In the days before rom coms (romantic comedies), there were teen flicks.

Growing up, 1999 was a significant year. It was the very same year that about a tonne of teen flicks were released! One may call it the “teen flick golden era” as it was a teen flick boom, what with the release of more than 10 teen movies in the span of a year. If you know this song and which teen flick it came from, you’re probably on the right track:

“Kiss me out of the bearded barley, nightly, beside the green, green grass. Swing, swing, swing the spinning step, You wear those shoes and I will wear that dress..”


Yes, it’s none other than Sixpence None the Richer’s “Kiss Me”.

1999’s teen flicks were perfect – it was always the talk of the town (between friends), it probably has at least one or more hot then teen star, it’s very befitting for those awkward first dates, it’s likely that it has an awesome original soundtrack, and it’s even fun to watch alone even for guys! And don’t you dare deny it. So, with that being said, here are some of our favourite and most unforgettable teen flicks we’d gladly stay in to watch over hitting the clubs to party any day:

She’s All That

She's All That Movie

Cast: Rachael Leigh Cook, Freddie Prinze Jr., Paul Walker, Matthew Lillard, Anna Paquin, Kieran Culkin, Usher Raymond

“She’s All That” is the story of a popular and hunky high schooler named Zack (played by Freddie Prinze Jr.) who is attempting to date the most unpopular girl in school, Laney (played by Rachael Leigh Cook). Why would he even think of stepping foot in that “unchartered” dorky territory? All part of fun and games, and a jock bet that he made with his buddy Dean (played by Paul Walker). The trick is, Zack needs to successfully turn Laney into an absolute babe before prom but it won’t be easy because she’s quite resilient and other people will conveniently throw wrenches in the work to keep them apart. Of course, all’s well ends well with some super pretty heartfelt moments along the way.

Why we love “She’s All That”? Stellar cast (Usher, what?), great original soundtrack (The Rockafeller Skank, what?), and hot leads. The movie even helped launch the careers of Rachael Leigh Cook and the late Paul Walker! Definitely a must-watch, over and over again.


10 Things I Hate About You

10 Things I Hate About You

Cast: Julia Stiles, Heath Ledger, Joseph Gordon-Levitt, Larisa Oleynik, Andrew Keegan, Gabrielle Union

Oh, Cameron (played by Joseph Gordon-Levitt), you have so many problems! Not only are you a new kid at Padua High School, you have big plans to go after one of the most popular girls in school, the beautiful Bianca (played by Larisa Oleynik). You see, the problem is, Bianca wouldn’t be caught dead dating Cameron because she’d much rather be with the hot model and student, Joey (played by Andrew Keegan). Also because she can’t actually date unless if her sister does, due to her overprotective father. To get to Bianca, Cameron has to first “get to” Bianca’s shrew of a sister, Kat (played by Julia Stiles). So Cameron sets it all up, asking Patrick (played by Heath Ledger) for assistance. As long as Patrick successfully dates Kat, then Bianca will go out with Cameron, right? Oh no wait, there’s still Joey. Gosh!

The most significant part of “10 Things I Hate About You”? The fact that is was based on Shakespeare’s “The Taming of the Shrew”, and that poem, hands down.

Drive Me Crazy

Drive Me Crazy Movie

Cast: Melissa Joan Hart, Adrian Grenier, Stephen Collins, Ali Larter

First of all, oh my goodness Adrian Grenier way before the days of “Devil Wear Prada”! So Nicole (played by Melissa Joan Hart) and Chase (played by Adrian Grenier) are neighbours with one thing in common – they live with their single parents. But that’s the only thing they have in common. Nicole is the popular fashion-loving chick while Chase doesn’t care about the latest fads. Nicole wants a dream date with the star basketball player, but he falls in love with a cheerleader. Meanwhile, Chase’s “non-conformist” girlfriend, Dulcie (played by Ali Larter) dumps him for another man. Now that they have something in common, Nicole and Chase reluctantly date each other to attract the interest and jealousy of their respective romantic prey. Do they end up falling in love with each other?

We really do find it hard to shake off theme song by Britney Spears. Also, protip: Expect a huge parent-related twist when you watch this one!

Cruel Intentions

Cruel Intentions

Cast: Sarah Michelle Gellar, Ryan Phillippe, Reese Witherspoon, Selma Blair

We saved the best for last! “Cruel Intentions” was adapted from the “Dangerous Liaisons” storyline, and perhaps a little bit more R-rated than other teen flicks. Kathryn (played by Sarah Michelle Gellar) and Sebastian (played by Ryan Phillippe) are 2 very wealthy but also very manipulative step-siblings from Manhattan’s upper-crust. In a tale of seduction and betrayal, Kathryn want Sebastian to “deflower” innocent Cecile (played by Selma Blair) because her boyfriend dumped her for Cecile. Sebastian thinks it’s boring and is more interested virgin do-gooder Annette (played by Reese Witherspoon). So Kathryn makes a sexual conquest bet with Sebastian, that he won’t be able to bed Annette. If Kathryn wins, she gets Sebastian’s vintage car, a 1956 Jaguar; if Sebastian wins, Kathryn will have sex with him. It is mentioned that Sebastian keeps a journal detailing his conquests.

For its time, “Cruel Intentions” is super twisted as compared to other teen flicks. We love it!

Which one of the above do you like most? Do you have any suggestions that you’d like us to add to the list? Let us know! Meanwhile, curl up and enjoy a movie marathon of the above teen flicks.



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Eats, sleeps, & breathes music, but drinks mostly coffee & okay, some wine - sometimes, a little too much. A little too obsessed with the number seven, is deathly afraid of horror movies, believes that she writes better than she speaks, & currently feeling a little strange writing a profile about herself.