Boom Boxes and Big Heart: Nerd Initiative’s John Cusack Valentine

With Valentine’s Day just around the corner, watching romantic comedies full of heart is inevitable. A good number of people may be forced into watching a sappy love story with terrible jokes and timing. Romantic comedies have always evolved over the years, and a lot of that experimentation has been done in the last couple of decades. Yet, one actor has made romantic comedies emotionally accessible in a way some leading men haven’t. 

John Cusack is an actor of many genres, including romantic comedies. He took a grab bag of roles in his early career, from offbeat comedies to poignant dramas and, in the case of a few of the films listed below, a little bit of both. When it comes to rom-coms, John Cusack is the treat that makes some romantic comedies easier to digest. He was never your typical leading man in these movies, which elevates them and endears them to the kids who were not popular.

The Sure Thing (1985)

Rob Reiner’s follow-up to Spinal Tap finds John Cusack as college freshman Walter Gibson, who is unlucky in love and failing English, opposite Daphne Zuniga’s Alison. After Walter makes an unwanted pass at Alison during an attempt to tutor him, he sours their already-strained relationship. Walter’s best friend, Lance (Anthony Edwards), invites him out to the West Coast for a sunny California Christmas to hook up with a girl Lance describes as a “sure thing.” The plans are going well until Walter discovers Alison is taking the same rideshare bound for a similar destination to be with her long-distance boyfriend. Despite their differences and a fair amount of trouble on the road, the two bond and fall in love.

While it may have been a weird jump for Rob Reiner after his misunderstood debut, the film set John Cusack up in his first leading role after being a supporting player in his first few films. As expected, Cusack is still finding the voice of the lovesick and borderline nerdy characters he would often inhabit in this early portion of his career, but a lot of this is established in the film’s ninety minutes. His performance gives hope to the kid who may have all the wrong moves, but is open to growth. 

Better Off Dead (1985)

Lane Meyer (Cusack) is obsessed with Beth, his girlfriend of six months. After bungling his ski team tryout, Beth dumps him for ski team captain, Roy Stalin. Lane decides to kill himself. After a failed suicide attempt, Lane tries to put his life back together with the help of his friend Charles De Mar (Curtis Armstrong) and the concern of his parents (Kim Darby and David Ogden Stiers). Things start to turn around when he meets a French foreign student, Monique, who opens a door to love that had been slammed in Lane’s face at the start of the film.

While that description may sound extremely basic, this movie is anything but that. Better Off Dead was the directorial debut of “Savage” Steve Holland. Filled with surreal, absurdist, and dark humor, this is one of the most insane movies you will see, let alone as a love story. Between persistent paperboys, Japanese drag racers obsessed with Howard Cosell, and Van Halen singing hamburgers, Lane finds love and self-confidence. While the film shares some of the same themes with The Sure Thing, Better Off Dead’s handling of young love expands these sentiments. There are so many threads to follow in this movie; the romance story is nearly camouflaged.

One Crazy Summer (1986)

Hoops McCann (Cusack) spends the summer with some friends (Joel Murray, Bobcat Goldthwait) on Nantucket after graduation. Failing to get a scholarship to college through basketball, he must write and draw a love story to get into the Rhode Island School of Design. Along the way, he runs into a rock singer named Cassandra Eldridge (Demi Moore), who is on the run from a biker gang. Wackiness ensues, and with it, Hoops can illustrate a love story for his college admission, his own.

One Crazy Summer reunited John Cusack with Better Off Dead director Steve Holland and co-star Curtis Armstrong. While the film is a spiritual sequel of sorts to Holland’s debut film, it falls flat in a few places. Better Off Dead was lightning in a bottle, and grounding the film with dark subject matter sets it apart from the rest of these films. Holland doesn’t rehash many of the themes or jokes from his first film, but One Crazy Summer doesn’t have much more to say about love that Better Off Dead hadn’t already said.

Say Anything… (1989)

John Cusack plays the high school graduate Lloyd Dobler, who once had a meal with high school valedictorian Diane Court (Ione Skye) at the mall food court. While he’s unsure if it counts as a date, Lloyd definitely feels a connection. When he decides to invite her to a graduation party, the two hit it off. Diane is hesitant to start any type of romantic relationship with Lloyd before she leaves for school, but he is determined to spend as much time as possible with her despite her father’s objections.

