Throwback Thursday: The Top 40 Teen Comedies of All Time, Part One (40-31)

By on July 10, 2014
Courtesy of Miramax Films

Hello, and welcome to a new feature we’re trying out here at the Kaleidoscope! Every Thursday, I’ll be tackling a list of my all-time favorites in a particular genre, be it movies, television, literature or music. As tends to be the case with lists of this nature, the lists will be entirely subjective, and purely my own opinions. That said, by all means send me your own lists via the comments section and we can compare and contrast!

For my first list, I’ll be tackling one of my personal favorite subgenres: the teen comedy. The rules are simple: it needs to prominently involve teenagers, be funny, and focus primarily on the high school years. That means no college-era comedies, a la “Animal House,” “Revenge of the Nerds,” “Neighbors,” et al. (Hopefully, we’ll get to those in time.) Also out by default are movies like “Rebel without a Cause,” “The Outsiders,” “The Squid and the Whale,” etc. – being as how they’re not exactly a barrel of laughs.

As tends to be the case, we’ll start at the bottom and work our way up the list, week by week, starting at number 40. We’ll also be doing ten per week, so as to allow myself a little more wiggle room to talk about what the films are about and why I chose them. Be sure and click on the film titles for the trailers if the flicks seem interesting and you want to see more. Now that you know the essential rules, let’s get started with the countdown!


Tobey Maguire and Reese Witherspoon try and get their color on in "Pleasantville." Courtesy of and New Line Cinemas.

Tobey Maguire and Reese Witherspoon try and get their color on in “Pleasantville.”
Courtesy of and New Line Cinema.

40. Pleasantville (1998)

It seems wholly appropriate to begin with a movie that quite literally bridges the gap between the old and the new, the past and the modern age. The story begins with twin siblings David (then-future “Spider-Man” Tobey Maguire) and Jennifer (pre-“Legally Blonde” Reese Witherspoon) fighting over the TV remote, which breaks and necessitates the involvement of a repairman (the legendary Don Knotts, of “The Andy Griffith Show”). He gives them a new one which, in true “Twilight Zone” form, actually transports them into the show David loves, the 1958 retro-comedy “Pleasantville,” hence the title.

As the teens attempt to navigate their way through the largely alien landscape, they also, a la “Back to the Future,” have an unavoidable effect on their surroundings. As they try to find their way back to their time, their interaction with the people of the sitcom changes both the siblings and the denizens of the show. This results in some fun humor that shows both how the more things change, the more they stay the same, and how different eras have different advantages- and drawbacks.

Aside from the inherently clever premise, what makes this work is the enormously talented cast, which includes lost of familiar faces, some before they were well-known. The big names at the time were Jeff Daniels (“Dumb and Dumber”), William H. Macy (“Fargo”) and Joan Allen (the “Bourne” series); but the film also features future names like the late Paul Walker (the “Fast & the Furious” series), Jane Kaczmarek (who went onto to play the mom on “Malcolm in the Middle”), Marley Shelton (“Grindhouse”), Marissa Ribisi (sister of Giovanni, “Dazed & Confused”), Jenny Lewis (the singer/songwriter, formerly of Rilo Kiley), Giuseppe Andrews (“Cabin Fever”), Jason Behr (“The Grudge”), Maggie Lawson (“Psych”), and Marc Blucas and future Emmy-winning screenwriter Danny Strong (“Game Change”), both from the TV version of “Buffy the Vampire Slayer.”

Written and directed by “Hunger Games”-helmer Gary Ross, it’s a lot of fun, and the unique melding of color and black & white cinematography makes it a visual feast of the sort we rarely see these days. In short, it perfectly captures the divide between now and then in a very clever, fun way, without forgetting to acknowledge the imperfections of both. That makes it one of the best teen comedies ever, in my humble estimation.

39. The New Guy (2002) The New Guy

As a bit of a geek myself, nerd wish fulfillment tales are a big draw for me personally, and they don’t come much nerdier than DJ Qualls (“Hustle & Flow,” “Supernatural”). Here, he plays the oddly-monikered Dizzy Gillespie Harrison, who gets himself expelled from high school on purpose, in order to start over at a new school. With the help of Luther (Eddie Griffin, the “Undercover Brother”), who he meets after a heavily-medicated incident lands him in jail, he rebrands himself as rebel and soon makes a name for himself at the new school.

