7 Best And 7 Worst Moments In Clueless

Clueless, with all of its best and worst moments, was the feminist teen film we didn't know we needed. Director Amy Heckerling's now-iconic film, which debuted in theaters in 1995, surprised viewers with its witty and nuanced dialog, outstanding costume choices, and top-notch acting. Clueless also made stars out of its cast and went on to spawn countless spin-offs and reimaginings, as noted by Town & Country.

Decades later, the smart comedy is still beloved by fans everywhere — many of whom likely wish for access to Cher's closet to this day. Unlike many other films of the era, Clueless has held up remarkably well, showing just how ahead of its time it was, too. No wonder so many of us are still totally obsessed with it!

When's the last time you watched Clueless? Did you find yourself looking forward to certain scenes and cringing as you watched others? Well, we sure did. Without further ado, here are the best and worst moments in Clueless.

After exiting the vehicle of a creepy classmate, Clueless' Cher finds herself stranded in the parking lot of a liquor store in Sun Valley. Naturally, she has to phone a cab to come bail her out and take her home. But before she can complete the call on her cell, she's robbed at gunpoint. Yikes!

Cher complies with the robber when he demands that she give him her phone, and doesn't do more than moan when he takes her handbag as well. What's a bit unbelievable is that she only starts to protest when her assailant demands that she lay face down on the ground. "You don't understand," she gasps, revealing her dress to the man. "This is an Alaïa!"

While the line is pretty funny, (and yes, that dress really was an Alaïa), it's pretty unbelievable that she'd prioritize a dress over her life in that moment. For as clothing obsessed as Cher is, would she really be so cavalier as to try to bargain when there's a pistol pointed at her? That's why this scene has to be one of the worst.

One thing that becomes evident right away in Clueless is that Cher isn't a very good driver. She's so bad, in fact, that it prompts Tai to use it as an insult against her, informing Cher that she's "a virgin who can't drive." Way harsh, Tai. But, where is the lie? Cher is so inept behind the wheel that, while it's indeed comedic, it can give viewers some serious anxiety.

This is especially the case during Cher's road test, which has the instructor nearly climbing the walls of the vehicle to get out. In the span of a few minutes, a distracted Cher drives under the speed limit and outside of the lines, nearly hits a cyclist while changing lanes, and sideswipes a parked vehicle. 

While you do feel for Cher when she learns that she isn't getting her much-coveted driver's license, you may find yourself perplexed at her not understanding just how badly she failed. As such, you were probably nodding in agreement when the instructor calls himself "the messiah of the DMV" for keeping her off of the roads.

While Cher from Clueless is all about playing matchmaker for other people — which is sometimes successful and sometimes not — she admits that it would be nice to find someone for herself. Despite Cher's general rule against dating high school boys, our girl was smitten when a handsome guy named Christian strolled into the classroom for the first time.

Almost immediately, Cher puts a plan into action to bag the well-dressed new student. However, for the life of her she can't understand why he's not reciprocating her interest; she hadn't yet realized that Christian isn't interested in women. It all makes for a pretty awkward scene when Cher finally tries to put the big moves on Christian while they're laying in bed watching a movie. If only Cher had noticed that he was ogling the handsome eye candy on the screen instead of her. And when she falls off the bed while pushing her hair back? Oh Cher, we are hurting for you!

Once Cher realizes Christian is gay, the two eventually become good friends. But that attempted seduction was one of the worst moments in the film.

When viewers are first introduced to Mel Horowitz, Cher's father, in Clueless, it's clear how intimidating the man is. And while he makes good money as a litigator — a whopping $500 per hour — he's often gruff and anti-social even when he isn't working. But, of course, he's usually working — whether that means reading documents, yelling at people on the phone, or strategizing with others about a case.

However, there's something unsettling about the scene in which we first meet Cher's father. As he's walking down the stairs, the family's housekeeper notices him and promptly gasps and runs away in fear. "Lucy, our maid, is terrified of him," Cher explains. 

Look, we get it. It's meant to be funny, but if you really think about it, it's unnerving that a woman is deeply afraid of the man who employs her. Can you imagine being scared of your boss? That's why we think this is one of the worst scenes in Clueless.

If there's one thing that Cher was truly clueless about in Clueless, it's Elton's enduring crush on her. It seems that he never missed an opportunity to be close to her, eager to wrap her in his arms, never missing the opportunity to plant kisses on her. So it's no surprise that Elton persisted in being the one to drive Cher home after a party ended.

As flattering as that might be, Elton's feelings don't excuse the way he treated Cher while she was a passenger in his car in one of the worst scenes in Clueless. Upon thinking that Cher had confessed her devotion to him, Elton reaches over to try to make out with her. Confused and frankly not amused, Cher pushes him off, making it abundantly clear that she's not interested. But that doesn't stop Elton from repeatedly trying to kiss her, to the point that she gets fed up and exits the vehicle. Way to be a total creep, Elton! 

Clueless' Murray and Dionne are one of the most established couples at Bronson Alcott High School. But that doesn't mean that their relationship is without conflict, which is evident right out of the gate. And honestly? We're putting the burden of that on Murray, as he can really be a jerk sometimes.

Take, for example, one of the worst scenes in the movie: when Cher and Murray are riding with Dionne as she learns to drive. First, he laughs at Dionne when she starts her windshield wipers instead of her turn signal, then he yells at her to watch the road. And then he calls her "woman" for the umpteenth time — which Dionne has repeatedly asked him not to do — and tells her that her driving sucks.

After that he totally guffaws at Cher, who'd just confessed she nearly slept with Christian. Murray proceeds to call both Cher and Dionne "b****es." Top it all off with Murray calling Christian a "cake boy" to explain his sexual orientation and and you have a pretty good idea how lousy Murray was in this totally misogynistic moment! 

While Cher's driving in Clueless is nothing short of terrible, Dionne's driving isn't any better. This was especially apparent in the scene in which Dionne accidentally gets onto the freeway with Cher and Murray as passengers — something she's clearly never done before — and all hell breaks loose.

First, Dionne accidentally cuts off a truck while attempting to merge, then manages to get flipped off by an elderly couple. Next, a gaggle of motorcyclists come up from behind Dionne's car and go around it while cutting it extremely close. After that, a giant tractor trailer starts tailgating their vehicle, causing Murray's life to flash before his eyes.

Fortunately, Murray is able to guide Dionne off of the freeway and the trio are safely able to make an exit — but not before viewers started freaking out too. What an anxiety booster that scene is, making it one of the hardest to watch — and worst — in the entire film!