John Cusack is puffing on a fat cigar. It's incongruous, seeing him dressed all in cool, casual black, sucking on a Cohiba, like a goth who has crashed a Hollywood mogul's house party. "Yeah, maybe we shouldn't mention the cigar," he says. "I don't want people to think I'm this movie cliche. I'm certainly not a mogul – in fact, nothing could be further from the truth."

I don't think there's any danger of Cusack being mistaken for a movie mogul. But the cigar begins to feel somehow appropriate. The more he smokes it, the more at ease he becomes with it, until he owns that damn cigar and waggles it like a spare, stubby finger. And, it seems to me, that's Cusack all over. He's always been the outsider, the one who shouldn't be there yet somehow owns his space and his career.

He's been in more than 60 movies since 1983, from blockbusters such as Con Air and 2012 to genre-bending comedies Being John Malkovich and Grosse Pointe Blank as well as teen classics Sixteen Candles and Say Anything. He has worked with directors including Terrence Malick, Woody Allen, Clint Eastwood, John Sayles and Stephen Frears. But he was also in Serendipity and Must Love Dogs.

"I'm still here, desperately groping in the dark," he says of his career. "Increasingly, I feel it's about just trying to remain relevant enough to do good work. Sometimes I think I'm in control, but more and more I realise that it's just a complete farce. It's true, it used to be that if you did a big, big movie then you could leverage it and make some smaller, cooler ones, and I got away with that for a few years. But now, they just want you to put on tights – if you don't put on the tights, they just want to get rid of you. And I'm not putting on the tights, so you know..."

Cusack is 45 years old but seems to have been around for ever, at least for someone of my generation. He's here to talk about Edgar Allan Poe, the author he plays in the silly but entertaining The Raven, in which Poe turns sleuth to figure out why a serial killer is re-enacting the gruesome murders found in his own stories. It's part Saw, part Sherlock Holmes, part ridiculous romp.

"I don't mind you find the film funny," smiles Cusack. "I guess it's ultimately supposed to be a bit scary, but I admit I personally went for the wit and black humour I've always found in Poe. I don't know if that's what they wanted from me, but..."

Cusack likes to tail off. He'll construct a whirling, circular sentence and then not really finish it, other than to punctuate with a cigar puff. "This Poe is both a figment of my imagination and a version of the icon with the black bow and moustache. I didn't want to do a Halloween mask of Edgar Allan Poe, so I looked at a bunch of pictures and found he was always changing. I know he was admired by Joyce, Baudelaire, Dostoevsky, but I like to see him as the progenitor of Norman Mailer and Hunter Thompson and Capote."

Cusack is always funny, in his own way. Even when he shouldn't be, as when playing a lawyer or a lover. Critic Pauline Kael said he had "question marks in his eyes", and that's true of him on screen. His characters always look as if they'd rather be somewhere else but they shrug and deal with whatever situation they're in and move on to something else. Unlike, say, Nicolas Cage characters, who only exist within the confines of their particular movie, I always think of Cusack's creations walking out of the screen and carrying on their story elsewhere, as if exiting a portal. The end of the movie is not the end of that character.

He has often played men struggling with taking the next step. Just as Say Anything was one of the most thoughtful of the John Hughes-style 80s teen movies, Grosse Pointe Blank was by far the best of a spate of 90s high-school reunion films, with Cusack playing a hit man on the cusp of 30, returning to his alma mater. In High Fidelity, he embodied the emotionally stunted man approaching his 40s. "My characters often know it's wrong but do it anyway," he says.

I'm not so sure. I think they're stuck in a mess of their own making but secretly enjoy the pain.

"Well, any time you do anything good, it's man versus himself, right? That's the art, the challenge. You're always confronting mortality and what it means to be human – whether you're 29 and dealing with 30, or you're nearing 40, the existential crisis is never far away… Maybe I'm the go-to guy for that, which is cool. That's where the juicy drama is. Sometimes, though, I just feel like doing Beckett – figuring out what are we doing on this rock, spinning around..."

He's played writers and artists quite often, too. He's been an idealistic playwright in Bullets Over Broadway, a puppeteer in Being John Malkovich, an art dealer in Max. "I had a run of getting those kind of roles. Call it karma, good fortune, whatever. I don't know if I sought them out or they found me. Maybe the universe does want to bring you to certain places for certain reasons – in which case, I don't know what's going on right now because lately I've been doing stuff that has involved me going into the underworld, and I don't know why. There was Poe, then I did The Paperboy with Nicole Kidman, and then a serial killer film called The Frozen Ground with Nic Cage."

I notice that Cusack is reading Peter Ackroyd's biography, Poe: A Life Cut Short, and he shows me the scribblings he's made inside. "I've read Ackroyd on Dickens and on London, too," he says. "I like how he isn't always a slave to historical truth – at least I hope that's the idea. It's kind of what we do as actors and film-makers, inhabit a space between. It's a psychic space, a state of spirit that is deeply part of the human condition and it's a place Poe inhabited, a mix of high literature and pure pulp ... it's rather awe-inspiring."

