, fashionable, clap-backing character was a force behind Clueless’ cultural dominance. Played with razor-sharp confidence by Stacey Dash, Dionne brought major attitude to every scene and stole plenty of them. Photo: Paramount
9/50While Cher was technically the ‘main character’, Dionne was never just a sidekick. The fierce, fashionable, clap-backing character was a force behind Clueless’ cultural dominance. Played with razor-sharp confidence by Stacey Dash, Dionne brought major attitude to every scene and stole plenty of them. Photo: Paramount
Her oversized hats, impeccable hair and make-up, and sassy Murray jabs made her truly iconic.
10/50Her oversized hats, impeccable hair and make-up, and sassy Murray jabs made her truly iconic. "I do not wear polyester hair, okay? Unlike some people I know like Shawana." At 28, Dash was a decade older than her character, but you’d never know it. If Cher was the heart of the movie, Dionne was the pulse. Photo: Paramount
After the film, Stacey Dash stayed in the game. She reprised her role in the Clueless TV series and landed supporting roles in romantic comedies and dramas. Her looks, talent, and screen presence kept her booked and busy well into the early 2000s. Photo: Paramount
11/50After the film, Stacey Dash stayed in the game. She reprised her role in the Clueless TV series and landed supporting roles in romantic comedies and dramas. Her looks, talent, and screen presence kept her booked and busy well into the early 2000s. Photo: Paramount
But as her acting slowed down, Dash made a move no Clueless fan had on their bingo card. She entered the world of political commentary and joined Fox News as a contributor. Her conservative views shocked many of her fans, sparking headlines and controversies that quickly eclipsed her acting. A quick search on TikTok reveals she’s the one castmate the younger generations can’t get behind. Stacy went from Clueless to cancelled. Photo: Fox News
12/50But as her acting slowed down, Dash made a move no Clueless fan had on their bingo card. She entered the world of political commentary and joined Fox News as a contributor. Her conservative views shocked many of her fans, sparking headlines and controversies that quickly eclipsed her acting. A quick search on TikTok reveals she’s the one castmate the younger generations can’t get behind. Stacy went from Clueless to cancelled. Photo: Fox News
In recent years, Stacey has stepped back from political firestorms and entered a more introspective era. She’s been open about past struggles with addiction and trauma, speaking at events and on podcasts about healing. In 2023, she released a memoir detailing the pressures of fame, faith, and self-discovery. These days, she seems more focused on self-growth and quiet reflection than the spotlight. Whether she returns to acting full-time remains uncertain, but her journey from Dionne to who she is now has been anything but predictable. Photo: Getty
13/50In recent years, Stacey has stepped back from political firestorms and entered a more introspective era. She’s been open about past struggles with addiction and trauma, speaking at events and on podcasts about healing. In 2023, she released a memoir detailing the pressures of fame, faith, and self-discovery. These days, she seems more focused on self-growth and quiet reflection than the spotlight. Whether she returns to acting full-time remains uncertain, but her journey from Dionne to who she is now has been anything but predictable. Photo: Getty
Paul Rudd’s character Josh was the original slow-burn heart-throb. Sarcastic, socially aware, and carrying just the right amount of nerdy charm. As Cher’s college-aged ex-stepbrother (go ahead, say that ten times fast), his storyline should have been … questionable. Photo: Paramount
14/50Paul Rudd’s character Josh was the original slow-burn heart-throb. Sarcastic, socially aware, and carrying just the right amount of nerdy charm. As Cher’s college-aged ex-stepbrother (go ahead, say that ten times fast), his storyline should have been … questionable. Photo: Paramount
But Paul Rudd is Paul Rudd, and somehow he made it warm, funny, and naturally wholesome. We were all rooting for Josh. He set the bar for an entire generation’s dating standards: smart, quietly attractive, funny, protective in a non-toxic way. Wait, does this guy even exist in real life? I may have just realised why I’m single. And I blame Josh. Photo: Paramount
15/50But Paul Rudd is Paul Rudd, and somehow he made it warm, funny, and naturally wholesome. We were all rooting for Josh. He set the bar for an entire generation’s dating standards: smart, quietly attractive, funny, protective in a non-toxic way. Wait, does this guy even exist in real life? I may have just realised why I’m single. And I blame Josh. Photo: Paramount
