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Six Definitive Films: The ultimate beginner's guide to John Cusack

Enjoying a significant amount of success through the 1980s and 1990s, American actor John Cusack remains an icon of Hollywood, despite having fallen out of favour with the industry in recent years. Known for his iconic performances in such films as 1989’s Say Anything… and 1997’s Grosse Point Blank, for a short period of time there were few actors that could match his charisma and on-screen presence. 

Not as popular as he once was, Cusack criticised Hollywood back in 2014, saying of the industry, “The culture just eats young actors up and spits them out. It’s a hard thing to survive without finding safe harbour…It’s a whorehouse and people go mad”. This was illustrated in the David Cronenberg film of the same year, Maps to the Stars, which explored the true insanity of modern fame and media attention.

Having worked with the likes of John Hughes, Rob Reiner, Cameron Crowe, Stephen Frears, Robert Altman, Terrence Malick and Spike Jonze, Cusack has enjoyed a healthy career that spans big-budget ventures and small independent flicks. From his debut in 1983 to his most recent movie, let’s take a look back and assess the six most definitive films of John Cusack’s career. 

John Cusack’s six definitive films:

Sixteen Candles (John Hughes, 1984)

Taking a supporting role in Class one year prior, it was the release of Sixteen Candles in 1984 that would properly introduce Cusack to contemporary audiences, starring in one of the lead roles of John Hughes’ celebrated – and undoubtedly dated – coming-of-age romp. Playing Bryce, the friend of the protagonist named Geek (Anthony Michael Hall) in this boy-meets-girl tale, Cusack’s character doesn’t have a ton of screen time, though the film would be integral to Cusack’s development in the industry. 

Two years after Hughes’ classic, Cusack would appear in the Stephen King adaptation Stand by Me, by Rob Reiner, followed by John Sayles’ Eight Men Out and much more to come. 

Say Anything… (Cameron Crowe, 1989)

Cusack’s most iconic role came relatively early in his career, a time when he was still establishing himself as a young star trying to gain a foothold in Hollywood. Collaborating with Cameron Crowe in 1989, the actor starred in another coming-of-age movie that gripped the western zeitgeist, Say Anything, co-starring the likes of Ione Skye, Jeremy Piven, Lili Taylor and John Mahoney. 

Playing a charming young man who falls in love with the highest achiever in high school, Cusack’s role is well-known for the moment in which he stands outside his lover’s bedroom window, holding a stereo high above his head.

Grosse Pointe Blank (George Armitage, 1997)

Logic would suggest that Cusack’s trajectory was headed for significant industry success, though this never truly came to fruition for the actor, who stumbled through the 1990s with a number of forgettable roles. Though he helped elevate Robert Altman’s The Player in 1992, it wasn’t until Cusack took on another romantic role in 1997 that he would once again see success, also helping to write the acclaimed drama, Grosse Pointe Blank. 

Unable to escape the high-school drama, Cusack plays a professional assassin who is encouraged, by coincidence, to attend his ten-year high school reunion whilst trying to find his target. A charming action-comedy, this 1997 flick is too often forgotten from the finest films of the decade. 

Being John Malkovich (Spike Jonze, 1999)

Grosse Pointe Blank was successful in sparking a career resurgence for John Cusack, leading him to further acclaimed roles in Con-Air in 1997, The Thin Red Line in 1998 and Spike Jonze’s Being John Malkovich in 1999. An independent movie and cult sensation, Jonze’s 1999 film stars Cusack as a puppeteer who discovers a portal that leads literally into the head of the real-life actor, John Malkovich.

Taking the lead role in the movie, Cusack commands the camera and fuels this mysterious comedy with a great deal of emotion and well-placed levity.

High Fidelity (Stephen Frears, 2000)

Once again co-writing the screenplay, Cusack’s adaptation of Nick Hornby’s novel of the same name, came just one year after the success of Being John Malkovich, hoisting Cusack into a good industry position come the turn of the new millennium. Returning back to his roots, Cusack plays the leading role in a stylish romantic comedy that follows a record store owner who sets out to recount his top five breakups, including the one in progress.

With a supporting cast that includes Jack Black, Iben Hjejle and Tim Robbins, the film went on to become a significant success and is still considered one of the best music movies of all time. 

Maps to the Stars (David Cronenberg, 2014)

Cusack’s modern career in cinema has been somewhat tumultuous, with many of his projects either failing to chime with modern audiences or simply going straight to video. Arguably, it is the actor himself who worked his way into such a position, failing to challenge himself in the modern industry, instead, relying on such noughties movies as Identity in 2003, 1408 in 2007 and The Raven in 2012. 

In fact, his major role in the David Cronenberg oddity, Maps to the Stars, remains his greatest modern role to date, with the actor playing a father and psychologist trying to hold his family together in the midst of modern fame. Appearing alongside such greats as Julianne Moore, Mia Wasikowska and Robert Pattinson, Cusack fades a little into the background, though still shows to hold his own. 

Perhaps it is this inability to grasp a variety of Hollywood projects that held the actor back from true Hollywood success, sticking to the romantic stories he knows best instead of diversifying his craft. Continuing to work on the lowest rung of the industry, let’s hope Cusack finds his way back to the top of his game, he certainly holds the potential to.