Backstage Conversations: Charlie Pittman Before His Sydney Headline Show

PHOTOS BY SAVANNAH GALLIMORE

Fresh off the release of his new EP okay.again?, Charlie Pittman has been bringing his deeply personal songs to the stage. Pleaser sat down with him ahead of his headline performance at The Vanguard in Sydney, the second stop of his Australian tour. In conversation, Pittman talks about performing brand-new music in front of audiences, what goes into crafting a setlist that tells a story, and why surrounding himself with good people is essential to life on the road. As his live shows continue to grow, Pittman remains focused on creating moments that feel both intimate and unforgettable. With okay.again?, he’s proving that his music isn’t just meant to be heard, it’s meant to be experienced.

PLEASER: You just played your first show since the release of your new EP, okay.again?, how was playing the new songs live?

Charlie Pittman: It was nice doing Melbourne first. Melbourne has a different vibe than Sydney, and since I live in Sydney, having Sydney as the second show felt right. Melbourne was almost like a test run to see how the songs would land. It just made me more excited for the Sydney show.

Do you get more nervous playing in front of people you know?

CP: Oh, for sure. These kinds of venues are so intimate that you can literally see everyone. I’m looking around thinking, “that’s this person, that’s that person.” It makes me more nervous, but also more excited.

Do you have any preshow rituals?

CP: Honestly, no. I’m the most non-rock-and-roll indie artist. I just drink a ton of water and avoid food. I can’t stomach anything past 3 p.m. on show days.

How does performing your songs live compare to recording in the studio?

CP: A million times better. In the studio, you’ve got endless takes, always chasing perfection. Live, you get one shot.

That pressure makes it more fun and often brings out the best version of the song. It’s so much better playing live because people are actually watching.

When you're in a studio, it’s just you, the producer, and a mic right in front of your face.

Since your new EP is so personal, were there any songs you felt nervous about playing live?

CP: Yeah, I was a bit nervous to see the reactions to “Casual” and “How I Feel.” But even though they’d only been out for two days, people were already screaming the lyrics back. There’s a moment in “How I Feel” where the backing vocal says “get yourself together,” and the front two rows shouted it at me; that was wild.

How do you prepare your setlist?

CP: I want the show to start with a bang and have parts throughout where it comes to the more chill moments. I know I have some emotional songs in the set, so I craft it in a way where it doesn't go super loud, then quiet, then loud again. I try to take the crowd on a journey and make the whole thing flow seamlessly, even transitions between songs. We have one break in the middle of the show after my most emotional song, “dog, black,” where I let the crowd choose what song I cover. I feel like it’s a nice break-up to lift people up again after that song.

How do you let the crowd choose the cover?

CP: I give the audience two options and let them decide with noise. Yesterday we did Miley Cyrus’ “The Climb” mixed with Katy Perry’s “Firework.” I love picking songs that are nothing like me and making them my own.

You were on “The Voice,” how was that experience and how did it help you with your live performances?

CP: I’m proud of it. I treated it as a platform to reach more people. I went in saying, “I’m a songwriter, I write for people and myself,” and tried to gain an audience through that.

As for performing, it definitely helped me be comfortable onstage. Performing under that much pressure, with cameras on you, made normal shows feel less intimidating.

What is one thing you want people to take away from your shows?

CP: I just want them to feel something. Maybe they connect to a lyric, or maybe they just had a fun night.

There are so many songs I write, and I don't think about how they might resonate in different ways for other people. Then I play them live, and people come to me and say it moved them, which makes me feel really supported. I just hope whatever someone takes away is a good feeling.

Have you had any “pinch-me” moments while touring?

CP: Honestly, every time I do a headline show, especially in Australia. I didn't grow up here, so when people show up, I think, “This is crazy, what do you mean you're all here to see me?” In the UK, I was playing shows, and it was mostly friends and family. But when I’m here, I know like two people, and everyone else is a stranger or people I've seen at other shows. Knowing people show up for me as a headliner is always a pinch-me moment.

Do you have fans who come to multiple shows?

CP: Yeah, some people do Sydney and Brisbane, others fly interstate for shows. A few even come to all the shows. It blows my mind, but it also validates me as an artist, like, it was good enough the first time that they wanted to come again.

How do you keep your energy up while touring?

CP: I’m lucky to have an amazing band; they’re the best people. Same with the support acts, who I pick because I’m genuinely a fan and they’re good vibes. That energy keeps the whole tour light and fun.

What’s been your most memorable show so far?

CP: There's been a lot of amazing moments. My show at The Lansdowne Hotel last year was pretty memorable because it was my first Australian headline. It was really cool seeing the friends I had made in Sydney and the fans blend into this amazing energy.

What advice would you give to young artists?

CP: Be brutally honest in your writing, even if the song never comes out. Say what you need to say first, worry about the meaning later. And for performing: Remember the audience wants you to do well. They’re rooting for you, not waiting for you to mess up.

What’s the biggest lesson you’ve learned from performing and touring?

CP: To live in the moment. I’m always looking ahead to the next thing, but I need to remind myself that at some point, this was the goal. So I try to be present; otherwise, it all flies by.