The role launched Rudd’s career, which has only become more unstoppable with time. Arguably the most successful of the Clueless cast, he’s now one of Hollywood’s most beloved faces. From Clueless to rom-com hits like Role Models and I Love You, Man, he proved he could lead a comedy without being a jerk. Then he shrank into a Marvel superhero and made Ant-Man a household name. Hands down, the funniest Avenger. Also, casually saved half the universe. No big deal. Photo: Disney
16/50The role launched Rudd’s career, which has only become more unstoppable with time. Arguably the most successful of the Clueless cast, he’s now one of Hollywood’s most beloved faces. From Clueless to rom-com hits like Role Models and I Love You, Man, he proved he could lead a comedy without being a jerk. Then he shrank into a Marvel superhero and made Ant-Man a household name. Hands down, the funniest Avenger. Also, casually saved half the universe. No big deal. Photo: Disney
Somewhere between saving humanity and making people laugh-cry, he also earned the unofficial title of ‘Nicest Man in Hollywood’. In 2021, People named him ‘Sexiest Man Alive’, and the internet promptly imploded. Not bad for a guy who started out doing homework on Cher’s couch. Photo: People Magazine
17/50Somewhere between saving humanity and making people laugh-cry, he also earned the unofficial title of ‘Nicest Man in Hollywood’. In 2021, People named him ‘Sexiest Man Alive’, and the internet promptly imploded. Not bad for a guy who started out doing homework on Cher’s couch. Photo: People Magazine
Off-screen, he co-founded a candy shop in New York to support local communities, attends cancer fundraisers, and always makes time for fans. He’s stayed married to the same woman for over two decades, raised two kids, and somehow dodged the usual celebrity scandals entirely. While he’s not officially part of the Clueless reboot (yet), fans are crossing everything for a surprise cameo. Let’s be so for real. What’s a Clueless update without a little Josh wisdom? If anyone can still play the same role 30 years later, it’s Paul Rudd. The man is clinically incapable of ageing. Photo: Deadline
18/50Off-screen, he co-founded a candy shop in New York to support local communities, attends cancer fundraisers, and always makes time for fans. He’s stayed married to the same woman for over two decades, raised two kids, and somehow dodged the usual celebrity scandals entirely. While he’s not officially part of the Clueless reboot (yet), fans are crossing everything for a surprise cameo. Let’s be so for real. What’s a Clueless update without a little Josh wisdom? If anyone can still play the same role 30 years later, it’s Paul Rudd. The man is clinically incapable of ageing. Photo: Deadline
Murray might’ve just been Dionne’s boyfriend, but he brought hilarious energy to every scene. Donald Faison turned what could’ve been a background role into a breakout one. Photo: Paramount
19/50Murray might’ve just been Dionne’s boyfriend, but he brought hilarious energy to every scene. Donald Faison turned what could’ve been a background role into a breakout one. Photo: Paramount
His freeway argument with Dionne remains one of the funniest, most iconic moments in movie history. Beneath the jokes, though, Faison gave Murray more depth than expected. He was loyal, emotional, and endearingly clueless about women. Photo: Paramount
20/50His freeway argument with Dionne remains one of the funniest, most iconic moments in movie history. Beneath the jokes, though, Faison gave Murray more depth than expected. He was loyal, emotional, and endearingly clueless about women. Photo: Paramount
After Clueless, Donald Faison found his true home on television. He landed the role of Dr Chris Turk on Scrubs, which ran for nine seasons and made him a household name. His chemistry with Zach Braff helped define the show’s emotional core and gave pop culture one of its all-time great TV bromances. Off set, he stayed booked, working steadily in everything from voice acting to guest sitcom roles. By the 2010s, he was as recognisable as ever, with a fanbase that spanned generations. Photo: abc
21/50After Clueless, Donald Faison found his true home on television. He landed the role of Dr Chris Turk on Scrubs, which ran for nine seasons and made him a household name. His chemistry with Zach Braff helped define the show’s emotional core and gave pop culture one of its all-time great TV bromances. Off set, he stayed booked, working steadily in everything from voice acting to guest sitcom roles. By the 2010s, he was as recognisable as ever, with a fanbase that spanned generations. Photo: abc
Now in his late 40s, he’s fathered what can only be described as a small classroom of children. Six kids, to be exact. Faison continues to act and has also carved out a strong presence as a host and podcast voice. He co-hosts Fake Doctors, Real Friends with Zach Braff, a behind-the-scenes dive into their Scrubs days that people clearly can’t get enough of. It’s me. I’m ‘people’. Photo: Fake Doctors, Real Friends
