John Cusack and Generation X

A top five list in honor of the King of (Un)Cool

I used to have a saying: “Anything starring John Cusack is cool.” I meant it. Coming in on the tail end of Generation X placed me about 11 years behind the man. He was often the misplaced geek who gets the girl; I was a geek eleven years his junior who could only dream of getting the girl. John Cusack was to so many of us, a god.

It’s easy to understand. During the 80s, Cusack was an awkwardly handsome guy. He didn’t have soap opera looks, but he had enough. What put him over the top was a sense of internal sweetness coupled with quick wits and a few loyal friends. We nerds believed it when John Cusack got an out of his league Ione Skye because it meant that we too had the possibility of attracting our own version of Ione Skye.¹ Cusack was for a time, not only a god, but even more than that—he was Generation X on film.

Kate Jewell and I talked about our reverence for Cusack during this week’s podcast, which talked about his movie High Fidelity in context with her new book about the history of college radio. Kate and I are both Xennials, meaning that we’ve both struggled finding our place amongst Gen X or the Millennials. We weren’t cool enough for one and felt way too old for the other. Perhaps we are the middle children of our era, with Cusack, Ally Sheedy, Rob Lowe, Molly Ringwald, Matthew Broderick, and a few others being the elder siblings we idolized and whose lives we never quite lived up to.

Cusack has maintained a long career in Hollywood. Yes, he is most notable for work he did in his late teens and early 20s, but that I don’t think we should discount that he’s been a working actor for forty years. Most careers doing anything don’t last that long, let alone a profession that demands “hot” and “new.” So in honor of this week’s pod, I’ve decided to list my Top Five John Cusack performances, in descending order.

Gross Pointe Blank (1997)- In 1997 John Cusack was beginning a resurgence in Hollywood, starring in this film along with Con Air and voicing the role of Dmitri in Anastasia. He’d follow in the immediate years afterwards with films like Midnight in the Garden in Good and Evil, The Thin Red Line, and Pushing Tin (criminally underrated). In some ways, this film served as a parallel to his own career. After making it big in films about high school, Cusack performed as supporting actor in a number of films, but none of those being his films. Gross Pointe Blank saw Cusack’s assassin literally returning to high school for his reunion, battling an odd Dan Akroyd and wooing Minnie Driver. The film marked a return to form for Cusack but maybe stated something else—in 1997 a good portion of the demographic was in it 30s. Generation X were now adults.

High Fidelity (2000)- The film is often associated with GPB, so much that I remember buying one of those combo DVDs with both films on the same disc. High Fidelity is an interesting role for Cusack. One of his great strengths as an actor is just how likeable he is. It’s perhaps a weakness at times too, because it’s hard to buy him in the rare villain roles he’s portrayed. I’m sorry John, we just want to root for you. And that’s what makes this movie such a gem. Cusack’s Rob Gordon is almost entirely unlikeable throughout the entire film—he’s arrogant, self absorbed, oblivious to the damage he inflicts on others—and yet we watch anyway. We do get a character arc out of his record store owner, which is perhaps a testament to Cusack. I’m not sure many other actors would carry us through the film without throwing the television out the window first. A really strong supporting cast and a phenomenal soundtrack really complement his performance.

Hot Tub Time Machine (2010)- We all have comfort movies, the kind we watch when we are fighting off the flu on our couch and can manipulate only the remote control. This is mine. Once again Cusack returns to his high school days, this time literally, courtest of the eponymous wormhole device. HTTM sounds ludicrous, but it’s a brilliant take on memory, masculinity, friendship, lost loves, and the 80s all filtered through our own relationships with Cusack and his films. Some of the jokes are vile and sophomoric, but that’s the point. We are laughing at these dudes, and to an extent, our younger selves. (Roger Ebert gave it three stars while wondering if it had pushed the vocabulatory limits of the f-word.) As with the other films on this list, the supporting cast buoys Cusack’s performance, including a pre-Marvel Sebastian Stan and Rob Corddry having more fun than any human on a movie set ever. As a guy who has often lamented missed opportunities and the chance to do things over again, this film hits home. Of all the films on this list, this is my favorite and it’s not close. Hot Tub Time Machine is one of my favorite films ever.

Better Off Dead (1985)- So it’s down to the final two and yes, it’s the final two you were expecting and for good reason. I debated which of these had to be number one, and despite this film being my introduction to John Cusack, it takes the silver. That shouldn’t be a consolation, though. This movie defines geeky cool. Cusack’s freshly-dumped and suicidal Lane Myer can’t seem to do anything right but manages to haplessly attract the attention of Monique, a French foreign exchange student, with whom he eventually falls in love. A hallmark of Cusack films, the movie features quirky supporting characters such as his paperboy-obsessed father. The movie’s climatic ending of a ski competition is directly channeled in Hot Tub Time Machine and for good reason. When I think of Cusack, I think of this movie.

Say Anything (1989)- It had to be this, didn’t it? You can’t have a list of John Cusack performances and not have his single greatest moment at the very top. You were singing Peter Gabriel’s “In Your Eyes” before you even got to this movie. And my guess is that you’ve had your own version of Lloyd Dobler underneath Diane Court’s window sometime in your life. Ione Skye is fabulous in this. Her moment with the pen when she breaks up with Lloyd, simultaneously breaking both of their hearts, is one of my favorite moments in film history. As the youngest of Gen X, this film taught me what was ahead—though I’m still waiting for my own boombox moment. And that’s the power of this film. It makes us believe in the Grand Gesture, even when the following decades may have sapped that from us. I believe in Lloyd and Diane to this day. I wonder where they are and what they are doing. But in my mind, they are together.

So what do you think? What did I miss out on? What are your memories and who or what defines the generation for you? Let me know below. And oh Hell, here ya go:

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HATM Podcast

We’ve got a great Christmas podcast coming for you on Wednesday, but if this post has you riled up, you can still here my discussion with Kate Jewell about High Fidelity below.

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HATM Sunday

So this Sunday is Christmas Eve, and even heathens like me take some time off every now and then. So, no film this weekend. Be with yours. We’ll be here afterwards. Because we’re doing HEAT on New Year’s Eve. Finally.

See ya soon.

Jason

1. Note: I never did get Ione Skye.