We Miss the 90s: Clueless


In this regular column, Justin Rozzero and Jen Engle exchange emails reminiscing about the greatest decade in history: the 1990s. Justin & Jen have been friends since 1997 and have been trading emails and instant messages about 90s nostalgia since the day they met. Now, they take it public. If you have suggestions for future topics, please email us at the addresses below!

Justin: Let’s get this party back up and running by delving into the quintessential 90s pop culture movie… Clueless! If I had to show someone from the future one movie to describe what it was like to be a teenager in the 90s, non angry grunge division, this is it. Could anyone but Alicia Silverstone have pulled this off? It recently came out that she auditioned for My So Called Life but was basically too good-looking for the role. Would she have been better off doing the show instead of Clueless?

Paul Rudd! Brittany Murphy! The father that is in a ton of 90s stuff! Stacy Dash! Donald Faison! Jeremy Sisto! Breckin Meyer! All star 90s cast… Who is your favorite character?


Jen: Excellent choice, Justin! This is one of my all time favorite movies and such a great representation of the 90s! I probably quote this movie at least once or twice a week.

I don’t think anyone else could have carried the movie quite the way Alicia Silverstone did (not to mention the fact that Clair Danes IS and ALWAYS will be Angela Chase. Unless we are referring to her acting on Homeland, of course.) Silverstone not only looked the part but she really came across as a Valley Girl. So, no. I think this was all fate and she and Claire Danes followed the right path.

I remember going to see this at the movie theater and it was packed to the walls with high schoolers. I was a sophomore and I wanted Cher’s life. Favorite character was obviously Cher. I still want her closet and wardrobe.

Who is your favorite out of the cast? Did you relate to any of the characters? Do you think Cher’s mom really died of a freak accident during a routine liposuction? What ever happened to Cher’s best blouse from Fred Segal?


Justin: As if! I agree that Silverstone was the best fit, as she nailed Cher to a tee. It was a fantastic performance.

I did not see this one in the theatre, but have seen it so many damn times since that I practically have it memorized. It is in my rotation of “must watch to the end regardless of when I turn it on” movies. I always enjoyed Faison’s Murray quite a bit, but outside of Cher, Josh was probably my favorite. Paul Rudd was perfect as the rudderless, idealistic college dude of the 90s. It was a trope of many movies at the time, so it wasn’t easy to stand out, but he did.

Not sure I related to any to be honest as Josh would have been the closest but I just wasn’t in his position at the time. I believe the story of the liposuction death, seems very likely and quite sad. The blouse? An eternal mystery.

Which scenes are the most iconic and memorable to you? I have a couple, but want you to share first.

By the way, Dan Hedaya was a force as Mel the Dad. Also, do you think Ms. Geist and Mr. Hall lasted? They seemed meant to be!


Jen: “Can I get a pass I left my Cranberries CD in the quad”. I’m pretty sure I can recite the entire movie. I have the same problem with this movie. If it’s on TV I can’t pass it up, even though I obviously own it on DVD.

Most memorable scenes? So many! When Cher finds Josh in the kitchen and whines about Radiohead playing (because they were one of my favorite bands in high school and still are), when Cher is teaching Tai life lessons. When Tai almost dies at the mall. When Cher tries to seduce Christian and he complains about his “ulcer”. When Christian shows up in his bright yellow car and blasts Billie Holiday and you just know she stands no chance. When Cher realizes she likes Josh. When Josh realizes he likes Cher. And of course, the pivotal scene of when that girl’s shoe smacks Tai in the head at Travis’ party and knocks her out.

Dan Hedaya was scary, he played the litigator/dad so well, I was afraid of him in the audience. I couldn’t believe Cher would tell him what to do. Ms. Geist and Mr. Hall are happily married with 4 kids right now. Did they last? Of course they did. What a silly question!

Justin: That is a great list of scenes and really hammers home just how iconic the movie is. And you didn’t even mention the driving lesson or the head shaving scene. Trivia time…

What was the name of the town that Cher holds the charity relief fund for?