22/50Now in his late 40s, he’s fathered what can only be described as a small classroom of children. Six kids, to be exact. Faison continues to act and has also carved out a strong presence as a host and podcast voice. He co-hosts Fake Doctors, Real Friends with Zach Braff, a behind-the-scenes dive into their Scrubs days that people clearly can’t get enough of. It’s me. I’m ‘people’. Photo: Fake Doctors, Real Friends
Every teen comedy needs someone to roll their eyes and throw shade. Enter Amber Mariens. Played to perfection by Elisa Donovan, Amber was the overstyled, over-it snob who lived for drama. Donovan gave her just enough exaggeration to make her ridiculous, but still irresistibly fun to watch. Photo: Paramount
23/50Every teen comedy needs someone to roll their eyes and throw shade. Enter Amber Mariens. Played to perfection by Elisa Donovan, Amber was the overstyled, over-it snob who lived for drama. Donovan gave her just enough exaggeration to make her ridiculous, but still irresistibly fun to watch. Photo: Paramount
Honestly, her character may have accidentally inspired an entire generation of creative excuses to get out of PE. Although not wanting to get hit in the face after dropping around $20k on a new nose? Super valid. Photo: Paramount
24/50Honestly, her character may have accidentally inspired an entire generation of creative excuses to get out of PE. Although not wanting to get hit in the face after dropping around $20k on a new nose? Super valid. Photo: Paramount
After Clueless, Donovan joined the TV spin-off and kept popping up in teen-centric shows like Sabrina the Teenage Witch, where she played Morgan, Sabrina’s stylish college roommate. She also appeared in a handful of Hallmark-style movies and voice roles throughout the 2000s. Her fame didn’t skyrocket like some of her co-stars, but she stayed steady and visible. Photo: abc
25/50After Clueless, Donovan joined the TV spin-off and kept popping up in teen-centric shows like Sabrina the Teenage Witch, where she played Morgan, Sabrina’s stylish college roommate. She also appeared in a handful of Hallmark-style movies and voice roles throughout the 2000s. Her fame didn’t skyrocket like some of her co-stars, but she stayed steady and visible. Photo: abc
By the 2010s, she began moving away from the spotlight and into writing, wellness coaching, and motherhood. Donovan has since opened up about her struggles with eating disorders, and how she found peace through healing and storytelling. In 2021, she published a memoir titled Wake Me When You Leave, exploring grief, growth, and rediscovery after the loss of her father.
26/50By the 2010s, she began moving away from the spotlight and into writing, wellness coaching, and motherhood. Donovan has since opened up about her struggles with eating disorders, and how she found peace through healing and storytelling. In 2021, she published a memoir titled Wake Me When You Leave, exploring grief, growth, and rediscovery after the loss of her father.
Travis Birkenstock wasn’t supposed to be boyfriend material. He was a burnout with floppy hair and a skateboard. But Breckin Meyer turned him into the most loveable stoner in teen film history. His goofy charm, surprise sensitivity, and sweet connection with Tai made him a low-key MVP of Clueless. He was that kid in every school who had way more depth than anyone gave him credit for. Photo: Paramount
27/50Travis Birkenstock wasn’t supposed to be boyfriend material. He was a burnout with floppy hair and a skateboard. But Breckin Meyer turned him into the most loveable stoner in teen film history. His goofy charm, surprise sensitivity, and sweet connection with Tai made him a low-key MVP of Clueless. He was that kid in every school who had way more depth than anyone gave him credit for. Photo: Paramount
After Clueless, Meyer kept working steadily in both film and TV, landing roles in Road Trip and Rat Race. But he also carved out a second career in voice acting and writing. He became a key creative force behind Robot Chicken, one of Adult Swim’s most iconic shows, and voiced characters throughout its long run. He also lent his voice to King of The Hill as Joseph Gribble and wrote screenplays and pilots behind the scenes. Photo: Universal
28/50After Clueless, Meyer kept working steadily in both film and TV, landing roles in Road Trip and Rat Race. But he also carved out a second career in voice acting and writing. He became a key creative force behind Robot Chicken, one of Adult Swim’s most iconic shows, and voiced characters throughout its long run. He also lent his voice to King of The Hill as Joseph Gribble and wrote screenplays and pilots behind the scenes. Photo: Universal
Now in his 50s, Meyer pops up in indie films and streaming shows, often leaning into his comedy roots. He’s also become a regular on nostalgia-fuelled podcasts, where he talks candidly about his Clueless days and the realities of staying creative in Hollywood. And yes, he still skates.