This quintessential teen rom-com leans much more to the rom than the com. Say Anything… is Cameron Crowe’s directorial debut after writing scripts for Fast Times at Ridgemont High and The Wild Life. Here, Crowe tells a small and simple story. Cusack’s performance as Lloyd is much more grounded than his previous roles as a young man in love, giving him one of the most iconic roles of his career. While Cusack’s Lloyd moves the story along, the storyline between Diane and her father, Jim (John Mahoney), has just as much emotional weight. Cusack’s performance is funny, profound, and sweet. If Cusack’s previous roles didn’t move the needle for the archetype found in romantic comedies, his portrayal of Lloyd surely did.

Grosse Pointe Blank (1997)

Professional assassin Martin Blank (John Cusack) returns to his hometown of Grosse Pointe, MI to make amends for a hit he had recently botched, coinciding with the same weekend as his ten-year high school reunion. While trying to atone for his most recent mistake, Martin has the opportunity to fix his biggest mistake: standing up his girlfriend, Debbie (Minnie Driver), on prom night. Martin tries to rekindle the romance he once had with Debbie while dodging the bullets of other assassins bent on setting up a union and a couple of inept federal agents on his trail.

Directed by George Armitage, Grosse Pointe Blank is the underrated gem of this list. Featuring music by Clash lead singer Joe Strummer and music from The English Beat, the Violent Femmes, and the Specials, Grosse Pointe Blank feels like an amalgamation of the roles Cusack had been cast in up to that point. Cusack had stretched his legs in several genres in the time between Say Anything… and Grosse Pointe Blank. While it’s not an exact return to the rom-com genre, there are plenty of moments that make this a great date movie.

High Fidelity (2000)

Rob Gordon (John Cusack) was just dumped by his girlfriend, Laura (Iben Hjejle), after two years. Rob navigates the end of his relationship by retreating to the record store he owns, Championship Vinyl, and making lists of the top five records with his two employees, Barry (Jack Black) and Dick (Todd Louiso). As Rob recounts his top five breakups, he starts to see that he may be the problem, and highlights his fear of commitment. 

Based on Nick Hornby’s novel of the same name, the film adaptation of High Fidelity changes its setting from London, England, to Chicago, IL, and also its main character’s surname from Fleming to Gordon. While most of the book’s story is intact, some of the music and movie references have been changed. Like Fight Club, this movie was big for a lot of people, but misunderstood by many of its fans. While unconventional as a love story, it does bring up many good points on relationships and the horrible ways we try to make them work when the clear answer is to just grow up a bit. This is especially true in a film like High Fidelity that is embraced for its soundtrack and pop culture references over its critique of emotional immaturity.

America’s Sweetheart (2001), Serendipity (2001), and Must Love Dogs (2005)

With rom-coms still in his system, John Cusack’s work in the genre continued through the early to mid-2000s with a trio of films that seem to be par for the genre. Here, Cusack seems to go from romantic outsider to typical studio rom-com lead. Just taking a look at his filmography, it appears that he takes on roles that mostly seem interesting to him. Some of these roles almost seem like outliers in comparison to some of the roles we remember him for.

Despite the smaller details of these movies, including America’s Sweethearts being written by actor Billy Crystal or Must Love Dogs coming from Gary David Goldberg, creator of sitcom classics like Family Ties and Spin City, the gloss of these movies is a bit of a turn-off. They are bland additions to the filmography of an actor who was able to work inside and outside the box and make their performances unique.

Rom-coms in general are a tricky beast, and getting some people to watch them takes a herculean task. Some movies, like a good portion of the ones on the list, have a way of Trojan-horsing the romance on you before you even know it. Cusack’s brand of earnest, slightly chaotic sincerity is what makes these films endure. Paired with the manic and lovesick performances that made John Cusack a fan favorite, these films go down easier than most. If you stick to one of these, I think you’ll survive the ninety minutes.

Check out Forrest’s review of Judd Apatow’s, Mel Brooks: The 99 Year Old Man