Cusack still looks young. His hairstyle has hardly changed in years and he looks like his characters on screen. He isn't one for disguises and makeup. Maybe a pair of dark glasses, here, a goatee beard there, but nothing ever gets in the way of what his Say Anything co-star John Mahoney once called "his essential Cusackness". But what will he do when he gets older, I ask, sounding like a financial adviser.

"Ha, well, that's funny because, you know, there is no Hollywood any more – there's just a bunch of banks," he says. "Cinema is in a weird place. It's just different streams of money coming in and different ways to distribute it.

"Hollywood is just a bunch of people going around in Learjets to other people asking them if they've got any money? Well, they might have if they didn't spend it all on jets."

I remind him that Woody Allen said showbusiness wasn't just dog eat dog, it was worse – it was dog doesn't return another dog's phone calls. Our interview coincides with the news that Allen is in fact making a stage version of Bullets Over Broadway, the film in which Cusack did the "Woody role" of David Shayne, the idealistic writer passing off a gangster's words as his own. "Talking of dogs not returning other dog's calls, I haven't heard anything from Woody about Bullets on stage, so there you go," he grins.

However, I venture, that might be a blessing. These days he might be offered the Jim Broadbent part of Warner Purcell, the actor who's a compulsive eater. "You know it may happen, my God," and he looks slightly appalled. "I better start thinking about it, but I tend not to look back or forward really, which may be a mistake."

Still, I ask him to rewind a little, if only because it throws a reflective light on many of us, too. American films such as Sixteen Candles, The Sure Thing and Say Anything were staples of my own, less glamorous British suburban youth. Cusack was always different from the rest of the Brat Pack and while their careers have had highs and lows, it's as if he has always been playing versions of those 80s characters. He creates real people who last the distance.

"I was 16 years old," he says of the 80s. "I don't remember much. I got a couple of roles by being in the right place at the right time in that I was a teenage actor who had some chops and some training and there was a vogue for movies about kids. And then I parlayed that into a lead in a Rob Reiner movie [The Sure Thing] and suddenly I was doing leads."

Director Stephen Frears cast him as Roy Dillon in 1990's The Grifters, my favourite Cusack performance. "He was really relieved I hadn't seen any of what he called his 'teen films'," recalls Frears. "But actually, it was clear to me he was just a very good actor. In truth, it was between him and Robert Downey as to who would get the part and I just had a feeling for John."

Frears also remembers that, despite his obvious talent, Cusack was still very young. "He was good by about 5pm, so I shot all his scenes around then. Mornings, he was hopeless. John's dad once told me it was a relief for their family because John had left for Hollywood aged 16 and had got to behave like a teenager in films instead of being moody all around the house."

Cusack and Frears remained friends and it was the actor who called the director a decade later to persuade him to read a script he'd adapted from a British book, High Fidelity. "I'd read the Nick Hornby novel and thought there was no way it would make a film, especially as they now wanted to do it in Chicago," says Frears. "But John had really worked out how to get into the book's interior monologues and it was all rather brilliant. As soon as we began work, I realised how much he'd grown up in the 10 years since The Grifters and was able to take responsibility for that film."

For Cusack, The Grifters took him away from teen idol status into something more serious, drawn as he was to the darker world of Jim Thompson's novel. It took him out of the Hollywood glare. "But I was never a joiner," he tells me. "I tried – I had people I admired and liked and wanted to hang with, but I ended up starting a theatre company and that took me back to Chicago... I guess I wasn't a scenester in the end. Something must have worked out right as I'm still here – but I'm only a binge socialite. I'll be out in the world for a couple of months, but then I disappear. If I look back and think about whether I'd have done anything different, I would try and be more networky as some people got very successful that way."

It's odd. To me, Cusack is a great success with some terrific films to his name, yet he's never had an Oscar nomination – even his sister, the fine comic actress Joan, has had two. Cusack looks like he doesn't care too much, on screen at least, yet one gets the feeling he thinks he could and should do more. Unlike, say, Robert Downey Jr, another fast-talking star who rose to fame in the 80s, Cusack hasn't got a superhero or detective franchise to keep him going.

In a way, Poe could have been his Holmes, except The Raven rather precludes a sequel and "nevermore" is, after all, the titular poem's famous refrain. "I've loved playing Poe and it's a lot of fun," he says. "We could do prequels if it all works out but I kind of like the darker, more absurdist stuff of his, stories like "The Imp of the Perverse", and it's simply not the stuff of big movies."

If he weren't so tall (6ft 3in), I say, imp of the perverse would be a good label for him. His eyes sparkle with delight. "Oh I like that," he says. "I don't know how perverse I am, but I can try." And there's just time for another suck on that cigar before it goes out.

The Raven is out now