29/50Now in his 50s, Meyer pops up in indie films and streaming shows, often leaning into his comedy roots. He’s also become a regular on nostalgia-fuelled podcasts, where he talks candidly about his Clueless days and the realities of staying creative in Hollywood. And yes, he still skates.
Oh, Elton. Tall, rich, and completely in love … with himself. Jeremy Sisto gave us the blueprint for the delusional admirer you just can’t shake. Photo: Paramount
30/50Oh, Elton. Tall, rich, and completely in love … with himself. Jeremy Sisto gave us the blueprint for the delusional admirer you just can’t shake. Photo: Paramount
From his tragic attempt at seduction in the Valley to that unhinged meltdown when Cher dared to say no to a “drive,” every woman knows an Elton. He thought he was god’s gift to Beverly Hills, and Sisto leaned into the role with every smug smirk and perfectly-placed eyebrow raise. Photo: Paramount
31/50From his tragic attempt at seduction in the Valley to that unhinged meltdown when Cher dared to say no to a “drive,” every woman knows an Elton. He thought he was god’s gift to Beverly Hills, and Sisto leaned into the role with every smug smirk and perfectly-placed eyebrow raise. Photo: Paramount
After Clueless, Jeremy Sisto has become unrecognisable. He ditched teen drama for actual drama. He made a sharp turn into crime thrillers and intense TV roles, revealing the acting range that was clearly buried under all that hair gel. You’ve probably seen him as Detective Cyrus Lupo on Law & Order, or more recently as Assistant Special Agent Jubal Valentine on FBI. He’s also voiced animated characters, taken on stage roles, and done just about everything … Go off, multi-talented king. Photo: CBS
32/50After Clueless, Jeremy Sisto has become unrecognisable. He ditched teen drama for actual drama. He made a sharp turn into crime thrillers and intense TV roles, revealing the acting range that was clearly buried under all that hair gel. You’ve probably seen him as Detective Cyrus Lupo on Law & Order, or more recently as Assistant Special Agent Jubal Valentine on FBI. He’s also voiced animated characters, taken on stage roles, and done just about everything … Go off, multi-talented king. Photo: CBS
These days, he’s more likely to be in a bulletproof vest than a varsity jacket, but we’ll never forget the guy who truly, tragically believed he and Cher were meant to be. Photo: Paramount
33/50These days, he’s more likely to be in a bulletproof vest than a varsity jacket, but we’ll never forget the guy who truly, tragically believed he and Cher were meant to be. Photo: Paramount
Tai Frasier was the new girl, the art project, and ultimately the heart of the movie. Brittany Murphy made Tai funny, awkward, loveable, and surprisingly wise at times. Whether she was appreciating Travis’ quirks or mispronouncing ‘Haitians,’ Brittany shone as the ‘virgin who can’t drive.’ It was clear from her very first scene that she was going to be a star. Photo: Paramount
34/50Tai Frasier was the new girl, the art project, and ultimately the heart of the movie. Brittany Murphy made Tai funny, awkward, loveable, and surprisingly wise at times. Whether she was appreciating Travis’ quirks or mispronouncing ‘Haitians,’ Brittany shone as the ‘virgin who can’t drive.’ It was clear from her very first scene that she was going to be a star. Photo: Paramount
Tai’s evolution from wallflower to social butterfly felt real, because Murphy played it with such heart. Even now, her performance feels timeless. Photo: Paramount
35/50Tai’s evolution from wallflower to social butterfly felt real, because Murphy played it with such heart. Even now, her performance feels timeless. Photo: Paramount
Brittany Murphy’s career soared after Clueless. She was unforgettable in Girl, Interrupted, 8 Mile, Don’t Say a Word, and voiced Luanne in King of The Hill for more than a decade. Oh, and she also starred in Uptown Girls, another movie that helped shape a generation of millennial women. Brittany wasn’t just in demand, she was the moment. Photo: MGM
36/50Brittany Murphy’s career soared after Clueless. She was unforgettable in Girl, Interrupted, 8 Mile, Don’t Say a Word, and voiced Luanne in King of The Hill for more than a decade. Oh, and she also starred in Uptown Girls, another movie that helped shape a generation of millennial women. Brittany wasn’t just in demand, she was the moment. Photo: MGM
