This, perhaps the greatest romcom ever conceived with the male viewer in mind, sees puppy-eyed Cusack reinvented as a hard-edged hitman healed by his love for Minnie Driver – exactly the kind of guy my adolescent self couldn’t help but aspire to

I was too young to connect to the brimmingly sensitive John Cusack an entire generation fell for: I was but seven at the time of 1985’s The Sure Thing, and 11 when Lloyd Dobler raised his boombox to Ione Skye in 1989’s Say Anything. The Cusack I tuned into was the slightly bruised figure visible by the end of the century: the lovelorn Rob of 2000’s High Fidelity, a film engineered so as to rhyme with any boyish pop-lover’s romantic ups-and-downs; before that, the hitman of 1997’s Grosse Pointe Blank, which may stand as the greatest romantic comedy ever conceived with the male viewer in mind, in that it features one character being bloodily skewered with a Biro, and another with a job sourcing mildly obscure 80s vinyl.

There’s a scene two-thirds of the way through the latter film that gets me every time – an unexpectedly tender interlude between the bloodletting and sharp-edged social satire. Our ambiguous hero, the self-improving assassin Martin Q. Blank (Cusack), has retreated to a balcony overlooking his high-school reunion with DJ Debi Newberry (Minnie Driver), the sweetheart he abandoned on prom night. To the sound of Pete Townshend’s Let My Love Open The Door, the pair begin to pick over some unfinished personal business.

“I think I was overly harsh when I said you were broken,” offers Debi, by way of conciliation. “I don’t think you’re broken. I think you’re mildly sprained. Nothing that can’t be mended.”

“Sorry if I fucked up your life,” Martin ventures, perhaps sensing how that “if” might be superfluous.

“It’s not over yet.”

In a film that posits contract killing as a metaphor for the damage we can wreak whenever we get close to someone, the scene works because it opens up the possibility of change and redemption – that a partner might recognise our pain and forgive us all previous trespasses. Grosse Pointe Blank is a peculiarly potent watch for men because the script, written by Cusack with Steve Pink, DV DeVincentis and Tom Jankiewicz, on some level acknowledges all our worst instincts: the desire (often misplaced) to put the world to rights, the anger that can shade over into murderous aggression, the persistent need to do something, anything, with our fists, our dicks, a gun – because that’s what we’ve been hardwired to do.

Blank’s temporary solution has been to isolate himself, first on prom night, now as an “independent contractor”. Note Cusack’s distinctive walk: fast, clipped, guarded, one hand forever poised on the pistol in his pocket. He is, however, more vulnerable than threatening: though he insists his were deserving victims (“You should read the files on some of these fuckers!”), we see the toll this lonely life has taken in the dark rings beneath his eyes, and how he comes alive again circling Debi. Cusack and Driver were a thing once upon a time, and their chemistry remains a joy: not just affectionate and sexy but regenerative, suggestive of all manner of blanks being filled. My inchoate late-adolescent self couldn’t help but aspire to that.

For some while, there was talk of a follow-up – perhaps one in which Martin Blank finds spirituality? But, really, who needs God when you have Debi Newberry? Instead, we got 2008’s War, Inc, a spiritual sequel in which Cusack played a Blankish contractor stalking the Middle East; its Bush-bashing got blunt, and it missed Driver, for all the zip Hilary Duff brought to her role as the Yemeni Britney Spears. There may nevertheless be something equally instructive in the morally compromised figure Cusack now cuts on screen: consider his greasy killer in The Paperboy, The Frozen Ground’s curdled misogynist, or his sweaty, vote-grabbing Nixon in The Butler.

Where earlier Cusack characters displayed a puppy-eyed idealism, here are men tainted by exactly those grim compulsions Grosse Pointe Blank diagnoses. They reflect what might have happened to Martin Blank if he hadn’t met Debi Newberry, and his hurt hadn’t healed; if he’d given into the worst aspects of his nature, and gone more or less entirely to seed.

We don’t all wind up bombing Cambodia or masturbating in front of Nicole Kidman, thankfully, but in Cusack’s recent reinvention as a prolific character actor, there lurks a valuable warning about what can happen to us once the dewy sheen of youth has evaporated.

• Why I’d like to be … Dan Aykroyd in The Blues Brothers

• Why I’d like to be … Scarlett Johansson in Lost in Translation

• Why I’d like to be … Cary Grant in Charade