Three consecutive rap albums into the game and Aussie rapper-turned-singer Allday – born Tomas Gaynor – has shifted his own paradigm with the release of his fourth LP, Drinking With My Smoking Friends.

A mostly guitar driven rock album packed with melancholic vocals and sentimental riffs, the ten-track record— due out on May 28th— boasts a distinctly indie-rock feel; a sliver of which can be heard on the lead single, “After All This Time”. 

While Allday’s sound has previously infused doses of folk, rock and 90’s rap, his latest album is especially anchored in this new genre of music. From Stolen Cars to Void, there’s an aching sentimentality in his vocals that— when complemented by head-bobbing guitar strings— render an anthemic nostalgia to the record’s vibe. Such newly created melodies not only showcase the creative evolution of Allday’s singing and songwriting skills, they also unveil a previously unseen romanticism within his persona. 

As sudden as this shift in sound may be, the melodic transition is seamless, the delivery is smooth, and Allday retains the same off-the-cuff demeanor that is intrinsic to his style and undeniably magnetic. Between the new album, an upcoming Australia-wide tour, and a highly anticipated performance at the Great Escape Festival this year, Gaynor retains a surprisingly calm and low-key charm. On an early morning Zoom chat, the Sydney-based lyricist opens up about his dreams of collaborating with Prince, the Bonnie & Clyde-type theme to his album, and navigating life in a “panicked cruise control” mode. 

I heard an interesting story about you as a child, learning to play clarinet. How did that go down? 

I only played it to get into the Ensemble. In year 5— I was like 10 or 11 years old— and I had this girlfriend, and she played in the Ensemble…So I just wanted to learn to play the clarinet so that I could have some more alone time with her…I didn’t really stick at it…I just didn’t want the other boys in the ensemble getting too much alone time with her. 

Sneaky move…It seems like over the last few years your sound has taken on more of a folk vibe, with slices of other influences. Do you ever include the clarinet within any of your song production?

There’s a guy who plays saxophone — he’s actually from L.A., and his name’s Jacob Scesney— and he’s a wizard…practices everyday, and plays jazz. So when I need something done, I’ll just go to him and he’ll play something mega. On the new album, there’s this song called Door, and he plays a solo in it. 

As I’ve recently become more familiar with your sound, I was intrigued by how your music is classified— it’s classified as Hip-Hop, though to me, it reminds of folk. Your earlier tracks though have a more hip-hop vibe. 

Well, yeah I moved away from it [Hip-Hop], but I started as only a rapper…I sort of just like go back to rap randomly, with like one rap song. But yeah, it was kind of like pop rap back when started…I guess because over here in Australia, that was the thing that was happening. Everyone was listening to music that was like “Boom Bap Bop Pop”, like Jurassic 5. You remember that group? 

Of course! What’s Golden was my jam. 

So that was the thing in Australia when I got started, “Boom Bap Bop Pop”. 

I read that you started out in music in a group called Sissycunt. Tell me about that…

To be honest, I think that’s just the Wikipedia. I don’t think that’s true. 

It is Wikipedia. 

I’m sorry. People always ask me about that. I was in a few bands, but I don’t remember if they were called Sissycunt…I don’t think they were…but it’s kind of a good name. 

It’s catchy— it has a certain ring to it. 

Maybe I should work with it…But yeah, I started out in a couple of bands with my mates. I always had this rock side that I wanted to follow. A lot of my mates played guitar, or did rock stuff. And then I had the hip-hop stuff…I was in these bands, but then usually, at a certain point someone would say, “Well you’re not very good at singing, so maybe we should just leave this band thing for now.”

But I like your voice— it transports me to a nostalgic place. It actually places me back in my final year of University— I went to RISD, and your music for some reason just takes me back to my years at art school. 

I heard Paul Simon once talk about his voice and say that no matter what he does, his voice always sounds really sincere. Like he can’t do a silly song, because he’ll just naturally sound sincere. It’s probably something similar with my voice— even if it’s not the best voice, it’s at least sincere. 

Sincerity counts for something. There are a lot of legendary singers— Diana Ross, for instance— she’s no Whitney Houston— but there’s a sincerity in her voice…But for you, it’s not just your voice that’s sincere— it’s your whole presentation. Something about you strikes me as authentic and unapologetic in an off-the-cuff or unplanned kind of way. 

I’m definitely unplanned…Um— Diana Ross? I didn’t realize she wasn’t a good singer. She sounds good to me. 

I’m not saying she’s not good. She’s just not Whitney. And Whitney is my metric for female vocalists. 

As well she should be. I was listening to a song by Celine Dion the other day— because it was like, I always knew that she was massive, but “What’s the whole hype?”. And Celine Dion’s really in the area of Whitney Houston…She’s pretty cool. 

Celine is definitely in that orbit…Who would be your dream collaboration? It could even be someone dead. 

Celine. [Laughter] No…it would be Prince. It was a shame that he passed away so young…Well not so young— he was like 50. 

Him and Michael [Jackson]. With an extensive background performing in groups, how did you become a solo artist? 