Did you think it was a bit weird that Cher and Josh were step brother and sister and then hook up? Deep down that always bugged me just a tad…

If you had to pick three other 90s movies to put in a time capsule with Clueless to fully explain the 90s, which would you choose?

clueless-600x337Jen: That’s because I’m keepin’ it real! Don’t call my mom!Pismo Beach. Cher was Captain of the Pismo Beach Disaster Relief. Some people lost everything, Justin. They need skis, caviar and uh, ‘glassware’. It was a little weird to have step brother and sister hook up, but as Cher said their parents were barely married and they weren’t related by blood. Personally, I wouldn’t go there but hey, it’s Hollywood and it worked for the story

Ohhh good question! I would choose She’s All That, Empire Records and 10 Things I Hate about You. Each of these movies had a pretty great cast that for the most part went on to do a lot of great things.


She’s All That was a fun story and they made you feel for the underdog, Laney. You can’t describe the 90s without Freddie Prinze Jr. How Matthew Lillard wasn’t in all of my choices, including Clueless, I don’t know. Wouldn’t he have made a great sidekick for Elton? And as a side note, Matthew Lillard is great in The Bridge on FX. Not his normal goofy self and you get to see his dramatic side.

Empire Records is one of my all time favorite movies. The soundtrack is great and I always felt like those characters were like the group of kids I hung out with. We were all really into music and I spent so many hours lost in the racks at Newbury Comics, it’s a wonder I never worked there. It was a great movie for Liv Tyler, she was just breaking out after starring in like every Aerosmith video in the 90s.

10 Things I Hate About You had a great cast of (actually) geeky actors and the popular kids. Loved Joseph Gordon-Levitt in that film (and still do. Have you seen (500) Days of Summer? No?!!! Finish reading this and then go watch it). It’s one of my favorite Heath Ledger movies, I always loved his comedic roles.

What would you choose? I had a tough time deciding between Empire Records and Romeo + Juliet. R + J is one of my favorites but I thought Empire Records represented the alternative music genre from the mid 90s so well. Ah. I still can’t decide if I made the right choice. Okay, I am adding a 4th. Romeo and Juliet represent!

Justin: Pismo Beach for the win! Lots of great choices there. I will make a case for Mallrats. We have to have at least one Kevin Smith film in there, just due to the sheer volume of 90s actors and actresses that were always in his movies and Mallrats was just the most 90s. Hanging out at the mall is still a thing but in the 90s it was THE thing and this one captures that whole culture perfectly.


How about Free Willy? No? OK.

I feel like American Pie could be in here too as it captured high school to a tee and features tons of 90s music and burgeoning technology, such as Jim using a webcam and sending out the link via email. Plus, he relied on hard copies of his adult entertainment and not the web. It captures what the end of the decade was like as the new millennium dawned. I wouldn’t go to war to include it but I think it has to be in the conversation.

My only other gripe would be to include Can’t Hardly Wait over She’s All That. The party and Seth Green’s character alone make that whole thing so uber 90s.

OK, any final thoughts on Clueless? What made it so damn good? Will you show your hypothetical children this movie someday and say THIS is what the 90s were like?

Jen: I have to agree with Mallrats. I’m not really sure why I didn’t include it, but I love all of Kevin Smith’s movies. It even had one of those 3D pictures in it! It was a boat! I could never see those images. Sigh.

Um, no. No Free Willy.


I kept American Pie out of it because it came out in 1999 and the more I thought about it, the more it seemed like a movie for the 2000s. Can’t Hardly Wait was a great one too…Seriously, we should have made this a top ten list. Now I have a long list of movies I need to watch again.

Clueless was great for so many reasons. Amy Heckerling adapted a modern-day story from Emma by Jane Austen. She understood the teens of the 90s and the comedic timing was great. Although the director wasn’t our age, the story felt like it was written by someone who was experiencing the things that we were at the time and by not someone who pretended they were. The fashion, the slang, the music, the issues they dealt with. She made the girls watching want to be Cher, and the guys watching wish they were Josh. I can’t really explain it, but it was released 18 years ago (Yes, Clueless is an adult!) and it still draws me in.

My hypothetical children will be awesome, so obviously they will watch this movie. They will find it for themselves, I won’t even need to show them the way..

Justin: And with that we will wrap up another installment. You are up next, so make it a good one! Up to you if you want to choose Ren & Stimpy. They are way existential after all!

Be sure to check out the full We Miss the 90s archive!