Off-screen, she was known for her sweetness, generosity, and infectious energy. Her sudden death in 2009 shocked fans around the world. She was only 32. The loss left a gap in Hollywood that is still felt. To this day, fans and co-stars remember her as a bright light gone far too soon. Tai’s legacy, much like Brittany’s, lives on with every rewatch. Photo: Getty
37/50Off-screen, she was known for her sweetness, generosity, and infectious energy. Her sudden death in 2009 shocked fans around the world. She was only 32. The loss left a gap in Hollywood that is still felt. To this day, fans and co-stars remember her as a bright light gone far too soon. Tai’s legacy, much like Brittany’s, lives on with every rewatch. Photo: Getty
Mel Horowitz might’ve been a gruff, workaholic lawyer, but his love for his daughter was higher than his cholesterol count. Played by Dan Hedaya, Mel was the perfect foil to Cher’s extravagance, full of blunt advice and tough love. Whether he was barking at Josh or grilling Christian, Mel delivered punchlines that still land today. For a character who rarely left the house, he definitely left an impression. Photo: Paramount
38/50Mel Horowitz might’ve been a gruff, workaholic lawyer, but his love for his daughter was higher than his cholesterol count. Played by Dan Hedaya, Mel was the perfect foil to Cher’s extravagance, full of blunt advice and tough love. Whether he was barking at Josh or grilling Christian, Mel delivered punchlines that still land today. For a character who rarely left the house, he definitely left an impression. Photo: Paramount
Dan Hedaya kept the no-nonsense energy going well after Clueless. You’ve probably seen him pop up in shows like ER, Monk, and Gotham, and in films like The Hurricane and The Usual Suspects. With that trademark scowl and unmistakeable voice, he carved out a niche as Hollywood’s go-to grumpy guy. Photo: Warner Bros
39/50Dan Hedaya kept the no-nonsense energy going well after Clueless. You’ve probably seen him pop up in shows like ER, Monk, and Gotham, and in films like The Hurricane and The Usual Suspects. With that trademark scowl and unmistakeable voice, he carved out a niche as Hollywood’s go-to grumpy guy. Photo: Warner Bros
Now in his 80s, Hedaya has stepped back from acting. I bet his character would get a kick out of the Apple Watch girlies. “Do you know what time it is?” “A watch doesn’t really go with this outfit, Daddy.” A Cher line they definitely can’t relate to. Photo: Paramount
40/50Now in his 80s, Hedaya has stepped back from acting. I bet his character would get a kick out of the Apple Watch girlies. “Do you know what time it is?” “A watch doesn’t really go with this outfit, Daddy.” A Cher line they definitely can’t relate to. Photo: Paramount
Who could forget Mr Hall? Played by Wallace Shawn, he was grumpy, disorganised, and forever battling the tardy slips. But under all that chaos was a big softie. Thanks to Cher and Dionne’s matchmaking scheme, he ended up with Miss Geist and became significantly more mellow. Photo: Paramount
41/50Who could forget Mr Hall? Played by Wallace Shawn, he was grumpy, disorganised, and forever battling the tardy slips. But under all that chaos was a big softie. Thanks to Cher and Dionne’s matchmaking scheme, he ended up with Miss Geist and became significantly more mellow. Photo: Paramount
Dare I say, this might be the greatest Cupid’s play lore in cinematic history. Photo: Paramount
42/50Dare I say, this might be the greatest Cupid’s play lore in cinematic history. Photo: Paramount
Wallace Shawn is basically Hollywood’s favourite intellectual and loveable weirdo. Before and after Clueless, he was everywhere, from The Princess Bride to voicing Rex in Toy Story. He’s a writer, essayist, theatre legend, and an unmistakably unique character actor. Photo: Pixar
43/50Wallace Shawn is basically Hollywood’s favourite intellectual and loveable weirdo. Before and after Clueless, he was everywhere, from The Princess Bride to voicing Rex in Toy Story. He’s a writer, essayist, theatre legend, and an unmistakably unique character actor. Photo: Pixar
You’ll find him turning up in sitcoms like Young Sheldon, indie films, voice roles, and political interviews where he casually drops Marxist theory between takes. Honestly, Mr Hall might have been the most on-brand casting decision in the entire movie. Photo: CBS