I was in a band that kicked me out for not being good at singing, so that was one thing…And it kind of just tumbled from one thing into another. I was mucking around doing different stuff. I had moved to Melbourne from Adelaide, and I had just made a song or two, and then a few people were passing it around, and it was getting a good reaction so I decided to do another song. It wasn’t so much of a big plan, like “I’m gonna make it”, or whatever. It was, “oh, people like this”. And I didn’t have anything to do— like I didn’t have a plan in life. So I was just like, “Man, I should just follow this as far as it goes”. 

It sounds like you do a lot in cruise control mode. Like “hey, I’ll put this out here, and we’ll see what comes.”

Yeah, but it’s like panicked cruise control. I was like, “Fuck, I have nothing going on for the future”. [Laughter]. So yeah, I was in cruise control, but I was panicked.

That’s a whole vibe: panicked cruise control. [Laughter]…In a 2018 interview, you said that you didn’t really have a mentor in the business. The tricky thing about the music business is that it’s a real business, and sometimes challenging to navigate…In the time since then, have you gained a mentor, or someone to show you the ropes along the way?

I do have my manager, who has always been good— same guy all along, since my first video…And I haven’t gotten signed into awful deals, for the most part. He was savy…And we have a pretty cool music community in Australia as well. I’m very friendly with a lot of the artists here, so I can always ask someone about a particular person, or whatever…Maybe not one particular person as a mentor because when I first came through in the music scene here— as far as rap— I was polarizing. Most of the older rappers were like, “Fuck this guy!”. 

So they were heavyweight hating on you?

Big time. Because for when I came through, I was the most effeminate rapper in the history of Australia…But now there’s kids with green hair, you know what I’m saying? So it’s changing…

Maybe they just couldn’t deal with the new face of rap— so there was resistance. 

That’s what it’s always like, I guess. If people aren’t resisting, maybe you’re not doing anything different. 

When I was 16, a teacher at boarding school told me, “If everyone likes you, that means you’re not doing your job”. 

Wow. Interesting coming from a boarding school teacher. 

Yep— it reshaped that part of my perspective…You know, your music vibe— and even the ease in chatting with you— you remind me of someone I would’ve met in art school. There was something very familiar. 

Thank you. I mean, I did go to art school for a bit, as well. 

What did you study in art school? 

I did the first year— so the school that I went to, in the first year, it’s a little bit of everything. A bit of life drawing, a bit of painting, etc…And there were some people who were just amazing at it, right away. Their parents were already famous artists. So I was like, “Damn, these guys are so good, and I’m kind of shit. Maybe I should just go do something else”. So I dropped out…But that was before music was happening, so I was just looking around to see what avenue was for me. 

And you found it. 

Lucky me. Yeah. 

Fortune favors the bold— and that was a bold move. To drop out of art school and pursue “panic cruise control”. [Laughter]…Your music has a romantic streak to it. Are you a hopeless— rather, hopeful romantic? 

I think so…it’s always seemingly a way out for the characters presented in my music. Romance is always there as the escape. One reason is it’s that it’s easier to write songs within that mold. Romance being the answer is a nice way to finish a song. And it’s a nice fantasy. 

It is a nice fantasy. You have a lovely way with words— well, you’re a writer, so of course you do. 

Actually, I have to. [Laughter]. 

That’s true. Can we talk about your new album? It has a Bonnie & Clyde feel to it—without the violence. 

Without the violence…yeah. Should I go from here, or do you want to ask away?

You take it from here. Cruise control. 

Basically, I had a couple of ideas in my head. I grew up in a small city— Adelaide…but you know the small city thing, there are certain undercurrents and certain dark feelings in the psyche of a small place…Although this is a story, there are certain elements of truth to it. Like there are dark parts about where I grew up that make me like, “Alright, I’m getting on the highway”, connecting when I was younger. So when I write that stuff, I’m telling it like a story, like I want it to be a movie; but there’s definitely an element that I could reach to for truth. 

And which song is your favorite from the album?

Right now it’s Bright. The song sort of takes off really slowly, but it’s like, “Oh I got that right.” And also, Butterfly Sky, It’s really slow, but it’s got some cool imagery in it— like wild cowboys and whirlwinds, and all this shit that when you listen to it, it transports you…So maybe Butterly Sky. 

My favorite is After All this Time. 

I love that song, but I feel like I didn’t quite get it right. It was the first song that I did, and I was changing genres…And like, I wanted it to be more like The Cure, and more 80’s. 

For me, that’s exactly what it is…one last question for you. I watched an interview with you from 2018, where you were asked how you’d like to be remembered, and you responded that you didn’t really care about how you’d be remembered. Has your perspective on your legacy— or the legacy that you will have— changed since then? 

I mean it would be nice to be remembered for making cool songs. You spend your life doing something, you know…I work pretty hard— as hard as I possibly can on it. So if people remember the songs, that would be mad. If they don’t, I’ll be dead any way, so what will I know. 

‘Drinking With My Smoking Friends’ is out now. Follow Allday via @alldaychubbyboy

Interview Constance Victory

Photography Sam Wong