Before the nerd can get the popular girl, before the down-and-out divorcee gets his life back on track, or before the girl can get the job that will ruin her life, something needs to happen. There needs to be a quick sequence full of determination and self-improvement, brand-new clothes and beauty products. There needs to be a makeover.
The movie makeover is cinema’s most aspirational trope: a testament to the idea that you can be anything you want to be if you have the will, often the money, and the right friends. It is the purest distillation of film’s ability to transform. It is also shallow escapism, which we could use more of these days, even if it comes in morally dubious and questionably soundtracked form. It’s never not entertaining to watch an underdog protagonist dive into a makeover and come out the other side transformed.
As I did with "Getting the Gang Together" and training montages, I took in as many movie makeovers as possible and figured out which ones are the best. The process was the same: I determined the core elements of what makes movie makeovers great and then rated each entry on a scale of zero to 10 based on how well they satisfied those central principles. First, let’s go over exactly what the crucial elements of a movie makeover are:
- The Reason: There’s always an underlying motivation for the ensuing makeover, though when it comes to these montages, some of the reasons are more compelling than the rest. Sometimes, a makeover montage happens purely because one more popular, classically more beautiful person looks at another person and says, "People might like you more if you were hotter." That’s pretty shitty; makeover montages can be better than that. So, this section will be scored with that mind, rewarding the montages that are more layered and demoting the ones that equate growth with becoming attractive by societal standards.
- The Song: A good makeover montage needs a good makeover montage song that’s upbeat and youthful, and above all, fun. Makeover montages are the epitome of joyous cinematic rebirth, and the song goes a long way in setting the tone.
- The Money Spent: One of the more enjoyable things about makeover montages is how irrelevant fiscal responsibility is in them. Do you know how much salon-level products cost? Sephora sells one-ounce jars of moisturizer for like $200. But in a makeover montage, that doesn’t matter — characters make it rain credit cards on store clerks and exit boutiques with 14 overstuffed bags of clothes. It’s so thrilling and unrealistic! So: The more money characters spend within a montage, the more respect it’s going to get from me. (These monetary figures will be estimated to the closest dime, when possible.)
- The Mirror Shot: At the end of a makeover montage, there’s a moment where the character who was made over (the makeoveree?) finally gets to see what he or she looks like after all the shopping, cosmetics, and consultancies. A person’s recognition of their own ability to change is super-powerful, and the triumph of transformation is an underratedly beautiful thing to behold. (Though the montages that end with a moment of horror are compelling in their own way.) Also worth noting: The Mirror Shot doesn’t necessarily need to involve a mirror, but it doesn’t hurt.
- Bonus Points: Since makeover montages are wonderfully detailed and varied, I’ll be giving out bonus points for the random things that stick out, like funny lines, unique stylistic choices, and any innovations in makeover strategy.
Now we can get to the rankings. (Tiebreakers were determined by personal preference, don’t @ me.)
18. ‘Can’t Buy Me Love’
The Reason: Ronald Miller (Patrick Dempsey) is a classic movie dork who has saved up $1,000 to buy a telescope, because the suspenders apparently weren’t destroying his social life enough. Just when he’s about to buy the telescope at the mall, he sees Cindy Mancini (Amanda Peterson), the most popular girl in school, in distress in a nearby store. See, a friend spilled red wine on her mom’s totally boss suede dress (it was the ’80s) and — what a coincidence! — it is going to cost exactly $1,000 to replace it. At that moment, Ronald decides to abandon everything that is significant to his identity and chase the girl instead of science. He makes a deal with Cindy: He’ll pay for the dress if she pretends she’s his girlfriend for a month. What does this all have to do with a makeover? Well, before they make their debut as a couple in "the cool hallway" at school, Cindy spruces Ronald up — because no one would buy that she was going out with a dude who doesn’t rip the sleeves off of his button-down shirts. Overall, it’s kind of a sad reason for a makeover. Not only is Ronald giving up on lifelong pursuits, but he also has to go through a transformation before any of his peers accept that another human being might like his company. Then again, he’s the one who asked for all of this, so I can’t be too mad. 5/10
The Song: There isn’t one — this makeover happens in a matter of seconds. Not much time for a Duran Duran song or whatever. 0/10
The Money Spent: Cindy is an extremely efficient makeover artist — she gets the job done without spending any money at all. She makes Ronald take off his beret, throws a little mousse in his hair, untucks his shirt, rips his shirt sleeves off — don’t ask me how; this teenager must be very strong — and most importantly, she REMOVES HIS GLASSES. Without dropping a quarter, Cindy turns Ronald into Teen McDreamy. (Later in the movie, she does buy Ronald a pair of sunglasses, so let’s say the whole endeavor ran her about $25.) 2/10
The Mirror Shot: Ronald doesn’t quite sell his first walk in the cool hallway — despite the makeover, he’s still a dweeb, and he walks behind Cindy instead of next to her. No wonder one nondescript popular guy asks his nondescript popular friend, "Hey look! Who’s the dick with ears?" 5/10
Bonus Points: 2 — for Cindy’s innovation on the fly. I can’t even imagine what she’d be capable of with a budget!
