Best: Grosse Pointe Blank (1997)
Counting Tarantino amongst its devoted fanbase, this defining ‘90s dramedy gave Cusack one of his most iconic roles – as the titular Blank, an assassin whose high school reunion coincides with the killer’s sudden questioning of his current profession.
Head-spinning dialogue, an awesome soundtrack, and killer casting mark this one out as a Cusack Must-See. Seriously, if you don’t watch anything else on this list, indulge in Grosse Pointe Blank (assuming you haven’t already). Read more about it here .
Worst: War, Inc. (2008)
A triple threat, as Cusack acts, writes and produces this spiritual sequel to Grosse Pointe Blank that attempts a similar quick-witted satire, but fails almost entirely to capture the same jovial fun.
Cusack is an assassin who is battling his own demons as he is tasked with killing an oil minister. What begins as a well-intentioned farce that takes a dig at the military industry quickly falls apart as its absurdities pile up.
“The people who seem to like the movie think there is more than one kind of way you can laugh,” says Cusack. “Some say, ‘That’s not funny.’ Well, it’s not really meant to be funny. It’s meant to make you laugh, but to make you laugh because you’d rather not cry.” Um, okaaaaaay.
Best: Sixteen Candles (1984)
The ‘80s – terrible clothes, awesome music. If girly pop’s your thing, of course. Cusack teams up with his namesake John Hughes for a thoughtful teen comedy that goes against the grain of the raunchy teen romps of the era, and wound up re-defining the genre it sprung from.
This was just Cusack’s second film. He and sister Joan Cusack were selected to appear by Hughes after he spotted them on a Chicago street. Luck be a lady! The sibs would go on to appear together in a further eight movies (having already tangoed in Class ).
Worst: Americas Sweethearts (2001)
“Acting can be pretty challenging,” Cusack says. “I can't say making a romantic comedy is challenging, but to do anything well, you have to put yourself into it. But no, if I'm doing some commercial movie just to keep my name in the public eye, then it's just a job. You don't have to sweat it too hard.”
Uh, yeah it shows. Obviously treading water in comfy, glossy fare, Cusack’s appearance in America’s Sweethearts is a particularly nauseating blemish on his CV.
Best: Hot Tub Time Machine (2010)
The King of the ‘80s returns to the era that made him – and in an oh-so-funny twist, his character absolutely hates the ‘80s! Daft in all the right ways.
Most impressively, the producers managed to find a young Cusack looky-likey (Jake Rose) who made us double take and really believe we were back in the ‘80s. Good stuff.
Worst: 2012 (2009)
Oh, John. We’re sure that Roland Emmerich is very charming, what with his gargantuan budget and promises that absolutely zero brain power was required during filming.
But 2012 is Emmerich bottoming out. Tracing over the blueprint of former apocalyptic actioners like his very own Independence Day and The Day After Tomorrow , 2012 is paint-by-numbers end-of-the-world rubbish. Still, Cusack looks like he’s having a bit of fun.
"It was fun. It was nice to get offered the movie," says Cusack. "It's a big popcorn movie and so some of it is fantastic and surreal, but mostly he was just sort of an average person trying to survive." Like us watching this.
Best: Stand By Me (1986)
Beloved coming-of-ager in which four young boys go on a journey of self discovery as they seek out the body of a dead teen.
Cusack crops up in flashbacks as the dead brother of a mourning Gordie (Will Wheaton), just one of the fantastic performances that buoy this adaptation of Stephen King’s novella into the territory of bona fide classic.
We challenge you not to weep. Or develop a sudden phobia of leeches.
Worst: Igor (2008)
Ah, celebrities lending their voices to moving pictures - ain't it grand? With many slebs diving at the chance to do minimum work (stand in a booth for five days) with maximum pay out (money, money, money!), it's a process that's the epitome of phoning it in. They don't even have to get dressed if they don't want to.
Sadly, Cusack's go at the formula resulted in the disappointingly unfunny Igor . Cusack voices the titular monstrosity, a hunchbacked assistant to a scientist who dreams of becoming a scientist himself.
It’s difficult to tell exactly who Igor was made for, with its random cultural references seemingly skewed by a nervous studio. Disappointing.
Best: Say Anything... (1989)
Fan favourite teen comedy, in which Cusack plays Lloyd Dobler (a role he beat Christian Slater to), a sharp, charismatic outsider. He makes eyes at Diane, an over-achieving lovely. They fall for each other, fall out, then attempt to work through their issues.
During that infamous boom box serenade scene, Cusack was playing his favourite Fishbone tape, not Peter Gabriel’s ‘In Your Eyes’ as in the final cut.
“I'm aware of the affection those characters inspired,” says Cusack. “I feel close to Lloyd in Say Anything.. . He was like a super-interesting version of me. Only I'm not as good as him. Whatever part of me is romantic and optimistic, I reached into that to play Lloyd. Of course, now it's all gone. Now I'm just bitter.”
