In our recent zoom interview with singer, songwriter Charlie Pittman, we learn that he has never taken the conventional route. Born in Australia, raised in the UK, and now back Down Under chasing a career that’s blossomed faster than he ever imagined, the 25 year old singer-songwriter is on the cusp of something big. With the release of his second EP okay.again? and new single ‘how I feel?’ (out today, September 19), a national tour, and international dates locked in, Pittman is finding his voice in a way that’s both bold and vulnerable.
MORE ABOUT CHARLIE PITTMAN AND HIS NEW MUSIC
Pittman wasn’t raised in a musical household, but when he picked up a guitar at 11, the spark was undeniable. Teaching himself to play and write, he began performing in school plays before training as an actor. But the pandemic derailed that path and pointed him toward music. “I started posting originals on TikTok when acting auditions dried up,” he recalls. “That audience gave me the confidence to take it seriously. Without that downtime, I probably wouldn’t be releasing music now.”
He packed up his life in London two years ago, landing in Sydney for what was meant to be a six-month stay. “I thought I’d just use my Aussie passport for a change of scene,” he laughs. “Now it’s been two years and I feel like the music community here has really taken me in.”
Blending indie rock with alt-pop, okay.again? is Pittman’s most cohesive work to date. The six-track EP, recorded in Nashville with producer Jonathan Class (Medium Build), intentionally tells a story, the cyclical arc of love, heartbreak, and renewal. “The whole EP is a loop,” he explains. “The same motif at the start comes back at the end, like you’re right back where you began. It’s about how relationships are cycles, you get yourself together, then go through it all over again.”
His latest single “death row” sets the stage. Co-written with London collaborators Itamar Lapidot (Good Neighbours, Raye, Joel Corey) and Francesca Morris, it captures the quiet devastation of knowing a relationship is over before anyone says it aloud. “There’s guilt in holding feelings back,” Pittman says. “The metaphor of death row felt powerful, like you’re the executioner waiting for the inevitable.” The track arrives alongside a live performance video shot in Melbourne, showcasing the raw intensity that’s become his calling card.
Pittman admits he once censored his writing out of fear. “I worried about what people would think,” he says. “But I realised the songs only really mean something when they cost you something.” That shift toward unflinching honesty is stamped all over okay.again?, six songs tied together by lyrical threads, where moments of intimacy give way to soaring choruses and chaotic guitar breaks.
Though recorded in Nashville, Pittman’s creative process remains humble. His home “studio” is just an SM7B mic, a Focusrite interface, and a baritone Fender, with demos often starting as voice memos. “You don’t need much,” he grins. “Sometimes the rawest idea is the best.”
On stage, however, the songs become something bigger. Fans can expect an exhilarating mix of intimate moments and full-throttle energy on his okay.again? national tour, which kicks off September 20 in Melbourne before hitting Sydney, Brisbane, and Perth. “When I write, I’m already imagining how it’ll feel live,” he says. “I love creating those singalong moments – and maybe even sneaking in a chaotic guitar solo or two.”
From there, the momentum doesn’t stop. Pittman will perform at SXSW Sydney, then jet to the UK in October to support indie-rockers The Manatees, followed by a slot at Live At Leeds Festival on November 15. Looking further ahead, he’ll showcase at South by Southwest in the US before continuing his run across the UK and Europe.
“I just want to tour this music as far as I can – the US, Asia, South America, everywhere,” he says. “And I’d love to make an album. As long as people want to listen, I’ll keep playing.”
For Pittman, okay.again? isn’t just an EP, it’s a statement of intent. Vulnerable, cyclical, and bursting with ambition, it captures an artist in motion, finally finding his place in the cycle.
Watch the official music video clip ‘how i feel?’ below
CHARLIE PITTMAN ‘okay.again?’ AUSTRALIAN TOUR DATES
Saturday September 20 – The Workers Club, Melbourne, VICwith specials guests Pretty Bleak & Effie Isobel
Sunday September 21 – The Vanguard, Sydney, NSW
with special guests byjae, Sam McGovern
Thursday September 25 – Lefty’s Music Hall, Brisbane, QLD
with special guests Pretty Bleak, Repeater
Saturday September 27 – Milk Bar, Perth, WA
with special guests Sam McGovern, Eliane
October 15-18 – SXSW Sydney, NSW
UK SHOW DATES
Wednesday October 1- Lending Room, Leeds, UK (supporting The Manatees)
Friday October 3 – Cluny 2, Newcastle, UK (supporting The Manatees)
Saturday October 11 – Omeara, London, UK (supporting The Manatees)
Saturday November 15 – Live At Leeds Festival, Leeds, UK
For all touring and ticket information HERE
‘okay.again?’ EP OUT FRIDAY SEPTEMBER 19
AVAILABLE TO ADD/ORDER NOW HERE ON ISLAND RECORDS AUSTRALIA
FOLLOW CHARLIE PITTMAN HERE