17. ‘She’s All That’
The Reason: I’m sure you know how this one goes, but let’s recap: Zack Siler (peak Freddie Prinze Jr.) makes a bet with his frenemy Dean Sampson Jr. (peak Paul Walker) that he can turn any girl in their high school into prom queen. "There are 2,000 girls in this school and I could bum monkeys with every one of ’em," Zack literally says. (I guess he means sex? I was alive in the ’90s and I’m almost positive no one ever used this expression.) While smoking a cigarette, as high schoolers do, Dean picks Laney Boggs (Rachael Leigh Cook). Laney is allegedly an impossible obstacle because, as Zack puts it, "Fat I can handle; weird boobs, bad personality, maybe some sort of fungus. Scary and inaccessible is another story." First of all, this line is horrifying and just so mean. The premise of She’s All That is that Zack Siler is the all-around perfect guy — we’re told he’s the prom king and the captain of the football team, but also a man of the people with acceptance letters from every Ivy League school and a bad hacky-sack habit — but, uh, I don’t think so? He sounds like a monster to me. And from what I can tell, Laney is "scary and inaccessible" solely because she likes to paint and doesn’t like Zack. To win the bet, Zack needs to give her a makeover and make her look like someone who … doesn’t paint? Teen movies were great, but also, they were terrible. 1/10
The Song: No song! Instead, Zack’s sister Mac (Anna Paquin) and Laney just chit-chat while the former does all the makeover-ing. 0/10
The Money Spent: A bunch of makeup and a new dress? I’m guessing Zack dropped around $200 for this makeover, which is a decent amount, but nothing astounding by makeover-montage standards. 4/10
The Mirror Shot: This is the most redeemable thing about the She’s All That makeover. Laney descending the stairs to her house while Sixpence None the Richer’s "Kiss Me" plays is an iconic moment in film. Look how stunned that punk Zack is:
OK, so maybe Freddie could have played this moment a little stronger, but my opinion still stands — this is an all-time Mirror Shot. 10/10
Bonus Points: 1 — because Mac doesn’t mess up the most crucial element of a teen movie makeover and remembers to take Laney’s glasses off.