What makes this film so fun, in addition to the novelty of Qualls as a decidedly unlikely leading man, is the host of familiar faces on display. There’s “New Girl” Zooey Deschanel as Qualls’ band-mate in a funk rock group (!), former “Buffy the Vampire Slayer” and “Dollhouse”-vixen Eliza Dushku as his love interest (!!), singer Lyle Lovett (TV’s “The Bridge”), perfectly-cast as his father; and Illeana Douglas (“Cape Fear”) as a teacher.

Plus, there’s a host of cameos from everyone from Jerry O’Connell (“Scream 2”) to former Black Flag singer Henry Rollins to skateboarder Tony Hawk to “SNL” star Horatio Sanz. Still not enough? There’s also “KISS”-man Gene Simmons, “Tenacious D” co-member Kyle Gass, rappers Kool Mo Dee and Vanilla Ice, and-heart be still- the “Hoff” himself, “Baywatch”-star David Hasslehoff. Now that’s a cast!

Okay, so the overall film is fairly predictable, but then, so are most teen films. That’s kind of part of their charm. But if you can’t get behind a film that casts someone like Qualls as the cool guy in school, I’m not sure we have much to talk about. It may be a bit on the slight side, but it’s a lot of fun, and the energy of the film is infectiously endearing. By all means, if anyone in the impressive cast grabs your attention, you probably won’t be disappointed.

Just One of the Guys38. Just One of the Guys (1985)

As you will see, I have a particular affection with 80’s-era teen flicks, which remain among the best of the bunch. Here’s one of the more overlooked and underrated ones. It stars the shoulda-been-a-contender Joyce Hyser, who also crops up in another 80’s teen favorite, “Valley Girl” and the classic rock-mockumentary “This is Spinal Tap.”

She plays Terry Griffith, a teen journalist who feels slighted by her employers, thinking it’s because of her looks and gender. After failing to get a dream internship, she decides to take matters into her own hands and go deep undercover as a boy at another high school, intending to write about the experience and expose the different was boys are treated from girls.

If this sounds familiar, it’s because it’s basically a variation of Shakespeare’s “Twelfth Night,” which also served as the inspiration for the Amanda Bynes vehicle “She’s the Man,” which basically substituted reporter with soccer player and went from there. Despite the lack of well-known names, it does feature some familiar faces, including then-future “Twin Peaks” sex symbol Sherilyn Fenn as a girl who crushes on Griffith, not knowing she’s a he; TV-guest star regular Clayton Rohner (whose “April Fool’s Day” GF, Deborah Goodrich also crops up) as her best friend at her new school that she crushes on big time, leading to some obvious problems; 80’s bad guy supreme Billy Zabka (“The Karate Kid” series) as-what else?- a bully; “Castle” M.E. and “Ellen” co-star Arye Gross; and an amusing turn by Billy Jacoby (“The Beastmaster”) as Griffith’s younger brother, who teaches her to be more guy-like.

It’s a lot of fun, and makes some nifty, still relevant points about gender roles and sexism, making it sort of the rare teen movie that doubles as a feminist statement. Although, perhaps somewhat tellingly of the times, it still features some fairly gratuitous nudity, if somewhat earned by the nature of the plot- hence the PG-13 rating. If you can get past the admittedly dubious premise, it’s a fun watch that still holds up well to this day.

37. She’s All That (1999)

One of my dream girls from my own high school days, the still lovely Rachael Leigh Cook, post-makeover in "She's All That." Courtesy of

One of my dream girls from my own high school days, the still lovely Rachael Leigh Cook, post-makeover in “She’s All That.”
Courtesy of

Okay, full disclosure before you balk: I had a massive crush on star Rachael Leigh Cook (“Perception”), which has remained to this day, so I may be a little biased when it comes to this one. To make matters worse, my biggest crush of the 90’s era was “Buffy”-star Sarah Michelle Gellar, who crops up in a cameo- her and star Freddie Prinze, Jr. were dating at the time and would go on to get married- and the film also features two other lovely ladies I’m quite fond of: then-future “Rogue” Anna Paquin (also of “True Blood”) and Jodi Lyn O’Keefe (“Prison Break,” “Hit the Floor”), who really should have been a bigger star. So, yeah, it’s a total hottie overload, as far as I’m concerned.

But lest you think my own teenage hormones were solely responsible for this making the list, it’s also a surprisingly durable teen comedy that still holds up to this day, thanks to a smarter-than-you’d-expect script co-written by, of all people, then-future would-be Hitchcock heir apparent M. Night Shyamalan, of “The Sixth Sense” fame. As with the last entry, this one also has roots in classic literature, in this case, playwright George Bernard Shaw’s “Pygmalion,” which some of you may know better as the source for the classic flick “My Fair Lady.”