44/50You’ll find him turning up in sitcoms like Young Sheldon, indie films, voice roles, and political interviews where he casually drops Marxist theory between takes. Honestly, Mr Hall might have been the most on-brand casting decision in the entire movie. Photo: CBS
Miss Geist, our awkward, soft-spoken queen. She was composting before it was cool to be kind to the environment. Twink Caplan brought her to life with a nervous sweetness that made you want to give her a hug, and maybe also a hairbrush. Her romance with Mr Hall was one of the most wholesome arcs in Clueless. Photo: Paramount
45/50Miss Geist, our awkward, soft-spoken queen. She was composting before it was cool to be kind to the environment. Twink Caplan brought her to life with a nervous sweetness that made you want to give her a hug, and maybe also a hairbrush. Her romance with Mr Hall was one of the most wholesome arcs in Clueless. Photo: Paramount
Twink Caplan has mostly stayed behind the scenes, but her legacy is solid. She was a producer on both the Clueless film and TV series, and later worked on the Look Who’s Talking franchise and Loser with Jason Biggs. While she hasn’t been in the public eye much, she’s been spotted at nostalgic fan events, often delightfully on-theme. Photo: Sony
46/50Twink Caplan has mostly stayed behind the scenes, but her legacy is solid. She was a producer on both the Clueless film and TV series, and later worked on the Look Who’s Talking franchise and Loser with Jason Biggs. While she hasn’t been in the public eye much, she’s been spotted at nostalgic fan events, often delightfully on-theme. Photo: Sony
Christian was hot, mysterious, fashion-forward, and completely unavailable. Cher fell hard, and honestly, who could blame her? Played by Justin Walker, he swept in with old-Hollywood charm and took Cher on the most stylish non-dates ever. It wasn’t until he turned down her ‘Betty’ energy that she realised he was gay. Photo: Paramount
47/50Christian was hot, mysterious, fashion-forward, and completely unavailable. Cher fell hard, and honestly, who could blame her? Played by Justin Walker, he swept in with old-Hollywood charm and took Cher on the most stylish non-dates ever. It wasn’t until he turned down her ‘Betty’ energy that she realised he was gay. Photo: Paramount
Justin Walker’s Hollywood run was short but memorable. After Clueless, he appeared in a few small roles before stepping away from acting altogether. He reportedly moved into the business world, running restaurants and keeping a very low profile. Photo: LinkedIn
48/50Justin Walker’s Hollywood run was short but memorable. After Clueless, he appeared in a few small roles before stepping away from acting altogether. He reportedly moved into the business world, running restaurants and keeping a very low profile. Photo: LinkedIn
Christian may have left Hollywood, but his legacy lives on. He taught an entire generation that having a weak gaydar can lead to some of your most devastating heartbreaks. Photo: Paramount
49/50Christian may have left Hollywood, but his legacy lives on. He taught an entire generation that having a weak gaydar can lead to some of your most devastating heartbreaks. Photo: Paramount
Clueless is about to be more than just a nostalgic rewatch. Cher is coming back. Alicia Silverstone is confirmed to reprise her role in a new Clueless series for Peacock, and she’s also stepping in as a producer. While most details are still under wraps, insiders say the show will reflect Gen Z culture while keeping the same biting humour and heart. No word yet on whether Dionne, Josh, or Murray will return, but one thing’s for sure … that group chat would be LIT. Photo: Paramount
50/50Clueless is about to be more than just a nostalgic rewatch. Cher is coming back. Alicia Silverstone is confirmed to reprise her role in a new Clueless series for Peacock, and she’s also stepping in as a producer. While most details are still under wraps, insiders say the show will reflect Gen Z culture while keeping the same biting humour and heart. No word yet on whether Dionne, Josh, or Murray will return, but one thing’s for sure … that group chat would be LIT. Photo: Paramount
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