16. ‘Encino Man’
The Reason: In this modern classic, Dave (Sean Astin) finds a caveman (played by Brendan Fraser!) buried in his backyard — but still alive, contained in a block of ice. After the ice melts one day, Astin and his friend (Pauly Shore, of course) decide to clean him up and pass him off as an Estonian exchange student. Sometimes people ask, "Why don’t Hollywood studios take chances anymore?! There’s so much creativity out there!" and those people need to be reminded of 1992’s Encino Man. That said, this makeover’s reason is also valid: Who wouldn’t wanna dress a caveman up? 5/10
The Song: The makeover is scored by "I’m Too Sexy" by Right Said Fred, which is great because it’s thematically on point, and it’s just a perfect encapsulation of the era this movie was made in. 7/10
The Money Spent: Dave spends about $9.50 on Windex, Johnson & Johnson body wash, mouthwash, and toothpaste. Not much financial investment in this Ice Age makeover. 2/10
The Mirror Shot: It’s actually a mirror shot! And I really enjoy how Brendan Fraser yelps when he first sees himself as a SoCal greaseball:
And then Pauly Shore, in his way, says, "Buddy, you should be with your mug, bro. You look buff." It’s a very good moment. 7/10
Bonus Points: 0
15. ‘Love Don’t Cost a Thing’
The Reason: Love Don’t Cost a Thing is a remake of Can’t Buy Me Love; the main differences are that it stars Nick Cannon as the nerd and Christina Milian as the popular girl, the popular girl destroys an Escalade rather than a dress, and the movie is named after a Jennifer Lopez song. Most everything else is the same, along with my rating for the reason behind this makeover. 5/10
The Song: Another difference is that Love Don’t Cost a Thing’s makeover sequence is a little more elaborate. In a full-fledged montage, Paris (Milian) takes Alvin (Cannon) to the mall for a shopping spree, waxes his eyebrows; and gives him a haircut, all while "Air Force Ones" by Nelly plays. A swaggy (by 2003 standards, at least) song about buying dope shoes is a perfect accompaniment for Alvin’s makeover. 7/10
The Money Spent: $237.79 — I know this precisely because there’s a helpful shot of a cash register during the montage which reads "$231.79." Then I just added $6, because that’s about how much an eyebrow waxing costs. 4/10
The Mirror Shot: In a surprisingly subtle move, Love Don’t Cost a Thing leaves some room for mystery with its Mirror Shot. We are shown Alvin and Paris looking in a mirror, clearly satisfied with the transformation, but the viewer never gets to see what they’re looking at. That’s a nice way to try build up suspense for when you do actually get to see the Sean John’d-out Alvin for the first time. On the other hand, the final reveal isn’t that momentous. 5/10
Bonus Points: 1 — because Christina Milian teaches Nick Cannon how to do the Birdman hand rub:
It never occurred to me that learning the Birdman hand rub should be an essential part of a makeover, but now I just want to see this moment featured in every montage. She’s All That? Sure, why not?! Pretty Woman? Absolutely!
14. ‘The Devil Wears Prada’
The Reason: On the surface it’d seem that frumpy assistant Andy (Anne Hathaway) is only getting a makeover to appease her mean boss, the Devil Who Wears Prada (Meryl Streep), a woman who cares more about fashion than people. But as Stanley Tucci explains in a very compelling pre-makeover monologue, Andy’s transformation is about more than wearing nice new clothes and putting on makeup. It’s about actually caring enough about a job at a premiere fashion magazine to show a little interest in the world it covers. "You have no idea how many legends have walked through these halls, and worse, you don’t care. Because this place, where so many people would die to work, you only deign to work." It’s a very good speech, and it elevates the motivation behind this makeover. 6/10
The Song: Ugh, just a boring score. I could’ve used a Madonna song or something (which, to be fair, does happen about a scene later). 1/10