If you’re not familiar with either, you’ve certainly seen at least one movie/TV show with a similar plotline. To wit, a popular person- in this case Zack (Prinze)- bets a friend, Dean (Paul Walker), that he can transform any girl in school into Prom Queen material after getting dumped by Queen Bee popular girl Taylor (O’Keefe) for a former reality-TV star (Matthew Lillard, who would go onto co-star as “Shaggy” to Prinze’s “Fred” in the “Scooby Doo” movies). Faster than you can say “Makeover montage!” he does just that, but finds himself falling for her in the process, but of course.

Yes, the story’s a bit clichéd, and Cook is clearly a hottie from the jump- albeit admittedly in dire need of said makeover (which would later be hilariously sent up in the spoof “Not Another Teen Movie”)- but the cast is top-notch, and also includes singer Usher, rapper-and-future Nicki Minaj template Lil’ Kim; “Home Alone” little bro Kieran Culkin (“The Cider House Rules”); Gabrielle Union (“Think like a Man”), Dulé Hill (“Psych”), Milo Ventimiglia (“Heroes”), Kevin Pollak (“The Usual Suspects”) Clea DuVall (“American Horror Story: Asylum”) and “Animal House” alum Tim Matheson. All that- no pun intended- and an absolutely bonkers dance sequence at the end set to Fatboy Slim’s “The Rockafeller Skank” make this a cut above the rest, IMHO.


Julia Stiles and the late Heath Ledger make a love connection in "10 Things I Hate About You." Courtesy of

Julia Stiles and the late Heath Ledger make a love connection in “10 Things I Hate About You.”
Courtesy of

36. 10 Things I Hate About You (1999)

From the same year as the previous entry, this is yet another variation of a classic Shakespeare tale, in this case, “The Taming of the Shrew.” It just goes to show that the old classics are just a makeover away from new successes- much like a lot of these film’s heroes and heroines. Also as with many films on this list, this one boasts a better-than-average cast, including the breakthrough performances for three of the leading actors, all of whom would go onto to even bigger success: Julia Stiles (“Silver Linings Playbook”), Joseph Gordon-Levitt (“Don Jon”), and the legendary Oscar-winning Heath Ledger, of “The Dark Knight” fame.

Levitt plays Cameron, a teen new in school with a crush on popular girl Bianca (Larisa Oleynik, of “The Secret World of Alex Mack” fame). The problem is, as per the established rules of her father (stand-up comedian Larry Miller), she can only date if her older sister, Kat (Stiles), an introverted outcast, finds a boyfriend first. Thus, it is up to Cameron, with an assist from pal Michael (David Krumholtz, “Numb3rs”) to find a mate for the original grumpy Kat, which he does in the rebellious Patrick (Ledger), whom he pays to date her, which, naturally, later becomes an issue.

Featuring last entry-star Gabrielle Union (see also “Bring It On”), Andrew Keegan (“Party of Five”), Daryl “Chill” Mitchell (“Galaxy Quest”), and the multi-award-winning actress Allison Janney (“Masters of Sex”), this one is helped immeasurably by a winning cast, in particular Ledger, who does a show-stopping, memorable rendition of “Can’t Take My Eyes Off of You” to woo Stiles’ character; and a winning script by Kirsten Smith and Karen McCullah Lutz, who would go on to script the hits “Legally Blonde,” “Ella Enchanted” and “The House Bunny,” among others.


These cheerleaders aren't the ones you want to aspire to, in "Sugar & Spice." From left: Marley Shelton, Melissa George, Mena Suvari, Sara Marsh, Rachel Blanchard and Alexandra Holden. Courtesy of and New Line Cinema.

These cheerleaders aren’t the ones you want to aspire to, in “Sugar & Spice.” From left: Marley Shelton, Melissa George, Mena Suvari, Sara Marsh, Rachel Blanchard and Alexandra Holden.
Courtesy of and New Line Cinema.

35. Sugar & Spice (2001)

Despite the frothier nature of the previous entries, I tend to skew a little darker for most of my teen comedy favorites. Here’s a great example of that kind of film. Marley Shelton, who also cropped up in number 40, as well as the likes of “Never Been Kissed” and “Scream 4,” plays a popular high school cheerleader, Diane, who finds herself pregnant by, naturally, star quarterback Jack (James Mardsen, of the “X-Men” movies). Yes, that makes them Jack & Diane, my older readers, so you can insert said song here.

