The Essential John Cusack

In addition to the films that accompanied them, the 1980s produced a lot of memorable characters and actors. Teenagers coming of age and finding their identity were what directors like John Hughes built their careers on. These kids had style. They had pizazz. But most importantly, they all shared tremendous chemistry on-screen. By the time the 90’s came around, some of these actors and actresses lost a measure of fame or found work behind the camera while others stuck around and still nab big roles today. Just look at the famed Brat Pack: Emilio Estevez, Demi Moore, Anthony Michael Hall, Molly Ringwald, and Andrew McCarthy were among the individuals who made a name for themselves and shared the screen opposite each other in classics like Sixteen Candles, The Breakfast Club, Pretty in Pink, St. Elmo’s Fire, the list goes on and on.

John Cusack was also one of those actors who got his start in those films.

Making a name for himself in those famed flicks, Cusack has since gone on to star in numerous films in a variety of genres. Whether it’s horror, romantic comedy, action, independent, drama, there’s very little ground that Cusack hasn’t covered. There’s a certain charisma to the guy that just simply cannot be denied and is just so likeable of a person when you see him. Even in a bad John Cusack film, you always remember his performance.

Which brings me to my next point. Like every performer, not everything John Cusack touched was gold and he’s certainly had his fair share of duds, especially in recent years. I remember he stated as such in an interview he conducted for the Guardian I read a few years on IMDB. Here’s the direct quote:

“I’ve made 10 good films. I’m sure you know which ones they are. The ones that suck I tend to blank out. It’s like I never even made them.”

I think that’s a fair assessment.

In a career that spans four decades, John Cusack has also been apart of some absolute genius work. Here, we take a look at the memorable moments of each decade:

The 1980s
After a small role in Sixteen Candles, Cusack scored one of his first starring roles in the 1985 cult film, Better off Dead. It showcased Cusack’s comedic timing and boyish charm which helped jump start his career early on. In the years that followed, Cusack denounced his involvement with Better Off Dead calling the filming of it one of the worst experiences of his life. What a shame. He went on to contribute a tiny part as River Phoenix’s character’s older brother in Stand by Me in 1986. Cusack finally achieved greatness when he took the forefront in one of my all time favorite films and his finest work in my opinion. That film is 1989’s Say Anything….


Say Anything… was Cameron Crowe’s feature film directorial debut. It tells the story of Lloyd, an underachiever (Cusack) who falls for the immensely intelligent Diane (played by Ione Skye. What the heck ever happened to her?). The acting and storytelling are near perfect. I wish more romance films took notes from something like this. This was undoubtedly Cusack’s breakthrough film which contained the iconic scene of Lloyd holding up a a boombox blasting Peter Gabriel to win Diane’s heart. That scene is etched in the minds of cinema fiends all across the globe.

What you’ll also start to notice a lot in John’s films is that his older sister, Joan, will often co-star with him. They never share equal billing and Joan usually plays a much smaller role in her brother’s films which I find disappointing but funny.

The 1990s
At the turn of the 1990s, Cusack aimed for more mature roles which yielded mixed results. He starred in the Oscar winning Bullets Over Broadway and cult action classic, Con Air, but his finest work of the decade in my opinion was the comedy, Grosse Pointe Blank, in 1997.


Cusack plays a hitman named Marty who tries to win back his high school sweetheart and avoid getting whacked in his final job when he returns home for his high school reunion. The quirkiness of the movie’s content complete with the complexity of Marty’s character helps the film standout in a major way. Are we not supposed to identify with Marty because he kills people for a living and walked out on the woman he loved or are we supposed to feel sorry for him because he wants out of his line of work, is lonely, can’t relate to a lot of people, and desperately tries to win his girlfriend back? While it gets plenty of praise, I still think this is one of the most underrated films of the 90s. In fact, my recent rewatching of Grosse Pointe Blank actually inspired this article.

Cusack closed out the decade with a memorable role as a puppeteer in the adorably strange Spike Jonze film, Being John Malkovich, in 1999.

The 2000s
Cusack’s best film of the 2000s actually dropped right at the beginning of the century with an adaptation of Nick Hornby’s best selling novel, High Fidelity.


Academy award winning director, Stephen Frears, takes the helm of this project about a record store owner who ponders his previous romantic relationships while spewing his broad knowledge on his favorite subject: music, to anyone that cares to listen. Frears relocated the story from England to Cusack’s hometown of Chicago to give it an American flavor. Cusack gives another endearing performance as a fundamentally knowledgeable but romantically clueless individual. He shows quick wit as Rob the pretentious music lover and will have you seeking every track mentioned or featured here.

The rest of the decade sadly wasn’t anything to write home about. Serendipity (co-starring Kate Beckinsale) was a popular movie and a favorite among some of my friends but I honestly was never high on it. Just a tad bit too corny for my tastes. After a promising 2003 with parts in Identity and Runaway Jury and a promising role in the late Harold Ramis’ 2005 flick, The Ice Harvest, with Billy Bob Thornton in 2005,  Cusack starred in films like the romantic comedy, Must Love Dogs, family film, The Martian Child, and disaster movie 2012. All of which were horrible.

The 2010s
While not a great film by any means, Cusack returned to his 1980s comedy roots with Hot Tub Time Machine co-starring Craig Robinson, Clark Duke, and Rob Corddry with Chevy Chase, Crispin Glover, and Billy Zabka in smaller roles.


It had been years since Cusack starred in a laugh out loud comedy and he chose a good prospect to return to form. Four down on their luck friends return to the same ski resort where they lived their most fond memories years ago only to be sucked into a time warp 25 years in the past after a night of drinking in a hot tub. The premise is absolutely ridiculous but everyone involved made it work. It proved that Cusack still had the comedy bug in him and the film performed well enough at the box office to warrant a sequel. It’s too bad he won’t return for it, though (Adam Scott will reprise Cusack’s role).

In recent years, it appears as if Cusack is trying to land an Oscar by working with the likes of Lee Daniels and David Cronenberg. Will he be successful? Well, he’s certainly talented enough. I hope the right role comes along and he kills it on the silver screen just like he has before. If you haven’t seen any of the films profiled here, go on whatever streaming service you own or the nearest Redbox and watch them! How can you not love this?


Written by Matthew Reine

is a New Yorker with a strong passion for film and television. Also the biggest Keanu Reeves fan you know.

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