The Money Spent: Technically, Andy gets made over with clothes and products from Runway magazine’s sample closet, so it doesn’t cost anything. But for our rankings’ sake, let’s pretend she had to buy a designer poncho, a dress from Dolce & Gabbana, heels by Jimmy Choo and Manolo Blahnik, a Nancy Gonzalez purse, and a Narciso Rodriguez coat. Even a modest estimate puts that bill at around $5,800. That’s the kind of money I like to see get spent on a makeover. 8/10
The Mirror Shot: It’s great: Emily Blunt and Gisele Bundchen are talking shit about Andy when she walks in looking super-duper fly and they’re all like:
That kind of shocked expression is what makeover montages are all about. 8/10
Bonus Points: 0
13. ‘Crazy, Stupid, Love’
The Reason: Cal (Steve Carrell) is really down on himself after his wife cheats on him with Kevin Bacon. He’s legitimately pitiful: dressing terribly, moping at the bar about his impending divorce to anyone who will listen (no one will). Finally, a real cool bro named Jacob (Ryan Gosling) comes along and offers to teach Cal how to pick up women and not be such a cuck anymore. Step 1? A makeover! I’m all for the reasoning behind this one, because like Bridget Jones, Cal’s makeover is less about changing fundamental characteristics than it is learning better manners and presentation skills. And honestly, Cal could use the help. 8/10
The Song: Oh no, it’s a jazz song! Do all Ryan Gosling movies just suddenly turn into La La Land now? [Turns on Drive.] OH GOD. 2/10
The Money Spent: Cal and Jacob go in at the mall: He buys at least three button-downs, at least three ties, sunglasses, a sweater, cologne, and jeans, and they take a trip to a salon. Cal’s total was definitely in the thousands, and he probably maxed out a credit card. That’s the kind of spending I like to see! 7/10
The Mirror Shot: It’s only OK — as Cal emerges from a dressing room, a cute hairstylist says, "Wow, look at you!" That sounds nice and all, but I suspect this woman is only lobbing out compliments because the customer is always right. She might as well have said, "Wow, you were an old ugly man — now you’re still old, but slightly less ugly!" 6/10
Bonus Points: 1 — for when Jacob tells Cal, "Be better than the Gap." I don’t endorse Jacob’s denigration of the Gap — it’s a fine store with reasonably priced khakis — but I do find this line to be beautifully motivational. It’s less about the Gap and more about reaching beyond what your damaged self-esteem tells you that you deserve. This concludes my close reading of a five-word line from Crazy, Stupid, Love.
The Reason: I first saw Jawbreaker when I was 10 years old, which in retrospect was probably not something I should have been allowed to do. Case in point: In this movie, a nerdy girl named Fern (great nerd name) walks in on the popular girls trying to arrange the body of their popular friend, who they have accidentally murdered. In exchange for Fern’s silence, the leader of the clique, Courtney (Rose McGowan), offers to give her a makeover and let her be popular. Watch Courtney convince Fern to let them do this to her, it’s very creepy:
In all honesty, though, covering up a fictional homicide is an excellent, if extremely dark, reason for a makeover. 9/10
The Song: It’s less of a song, and more of a series of eerily ethereal sounds while multiple characters recite a poem that includes the line, "For the hair of a dead girl, we use model glue." This movie is seriously messed up, but it at least knows its voice. 6/10
The Money Spent: A new dress, a bunch of makeup, professional hair styling by a man who seems to work a funeral home — Fern’s makeover costs somewhere around $200, which is just below this list’s average. 4/10
The Mirror Shot: Jawbreaker’s Mirror Shot is an entirely separate scene where Fern and her new "friends" strut down the school hallway while "Yoo Hoo" by Imperial Teen plays. It’s a memorable sequence, but it’s quite drab, and it lacks any of those classic moments of shocked recognition. 5/10
Bonus Points: 1 — for being so god damn trippy. If you can’t tell, this movie shook me to my core.