Moving out of their respective parents’ homes and into one of their own, they are struggling to make ends meet while finishing out high school when she has the bright idea to commit the perfect crime: robbing a bank. Recruiting her fellow cheerleaders, Kansas (Mena Suvari, “American Pie”), Cleo (Melissa George, “Alias”), and Hannah (Rachel Blanchard, “Fargo”); the group hilariously research every heist movie they can get their hands on, including “Reservoir Dogs,” “Heat” and “Point Break” as they plan their own. Things go from there, with the expected- and often unexpected- amusing results.

Featuring some nifty cameos from Jerry Springer, MTV Newsman Kurt Loder, and talk show host Conan O’Brien, who serves as the obsessive object of one of the girl’s affections (!), the film also co-stars Marla Sokoloff (“The Practice”) as a jealous rival of the girls; Alexandra Holden (“Rizzoli & Isles”) as the daughter of their gun supplier (W. Earl Brown, of “Deadwood”); and Sean Young (“Blade Runner”) as a teacher, plus a score by 80’s icon Mark Mothersbaugh, of Devo fame, who also scored more than a few of the other films on my extended list. It may not be everyone’s cup of tea, but I really liked it and think it’s one of the more underrated teen comedies out there, and it certainly features a more left-of-center plot than most.


Jamie Lee Curtis and Lindsay Lohan are having one "Freaky Friday." Courtesy of

Jamie Lee Curtis and Lindsay Lohan are having one “Freaky Friday.”
Courtesy of

34. Freaky Friday (2003)

Believe it or not, current generation, there was a time when former child star Lindsay Lohan made movies worth seeing, and not just the obvious choice “Mean Girls.” Take also, for instance, this fun remake of the 70’s Disney classic, which originally featured Jodie Foster in the lead. Disney teen flicks can be awfully hit-or-miss (or just plain awful), but they got this one right, stripping the original of some of its more dated and silly elements and ably updating it for a new generation to great effect.

You’ve seen the basic plot before: a teen and her mother each wish that the other could walk a mile in their shoes and just that happens, as mother and daughter switch bodies and are forced to live out their lives as an adult or teen until they can find a way to reverse the process. Helped immeasurably by a surprisingly-game Jamie Lee Curtis (the original “Halloween”) as the mother, this was the film that helped launch Lohan’s career into the stratosphere, which she then cemented with “Mean Girls” the year after.

Astonishingly enough, Curtis was only hired four days before shooting, replacing Annette Bening on the fly. Kelly Osbourne was also supposed to play Lohan’s character’s best friend, but had to drop out as well. Furthermore, Lohan’s character was originally supposed to be a Goth type, which she herself balked at, opting to make her a rocker chick instead. With all of this going against it, you’d think the movie would be bit of a train wreck, but Curtis and Lohan complement each other perfectly and Curtis, in particular, nails her role, making this the rare teen film in which the main teen is actually overshadowed by the main adult. To be sure, the original is worth seeing, but this one is the superior take, IMHO.

Porkys33. Porky’s (1982)

Okay, okay, stay with me on this one and listen to my logic before you object. Yes, the film is exploitative and oft-politically incorrect, but it was also the film that paved the way for countless others in its wake of a similar bent, from “Losin’ It” to “American Pie” to pretty much any other movie that revolves around horny teenagers trying to lose their virginity since- and that’s not a small amount of movies, my friends. It’s also hilariously funny, even to this day.

This one had to have been a rite of passage back in the day for many a prepubescent horn-dog boy, given the copious amounts of nudity- but it’s also the rare film of its ilk to feature a fair amount of male nudity as well, which is something a lot of its imitators didn’t go on to emulate, so there’s something to be said for the certain degree of equality in this area. And rest assured, the pervy teenage boys in this flick get their comeuppance in some decidedly unexpected ways, including a scene involving a peep-hole that has to be seen to be believed. (In a word: ouch!) I also like that it’s set in my old stomping grounds of Florida, making it the rare teen comedy set in the South.

