Once Upon A Time ... In Hollywood there was a man named Damon Herriman

Not long ago, former child actor Damon Herriman could only get auditions for "Mr Nice Guy" roles. Beginning his career with a wholesome stint on The Sullivans in the late 1980s, he made his film debut opposite Ben Mendelsohn in 1990 comedy caper The Big Steal. "I played a nerdy nice guy with glasses and 15 years later I was in [TV series] Love My Way playing a nerdy nice guy with glasses and, for that period, that's pretty much all I could play," he grins. "I would never get auditions for criminals, or psychos, or drug addicts or anything like that."

Wearing a grey T-shirt and a faded brown cap – a far cry from our fashion shoot – Herriman's infectious enthusiasm makes it easy to see why casting agents often pegged him as sweet. Which is amusing, really, when three new releases have Herriman rivalling old mate Mendelsohn in the Australian psychopath export business.

There have been multiple walkouts from recent screenings of The Nightingale, the confronting second feature from The Babadook director Jennifer Kent, in which Herriman plays a violent British soldier in 1825 Tasmania. He plays an abusive puppeteer alongside Alice in Wonderland star Mia Wasikowska in dark fairy tale Judy and Punch, hitting cinemas later this year.

But first, he takes on arguably the most high-profile role of his career, in a small but pivotal role as serial killer Charles Manson to Margot Robbie's Sharon Tate in Quentin Tarantino's keenly awaited Once Upon a Time... in Hollywood. Uncannily, he'll also play Manson in the second series of Netflix hit Mindhunter. "It's kind of reached saturation point," he says of his newly-acquired mean streak. "[Since] I started going to America, I generally play people who don't shower, are psychos or are addicted to drugs, and this year it's got to the point where I'm like, "OK, I'm not going to do these roles for a while"."

Now aged 49 and in the midst of a career renaissance, it's good to have the choice. He's remarkably candid about the leaner times. "You have to have some kind of fall-back, and in my 20s that was an office job," he says. Working for the same insurance firm as his father, he spent the best part of a decade in a suit and tie, thankfully allowed to clock out whenever he booked an acting role. "I got to 27 and I said, "I don't know if I should stay in this office, because I feel like I'm never going to leave"."

I generally play people who don't shower, are psychos or are addicted to drugs.

Damon Herriman

These days the quiet periods are taken up with more career-appropriate voiceover work, and he's pretty sanguine about the possibility of roles drying up. "I feel a bit guilty saying that, because I know there are people who genuinely live for acting, and I don't want to belittle that at all, but it would also be disingenuous of me to pretend that that is who I am. I love this job, don't get me wrong. I love the people. It's a pretty cool way to make a living. But there's something about having fallen into it as a kid with parents who kept my feet on the ground that's a very different experience from going to acting school, where obviously it becomes part of your very being."

It was Herriman's father who first suggested introducing is son to an agent. Initially, he loved the pocket money but his hormonal insecurities enacted a temporary career hiatus. "As soon as I started high school, I had no bug at all," he recalls. "I completely lost interest, and it wasn't like something had gone wrong. I just felt a bit weird being a teenager and an actor. I assumed I'd get a regular job."

Yet acting continued to call him back. His first American role came in 2005 horror movie House of Wax, which was filmed on the Gold Coast with a US cast including Paris Hilton. "That one was incredibly fun," Herriman says. "Paris was everywhere then, so it was really bizarre. She was an incredibly smart, fun, friendly person and I'd tag along whenever they went out to nightclubs. She'd get this roped-off section and people would be screaming her name. I'm just sitting there going, "How did I end up in here?"."

At the age of 33, he decided to give the US a "proper" go. "I'm very much a realist, but I'm also a terrible regretter, and I knew this would probably be my only shot."

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It was another 15 years before he got the mythical call from Quentin Tarantino. "People overuse the world surreal, but I'm allowed here, yeah?" Herriman asks. "These career changes creep up on you a bit. It's not like one day I'm doing an episode of Water Rats and the next I'm in a Tarantino film. It's a slow process."

Playing double Manson roles certainly dispels his "good boy" image. "I did every bit of research I could," he says of playing the murderous cult leader. "I've never played a real person that's super-familiar to everybody before, so you want to get things like his gait and his voice, obviously, but it's that fine line between impersonation and capturing someone enough so you can trick people into believing it."

I ask Herriman whether his approaching 50th birthday has him reassessing things. "I don't think about it too much, but you can't deny the date on your driver's licence," he cackles, then pauses. "You know, I never got married, I haven't had kids, and I'm still open to both of those things. I'm also very realistic that I'm getting on, and I've been so busy with work the last year I haven't noticed it as much."

Another pause. "If at 25 you had told me I wouldn't be married with kids by 35, I would have been, "What? That's crazy." Time just keeps moving. You can't stop it. I remember being at my dad's 50th when I was in my 20s and, you know, I think the acting lifestyle keeps you younger at heart. I don't feel any different from when I was 30. But I am. So I have to face that reality."

Nice guy or nasty, a desk job in insurance is probably long behind him. "I might try and avoid the office if possible, but you never know in this business."

Once Upon a Time … in Hollywood is in cinemas now. The Nightingale is released on August 28, Judy and Punch releases November 7.