11. ‘13 Going on 30’
The Reason: Some magic dust falls on 13-year-old Jenna Rink (Jennifer Garner) and the next thing she knows she’s 30. Before going out one night, she goes all out and gives herself a makeover. There isn’t really a reason behind it, other than Teen Jenna wanting to enjoy all of the beauty products and clothes Adult Jenna has. But that’s fine. The impulse makes perfect sense to me, because when I watched Big as a kid I was like, "Of course you gotta put a trampoline inside a New York City apartment!" This is basically the same thing. 7/10
The Song: Whitney Houston’s "I Wanna Dance With Somebody" is going to get a perfect score from me every day of the week, no matter what montage it’s scoring. That is all. 10/10
The Money Spent: Jenna already owns all of the stuff she uses for her makeover. That’s the point, though it doesn’t help the movie’s point total. 1/10
The Mirror Shot: The montage ends with Jenna riding an elevator with an actual teenage girl, who gives Jenna a bunch of compliments. When she says she likes Jenna’s dress, Jenna grabs her chest and vigorously replies, "That’s because I’ve got these incredible boobs to fill it out!" It’s a real nice moment. 7/10
Bonus Points: 0
10. ‘Captain America: The First Avenger’
The Reason: To win World War II and defeat the Nazis, who have taken possession of a powerful weapon called the Tesseract, the USA turns to Steve Rogers, a man with a big heart who loves his country. The only problem is, Steve is real shrimp — he’s so tiny that it almost doesn’t make sense how his head is attached to his body. The guy needs a makeover. Like, a big one: He needs to be locked in a chamber and injected with a ton of mega-steroids developed by Stark Industries. This is a very good reason for a makeover — the stakes are unprecedentedly high. I believe Captain America is the only movie ever to employ the makeover as a means to winning a world war. 9/10
The Song: It’s all just sweeping strings; dramatic and rote, just like Captain America. 2/10
The Money Spent: No one actually says how much Steve’s transformation is going to cost the government, but I’m going to go ahead and assume that in 1942, technology that can turn a pipsqueak into an invincible he-man with giant, glistening muscles would cost like half of the defense budget. 10/10
The Mirror Shot: Hahaha. I think the movie wants you to be impressed by this image …
… but I just can’t stop laughing. Why is Chris Evans so shiny!! Why do his khakis still fit?! 4/10
Bonus Points: 0
9. ‘Bridget Jones’s Diary’
The Reason: Bridget (Renée Zellweger) has been flirting with Daniel, her saucy boss at work (Hugh Grant with a hockey player’s haircut). An upcoming book launch party is going to be the first time they’re out together since Daniel told Bridget, "Like your tits in that top," so she needs to be on her game. This is an extremely real, if not entirely HR-appropriate, reason for a makeover; it’s not like she’s changing everything about herself, she’s just going the extra mile to present the best version of herself. Anyone who’s been on a Tinder date can surely relate. 7/10
The Song: It’s a song that sounds like the Mission: Impossible theme, which perfectly underscores how seriously we all take an endeavor like Bridget’s. While all of Bridget’s friends explain what she needs to do to bag this guy, this song plays, and for a few minutes Bridget Jones’s Diary feels like a heist movie. 7/10
The Money Spent: The only new purchase Bridget appears to make is on a Nair waxing kit ($5), so not much to celebrate there. 2/10
The Mirror Shot: During this makeover/getting ready montage, a voice-over from Bridget makes an insightful aside about her choice of underwear. If she wears a sexy thong, by her luck nothing will happen with Daniel, and she will have spent an entire night with a wedgie for no reason. But, if she wears granny panties, it’ll basically guarantee that she and Daniel will hook up, at which point she can explain away her ghastly choice of undergarments. That little moment of contemplation is the perfect setup for Bridget Jones’s Mirror Shot, in which Bridget emerges from the London Underground clutching at her waist, trying to adjust the gigantic underwear she has on. This movie’s awesome, guys. 7/10
Bonus Points: 2 — because this movie employs the classic montage style to perfection. The way the movie cuts back and forth between Bridget’s friends giving her advice and Bridget actually taking that advice is incredible. Formally speaking, there isn’t much difference between this makeover montage and the "Getting the Gang Together" montage in Armageddon.