Most of the cast is relatively unknown, with a few notable exceptions, including an early turn by future “Sex and the City” Samantha, Kim Cattrall; former football player Alex Karras (“Mongo” in “Blazing Saddles”), and cult film favorite Nancy Parsons (“Motel Hell”), plus the unforgettable Chuck Mitchell, as the titular Porky, a role that so defined him that he went on to be credited as Chuck “Porky” Mitchell in several other films after. Beware the sequels- the second one doesn’t even have Mitchell in it- and stick with the original, which was directed by, of all people, Bob Clark, best-known for the classic “A Christmas Story,” which was made the following year, believe it or not!



Jon Heder gets his hipster chic on in "Napolean Dynamite." Courtesy of

Jon Heder gets his hipster chic on in “Napolean Dynamite.”
Courtesy of

32. Napoleon Dynamite (2004)

One of the quirkiest films on this countdown, the flick was made for all of $300,000 and grossed an astonishing $46 million. Now that’s a solid return investment! The film is a virtual definition of an oddball indie movie- you are either going to love this or hate it with a fiery passion. To me, what makes or breaks the film is your opinion of Napoleon himself, played in a star-making turn by Jon Heder, who got all of $1000 bucks for the job. (Don’t worry, he rightfully re-negotiated his deal and got a cut of the profits later on.)

It’s a nutty, deadpan flick chockfull of quotable lines and mannerisms that were oft-imitated for years to come, which may help to explain why some people hate it so much. Be that as it may, I’m not sure I want to know anyone that didn’t at least smile at Napoleon’s show-stopping dance routine at the end, set to the all-but-forgotten Jamiroquai’s “Canned Heat.” I also got a kick out of his unlikely best friend Pedro (Efren Ramirez, “Eastbound & Down”) and his quest to become class president, which spawned an enormously popular series of t-shirts with the slogan “Pedro for President.”

Husband-and-wife writer/director team Jared and Jerusha Hess went onto to do the equally-divisive cult flicks “Nacho Libre,” with Jack Black, and the underrated “Gentlemen Broncos,” with Sam Rockwell (“Iron Man 2”). The film also features Haylie Duff, Hilary’s sister; Tina Majorino, of “Veronica Mars” fame; and comedy regular Diedrich Bader, of “Arrested Development” and “The Drew Carrey Show.” To be sure, it’s not for all tastes, but if you like your teen comedies a bit left-of-center, this one’s for you.

Rushmore31. Rushmore (1998)

Before Wes Anderson’s name became synonymous with faux-literary films that play like adaptations of books that don’t actually exist, such as “The Royal Tenenbaums” and “The Grand Budapest Hotel,” he made this idiosyncratic teen comedy that’s every bit as eccentric as his later work would be, but in a different, much more accessible way. Co-written with frequent collaborator, actor Owen Wilson, this is the tale of an outcast student at a private high school, Max Fischer (Jason Schwartzman, in his break-out role), who finds an unlikely friend in industrialist Herman Blume (Bill Murray). All is well until they both fall for the same woman, teacher Rosemary Cross (Olivia Williams, “Dollhouse”) and find themselves competing for her affections in hilariously immature fashion.

While I’ll allow that, even at only 18 at the time, Schwartzman seems a bit too old to be playing a 15-year-old, the film is so offbeat and charming that it all but makes up for it. Besides, who doesn’t love Murray? To say the least, this is not your typical teen comedy, and I hesitated to even include it for that very reason, but in the end, I did because, if anything, it certainly nails the awkwardness of being infatuated with someone completely out of your reach, a distinctly teenage experience for those of us who ever fell for an older woman, myself definitely included.

On the other hand, some may rate this even higher, depending on one’s sensibilities. It’s certainly smarter than the average teen movie, that’s for sure, but then, would you expect anything less from Anderson? I can’t say it warrants a higher ranking than this for me personally- the film’s tone was so stylized and distinctive, it had to grow on me, as did Anderson’s future work- but it definitely deserves a place on this list, so here it is.

Well, that about does it for Part One of the list. Be sure to keep an eye out for Parts Two, Three and Four in the weeks to come. Don’t forget to list your own favorites down below!

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About Mark Trammell

Mark Trammell is the resident entertainment critic at UAB, the University of Alabama at Birmingham, where he is also a Graduate Student and does a vid-cast movie review show. He is a life-long fan of films and has a pretty whacked-out, all-over-the-place movie collection that would give most sane people pause. He loves horror movies and Disney flicks and isn't entirely sure there is a difference. He one day hopes to put his money where his mouth is and inflict his own perverse vision on society, entirely so that he can tell people who ask: "If you think you can do better, why don't you make a movie yourself?" to shut up.
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