by If any actor from the last 40 years of Hollywood history knows the industry’s precipitous highs and dizzying lows better than most, it’s John Cusack.
After breaking out as a teen star with 1989’s Say Anything…, Cusack was indelibly etched in the minds of a generation as a lovelorn guy who would do anything to win the object of his affection, as long as that mostly entailed holding a boombox above his head in a grand romantic gesture.
In the ’90s, as he became one of Hollywood’s most interesting leading men, he added several classics to his resume, including The Grifters, Grosse Pointe Blank, Con Air, and Being John Malkovich. Then, at the turn of the century, he arguably hit the high point of his commercial viability with the romcom triple hit of High Fidelity, America’s Sweethearts, and Serendipity.
After this, things started to get a bit unsteady for Cusack at the box office, primarily when he made anything outside the boundaries of standard Hollywood mainstream entertainment. First there was Max, a troubling drama about the friendship between a Jewish art dealer and his angry young client, an Austrian painter named Adolf Hitler. The film posited the idea of how different the world could have been had Hitler realised his potential as an artist, instead of embracing antisemitism and becoming, y’know, one of the most evil men the world has ever seen. The movie was obviously a tough sell, both critically and commercially, and Cusack took the brunt of that failure.
Over the next six years, he starred in a couple of hits, like Identity and 1408, but also a fair few duds, before he took another big risk with 2008’s War Inc. This action-comedy/political satire hybrid was a real labour of love for the star, who co-wrote and produced the film in addition to starring as a disillusioned hitman tasked with killing the CEO of a West Asian oil company. To Cusack, the film was a “spiritual cousin” to Grosse Pointe Blank, in which he played a hitman attending his high school reunion.
Unfortunately, the similarities stopped there, with War Inc failing to cultivate the audience the 1997 black comedy enjoyed. It was savaged by critics, with Cusack’s co-star Ben Kingsley even generating a Razzie nomination for his performance, and even though it had an extremely high box office take in the cinemas it was released in, it was only ever available in a maximum of 32 theatres across the US. In the end, this lack of a wide release doomed the movie to a dismal take of $1.2million.
In the aftermath of this latest disaster, Cusack claimed that it was all part and parcel of his desire to follow his creative muse, instead of always following what the market dictates. “I just do whatever I’m interested in, whatever challenges and provokes me,” he told Chud in 2008, “I don’t mind risking things, I don’t mind failing. It’s okay to risk and fail and extend yourself and work without a net.”
For Cusack, it was better to risk it for the biscuit than not try at all, because that cowardly approach would only lead to regret, confessing, “I don’t want to look back at this period and go, ‘All I did was make money making romantic comedies”.
At the time, the actor probably thought War Inc would just be chalked up as a noble failure, and he’d go back to making the occasional hit followed by another risky proposition. Sadly, the business of Hollywood changed around him in this period, and the ‘one for you, one for them’ mentality that used to serve A-list stars so well became almost extinct. “Now it’s six for them, with a committee cutting the film who weren’t part of making it, and maybe one for you,” he legitimately grumbled to The Guardian in 2014.
Before War Inc, Cusack had only been a part of one direct-to-video film, but since its release, he has been firmly mired in that schlocky, low-budget territory. He hasn’t starred in a theatrically released hit movie since 2014’s Love & Mercy, unless you count the Chinese productions he’s unexpectedly turned up in, such as 2015’s Dragon Blade and 2025’s Detective Chinatown 1900.
When speaking about the downturn in career prospects in 2020, he admitted, “I haven’t really been hot for a long time”, and it’s hard not to point to War Inc as the moment that rot truly began to set in.