8. ‘The House Bunny’
The Reason: The nerdy, socially awkward ladies of Zeta Alpha Zeta are the campus laughingstock. So much so that they can barely get girls to pledge their sorority — which is a problem, because if they can’t get pledges, they can’t pay the mortgage on their house, and if they can’t pay the mortgage on their house, the cooler sorority Phi Iota Mu is going to buy it and … drive them to homelessness? I don’t think that’s how Greek life works, but anyway, a former Playboy Playmate named Shelley (Anna Faris) becomes ZAZ’s house mom and figures out the best way to make the sorority girls more inviting: mass makeovers. It’s one of those iffy reasons for a makeover: On one hand, the message is basically that these girls need to more closely adhere to mainstream culture’s ideas of beauty and normalcy in order to be found attractive by the opposite sex; on the other hand, this could be seen as commentary on the regressive environment of fraternities and sororities, which I absolutely support. So let’s just cut this down the middle, shall we? 5/10
The Song: It’s "Girlfriend" by Avril Lavigne, which is just edgy enough to score a sequence featuring outcasts going to a salon. And it’s thematically relevant: "Girlfriend" is about stealing a guy’s attention away from a more traditional girl, and that’s exactly what the ladies of ZAZ are setting out to do. 7/10
The Money Spent: Since there are at least six girls who get a makeover in House Bunny, the expenses are nice and high: about $4,780 for heels, a bevy of Sephora products, makeup mirrors, salon hair treatments, and clothes, as well as a good $2,000 for painting the ZAZ house and resodding the lawn. 8/10
The Mirror Shot: The House Bunny’s Mirror Shot has all the girls, arms linked, strutting through campus in slow motion while every man’s jaw detaches from their skulls. It’s styled like a scene from a Michael Bay movie: gaudy, over the top, and awesome:
Bonus Points: 0
7. ‘The Princess Diaries’
The Reason: Teen Mia Thermopolis (Anne Hathaway, the queen of movie makeovers) finds out on her 16th birthday that she’s actually a princess! Only problem is she’s awkward, generally unkempt, and woefully ill-mannered. "I’m actually royalty" is a pretty solid reason for a makeover: Not only is it extremely glamorous, but it would be extremely necessary. Imagine you just found out that you’re part of a country’s most important family — you’d wanna get your hair cut, too. 7/10
The Song: I was convinced The Princess Diaries was going to have a great makeover montage song — it’s a Disney movie for crying out loud! Alas, it does not, instead opting for a refined, stately score. 2/10
The Money Spent: Mia’s grandmother (Julie Andrews) hires a consultant named Paolo (Larry Miller) to do the makeover. There’s no mention of what Paolo’s fee is, but considering that he’s being used by royalty, I’d imagine he’s pretty costly. And he has two employees! This makeover job cost at least five figures. 9/10
The Mirror Shot: A very good one, because it involves Paolo’s assistants holding two giant photos of the old Mia up to her face and then separating them to reveal the new Mia.
It’s a really nice touch that creates a moment of anticipation while also helping you to remember exactly what Anne Hathaway looked like before they straightened her hair. 7/10
Bonus Points: 2 — for the jokes Paolo makes about Mia’s eyebrow. They’re both pretty solid: "I love your eyebrows. We’ll call them Frida and Kahlo," and "If Brooke Shields married Groucho Marx, that child would have your eyebrows."
6. ‘Dumb and Dumber’
The Reason: Two extremely stupid men, Harry (Jeff Daniels) and Lloyd (Jim Carrey) have traveled to Aspen, Colorado, to return a briefcase to Mary Swanson, a woman they barely know (Lloyd drove her to the airport and immediately fell in love with her). By chance, they read in the newspaper that Mary is hosting a gala for endangered birds. "Well, go on, Cinderella, we’ve gotta get you ready for the ball!" Harry tells Lloyd. Needing to clean up for a special occasion is a pretty basic reason for a makeover montage, but Dumb and Dumber gets a slight bump because these two idiots’ plan is so half-baked that it’s hilarious. 6/10
The Song: The movie uses "Oh, Pretty Woman" by Roy Orbison, a rather genius nod to one of the great makeover montages in film history, which you will read about if you keep scrolling. The contrast between the song and Jim Carrey getting his disgusting toe nails sawed down with a power tool is amazing. 8/10
The Money Spent: Harry and Lloyd go in, dropping an estimated $1,200 on new tuxedos, spa treatments, and haircuts. Of course, they don’t really mind how much money they spend, because they’ve been borrowing from the millions in Mary Swanson’s briefcase and replacing the money with IOUs. 6/10
The Mirror Shot: You can’t tell me you don’t love it when Jim Carrey emerges in a ridiculous orange tuxedo, happy as a clam, to riotous applause from Jeff Daniels. 7/10
Bonus Points: 1 — because I will always laugh when Lloyd uses the ketchup packet to make a barber think he’s accidentally cut Lloyd’s throat.