Worst: Serendipity (2001)
“I've made 10 good films,” Cusack acknowledges. “The ones that suck I tend to blank out. It's like I never even made them. Well, there aren't 40 that are great, put it that way. But that's fine. Ten is a good batting average.”
Ask him about Serendipity and Cusack will probably “blank”, then. It’s a piece of forgettable film lint, made the same year as America’s Sweethearts (must’ve been something in the water in 2001) and equally as heave-inducingly soppy.
Best: Being John Malkovich (1999)
Cusack and Cameron Diaz as you’ve never seen them before – and never will again.
“I like to take risks. With acting, you wanna see if you can get into trouble without knowing how you're gonna get out of it,” the actor says. “It's like the exact opposite of war, where you need an exit strategy. When you're acting, you should get all the way into trouble with no exit strategy, and have the cameras rolling.”
They don’t come any riskier than Being John Malkovich , an outrageous mind trip that features Cusack as a puppeteer, Diaz his frizzy-haired wife. Unforgettable.
Worst: Class (1983)
A stumbling entry into the world of movies, as Cusack makes his debut alongside fellow bratpackers Andrew McCarthy and Rob Lowe. The contrived plotting sees a private school brat falling for an older woman who turns out to be his roommate’s mother.
Melodramatic but often insanely boring, Class is the ‘80s teen comedy in prototype form, with all three actors going on to greater things. Watch The Graduate instead.
Best: High Fidelity (2000)
“I never wanted to come off as self-important,” says Cusack. “If I did, then I suck. But these days, I certainly make fun of myself a lot more. I’m willing to open up the yearbook and let go.”
This time around, the actor’s triple threat of actor, writer, producer worked, as Cusack adapts Nick Hornby’s 1995 novel into a slice of cinematic genius. As list-obsessed Rob Gordon, Cusack excels at transforming a stubborn character into a human being.
Worst: Must Love Dogs (2005)
Turd alert! You can get fined a lot of money for leaving your dog’s little gifts in parks. We think people should get fined for leaving bits of filmic excrement like this lying around Hollywood.
Oh fine it’s not really all that bad, but Must Love Dogs is as predictable as they come, despite Cusack’s strong turn against Diane Lane. Best leave this one in the pound.
Best: The Sure Thing (1985)
An ‘80s spin on It Happened One Night , with Cusack and Daphne Zuniga taking on the roles originally played by Clark Gable and Claudette Colbert.
“I remember the '80s being about the Cold War and Reagan and the homeless problem and AIDS,” Cusack says now. “To me, it was kind of a dark, depressing time.”
But you wouldn’t be able to tell from this bright, breezy offering. Cusack and Zuniga aren’t always given enough material to work with, but Sure Thing remains sweet and fluffy.
Worst: The Ice Harvest (2005)
Another comedy misfire for Cusack. This attempt at neo noir falls flat despite its high profile contributors – from its stellar cast and Oscar-winning scriptwriter to director Harold Ramis.
Cusack’s favourite film noirs? “ The Killers I thought was great. I think Asphalt Jungle . What else? Double Indemnity . Chinatown , right? You could go on. There are so many great ones.”
Sadly, this isn’t one of them.
Best: Max (2002)
The same year that he briefly appeared as himself in the brilliant Adaptation , Cusack played the titular Max Rothman, a one-armed, celebrated art gallery owner who befriends aspiring young artist Adolf Hitler (Noah Taylor). Despite Max's help, Hitler decides to forego his art, instead immersing himself in politics.
“I think a lot of films have oversimplified this kind of power-hungry demonic monster,” says Cusack of previous Hitler incarnations, “which is certainly true. This kind of talks about some of the other things. The nature of the film addresses the question. The nature of the film is to examine it and not oversimplify his motives.”
Great performance, great film.
Worst: Martian Child (2007)
“ Martian Child was just a movie the studio [ New Line Cinema ] offered me and it was the best job I could get at the time,” Cusack acquiesces. “It was about a relationship between a guy and another kid, and I thought that was good. It was a sweet movie. They offered it to me and that was the extent of that.”
Wow, we can feel the passion alive and well there, Johnny Boy. Overshadowed by corporate advertising (M&M’s and Lucky Charms are the real stars here), Cusack is the only dimly charming thing in this manipulative misfire.
Best: 1408 (2007)
No, not the prequel to 2012 .
This is a creepy Stephen King bone-chiller, and one of the better entries in King’s novel-to-movie oeuvre. Cusack plays paranormal debunker Mike Enslin, who checks into room 1408 in the Dolphin Hotel, which is said to be haunted.
Bucking the trend for torture porn, 1408 skimps on the gore, going instead for the untapped vein of psychological horror. As Cusack begins to lose his grip on sanity, the flick enters genuinely disturbing terrain.