5. ‘Mrs. Doubtfire’
The Reason: After a nasty custody battle, Daniel Hillard (Robin Williams) determines that the only way to spend more time with his kids is to be their nanny. Of course, his ex-wife, Miranda (Sally Field), isn’t just going to hire him; he needs to impersonate an elderly European woman to get the job. He’s good at doing voices, but he needs some help with the whole "looking like a woman" thing. Daniel’s life would have admittedly been much easier if he didn’t throw his son a raucous birthday party and didn’t drive Miranda to file for divorce, but come on, we’re past that now. The guy wants to get a makeover so that he can be with his children. Is there a sweeter reason for one of these montages out there? 9/10
The Song: "Luck Be a Lady" by Frank Sinatra … GET IT???? 6/10
The Money Spent: Daniel’s showbiz friends go through a ton of practical effects to turn him into Mrs. Doubtfire: latex prosthetics, foam facial casting, fat suits, and so on. They probably didn’t charge him full price for any of that stuff, but a cursory internet search tells me that even on the cheaper end, that kind of makeup costs about $400. A good bit of money, but still, sort of a bargain when you think about it. 5/10
The Mirror Shot: Daniel asks his makeup friends if he looks close to an old lady. One of them says, "Any closer, you’d be MOM." Then they celebrate:
It’s so wonderfully joyous and triumphant! This is one of those scenes that feels less like a scripted movie moment and more like a snapshot of unfiltered human emotion. I love it. 8/10
Bonus Points: 0
The Reason: Basically, Cher (Alicia Silverstone) has developed a conscience and discovered how much joy she takes in helping people in ways that also help her. So after kinda-sorta tricking two teachers into hooking up, Cher turns her benevolence toward Tai (Brittany Murphy), a new student who wears clothes that make her look like a farmer, and decides to befriend her and give her a makeover. On one hand, it is really nice of Cher to take an outcast under her wing. Then again, Tai is just a girl who likes to smoke pot and hang out with skaters; the whole Barbie thing is really forced on her. But then, on an entirely different hand, Clueless is a satire and is deftly pointing out the inherent absurdity of the classic concept of a makeover. So: 6/10
The Song: The entire Clueless soundtrack is perfect. The mix of alternative ’90s rock, pop, and hip-hop defines the movie’s aesthetic and captures teen life in Southern California so well. "Supermodel" by Jill Sobule, the song that plays during Tai’s makeover, is just par for the course. The self-aware lyrics about aspirational beauty and the upbeat, electric-guitar-driven music is a microcosm of Clueless, a movie that both celebrates and satirizes teenage girls. 10/10
The Money Spent: You’d think as a resident of Beverly Hills, Cher would break the bank on making over Tai, but she does it cheaply. Other than a few bottles of shampoo and some makeup (about $100), Cher uses only things she already owns. Daddy would be proud. 3/10
The Mirror Shot: There are so many mirrors, and Tai is just so happy with how the makeover has turned out. This is what a good Mirror Shot should be. 8/10
Bonus Points: 2 — because the makeover goes on long after the montage is over, with Cher forcing Tai to work out to Cindy Crawford and teaching her the word "sporadic."
3. ‘Legally Blonde’
The Reason: Elle Woods (Reese Witherspoon) got into Harvard to follow her boyfriend, Warner, and prove to him that she wasn’t too ditzy or stupid or whatever words he used when he reduced her down to a stereotype. Apparently that wasn’t enough: Everyone at Harvard spends the first half of Legally Blonde demeaning Elle, as if she didn’t graduate high school with a 4.0 and also get into Harvard. After Warner — who gets a new girlfriend, by the way — tells Elle that she’s "not smart enough" to get an internship, she goes into FU mode and sets out to get good grades, get that internship, and prove the haters wrong. This is kind of a reverse makeover montage, where the pretty girl becomes a bookworm instead of the other way around. And it’s got a great reason behind it: Warner and all the Harvard snobs deserve to be shut up. 9/10
The Song: "Watch Me Shine" by Joanna Pacitti isn’t exactly a megahit jam, but the song’s production style cloaks Legally Blonde in early-2000s nostalgia, and the lyrics are extremely on topic. The title is "Watch Me Shine," which practically sounds like a line out of Elle Woods’s mouth. 7/10
The Money Spent: Elle Woods buys an iMac laptop (one of those awesome, clam-shell ones) and a bunch of textbooks for this makeover. Not cheap, probably like $2,500. 7/10
The Mirror Shot: It’s extremely satisfying to see the look on everyone’s faces when they see Elle doing school:
"Is she carrying books?" one dude murmurs. Yeah man, she is! She goes to Harvard JUST LIKE YOU. And she’s attractive! That you can’t wrap your mind around this concept is way more concerning to me. 7/10
Bonus Points: 1 — because I really like that quick shot of Elle’s chihuahua falling in love with the Taco Bell dog.
2. ‘Miss Congeniality’
The Reason: To stop a terrorist attack! Tomboy FBI agent Gracie Hart (Sandra Bullock) needs to become glamorous and pretty so she can infiltrate the Miss United States beauty pageant and catch a terrorist before they set off a bomb during the telecast. Next to Captain America, this is the best reason ever for a makeover. 9/10
The Song: Unfortunately, it’s all just a generic, patriotic-sounding score. Miss Congeniality could have been the best makeover montage of all time if it had a fun soundtrack. 2/10
The Money Spent: First off, the Miss United States people hire legendary pageant coach Victor Melling for Gracie, which can’t be cheap. And on top of that, Gracie goes through a crazy amount of makeup and hair-styling procedures. FBI definitely footed the bill, and I’m sure it ran them over $10,000. 9/10
The Mirror Shot: Does a Mirror Shot get any better than this one?
No, I don’t think it does. If you ever have the chance to walk out of an airplane hangar while "Mustang Sally" by Wilson Pickett plays and look so good that you make a misogynist whip off his sunglasses like he’s David Caruso in CSI: Miami, I recommend you do that. 10/10
Bonus Points: 1 — for length. The makeover montage in Miss Congeniality is almost five minutes long, which is impressive and unmatched.
1. ‘Pretty Woman’
The Reason: Edward (Richard Gere) needs a woman who can accompany him on fancy business dinners. He really likes this one girl, Vivian (Julia Roberts), who seems to get him and respect his boundaries. The thing is, in her capacity as a sex worker, she wears clothes that make rich white people have seizures. So Edward offers to pay Vivian for a week and buy her a wardrobe of tasteful clothing if she goes to these dinners with him. I’ll admit that the reasoning behind this makeover — go buy some new clothes and fix yourself up because everyone is staring — isn’t the greatest. But not all romances start in a flower bed. 4/10
The Song: "Oh, Pretty Woman" by Roy Orbison in Pretty Woman is an iconic music-in-movies moment. The two go hand-in-hand. When you hear the opening notes to this song, it’s impossible not to see Julia Roberts’s face, which is a strong testament to the impact of this musical choice. 9/10
The Money Spent: Vivian more or less opens a tab at every store on Rodeo Drive during this montage. By the time she’s done, she’s walking into a hotel wearing a new dress and carrying about six other bags filled with designer clothes. Speaking of … 9/10
The Mirror Shot: When hotel concierge Barney Thompson, who’s been helping Vivian class herself up, sees her transformation, he smiles in way that seems so filled with pride:
That subtle reaction helps you understand that Vivian’s makeover is about more than just an escort successfully posing as some wealthy guy’s girlfriend. She’s gained a new sense of self and confidence, and he can feel it. It’s a beautiful moment. 7/10
Bonus Points: 3 — for the moment when Vivian schools a stuffy store clerk who previously tried to flex on her because she wasn’t fancy enough for this upscale Beverly Hills boutique. Watch this. It’s so vicious:
As if the "Big mistake. Big. Huge!" line wasn’t enough, Vivian throws in "I have to go shopping!" as she’s exiting the store. This is the most anyone has ever been owned in a movie, and I’m including Daniel Plainview’s "Milkshake" speech in There Will Be Blood.
An earlier version of this story misidentified the city Harry and Lloyd travel to in Dumb and Dumber. It is Aspen, not Denver.