Kicking off with his 2019 debut single “Dirty AF1s,” singer-songwriter Alexander 23 has built a career wearing his heart on his lyrical sleeve, cultivating a rabid fanbase that fawned over his subsequent EP Oh No, Not Again!, including the viral single “IDK You Yet.” Along the way, he’s seen success alongside frequent collaborators such as producer Dan Nigro and fellow artist Olivia Rodrigo, the latter of whom helped write the artist’s latest track, “Hate Me If It Helps.” It was a returned favor of sorts, considering Alexander helped co-produce Rodrigo’s Billboard Hot 100 No. 1 “Good 4 U” (alongside Nigro) from her Grammy-nominated Sour, the success of which landed him on Billboard’s Hot 100 Producers Chart.
Now, Alexander is prepping for the upcoming release of his Dan Nigro-produced debut album and is currently on the aptly dubbed Sob Rock tour, a nationwide string of dates which has with the artist opening up for John Mayer, hitting Boston’s TD Garden for a two-night run starting Friday (March 4). Alexander spoke to Billboard about his penchant for penning emotional lyrics, working with Rodrigo and a recent stunt to promote “Hate Me If It Helps.”
For those unacquainted, how did you get your moniker? I know you’re from Chicago, so did the 23 come from the connection to Michael Jordan’s number when he played for the Bulls?
I grew up 20 minutes north of the city in a town called Deerfield which is way less sexy sounding than Chicago. But it was an amazing place to grow up and I go back whenever I can because my parents are still there. But I was also born on the 23rd so it was kind of always my number for that reason as well. But I think it’s certainly elevated being from Chicago, I’m a huge basketball and Bulls fan, so there’s definitely a strong connection there.
This past Valentine’s Day, you pulled a viral stunt where you had a skywriter write “Just Hate Me If It Helps,” an allusion to your new single, all over the skies of Los Angeles and it caught absolutely everyone’s attention, from Offset to Adam Levine. How did that come about, and can you tell me how that day unfolded for you?
It was something I had been wanting to do for a while and it came together super quickly. It was like, “Tomorrow’s Valentine’s Day, it’ll be a perfect time to do it.” L.A. was also the perfect place to do something like that, since everyone is looking for something to throw on their Instagram Story that’s interesting, unique, witty or stupid. So we hired someone I had no idea they were going to write so many times all over L.A. County. My phone just started going berserk. First it was friends asking me if it was me, and then people like Offset, Adam Levine and Iggy Azalea were posting it. That type of promotion can typically cost millions of dollars, but I think when you do promo the right way you can get it for much less. It went as well as it could have ever gone in any simulation of any reality. The most interesting aspect is that everyone thought it was Kanye West. My ego always tells me to correct them, but when I thought about it, it was the best thing that could ever happen, because then they’ll talk about it way more. So I let it go and let that narrative take over. It was fun to watch unfold. Originally we were going to write, “Just hate me if it helps” but then I figured we should say, “You can hate me if it helps.” It’s a little bit longer, but I think it worked better.
Let’s talk about the song for a second, because I’m looking at the lyrics and I think they are very of-the-moment: “I wonder if your therapist likes me. I guess it depends on how much of the truth you tell to her.” Just 10 years ago, a line like that would be unthinkable. What has evolved: lyric writing, or our general view of emotional and mental health?
I think there’s been kind of a paradigm shift in the way people listen to pop music. For a long time, people tried to connect to someone they aspired to be or dreamed about being. But now people want to feel understood in their current state, rather than aspiring to be in a different state. That’s been something that I personally have always listened to music for, and when I started writing it was really important to me to be as truthful as I could. People use music to control and understand their emotions.
You were writing songs that fit this bill long before they became trendy. If you released this same song ten years ago, maybe it wouldn’t fit into the landscape as well as it does now. Or maybe it’s that you and your pop mafia – or popfia, if you will – of Olivia Rodrigo, producer Dan Nigro and maybe even Conan Gray are part of a new class that seems to be changing the face of pop.
What I’ve learned is that chasing trends is a futile exercise. You’re never going to do it better than the people who are doing it at this moment. Second of all, even if you do by chance master it, by the time you do that there will already be another trend. The best thing you can do is to be yourself and hope that people will be ready for it by the time you put it out.
In the middle of “Hate Me If It Helps” there’s this sort-of staccato crescendo where you hit some individual notes, slamming on them out of nowhere, and then going back to the typical rhythm of the song like nothing happened. Where did that come from?
I just wanted the production of the song to echo how dynamic the feeling is. In the song it’s about a willingness to be the bad guy, battling back and forth with yourself, and the give and take of moving on and getting over someone. I wanted that to be felt in the production as well and for it to be as jarring as it could be, so it just made sense. It also came about because after going on my first headline tour this past fall, I was really inspired by the way things felt live. I really wanted to bring some of that energy into the actual recording.
Speaking of you, Dan and Olivia, what’s it like to have a group of creative collaborators pop off at around the same time and tap into the mainstream consciousness? That’s a rare thing as I know you were all on the come-up around the same time.
It’s unbelievably fulfilling, is the best way I can put it. A lot of people in interviews ask me, “Who are you inspired by?” There’s obviously a ton of inspiration from older musicians, but for me there’s nothing in this world more inspiring than watching your friends win because you see the work they’re putting in. I’ve been in the studio with Dan super late after we started super early, and I know how hard Olivia works not only at her craft but all of the stuff you have to do after you put a song out. So it’s been such a joy to watch.
When you were just getting started, Olivia was just singing on demos you’d produce, right?
We met through mutual friends before she put anything out. I remember working with her for the first time. She left my house and I was just like, “This girl is going to be the biggest artist in the world.” The songs simply pour out of her and I think she has the characteristics that all of the greatest artists do, which is that they know what they like. It’s not about what your taste is, it’s that you have taste. They know what to say yes and no to. For her to come to my home studio when she was just 17 and be so sure of herself and so confident, it was a telltale sign that she was going to have an illustrious career which has obviously played out in real time.
You’re credited as a co-producer on “Good 4 U,” one of the most successful pop songs of the last few years. Now Olivia is credited as a writer on “Hate Me If It Helps.” Why do you think that this creative relationship works so well?
I think it’s just the trust thing, really. A song like “Hate Me If It Helps” is a really sensitive song and a real song for me. It wasn’t the easiest to write and wasn’t the easiest to make sense of. You want to do that with someone you trust emotionally, and it obviously helps when that person also happens to be one of the best songwriters in the world at the moment.
When it comes to “Good 4 U,” what was the process like co-producing it?
It was awesome and just honestly a fun process, because Dan (Nigro) and I had worked together for a bit before that, so we had a great working relationship. Dan is just so good at production; he’s so patient and so willing to try new things. There are some producers, songwriters or people in every field who think outside the box. Then there are those who think outside the outside of the box. He falls into that category, and this is why I worked on my upcoming album with him. He gets the best out of you when you’re working with him. It makes you really, really push yourself. So it was a fun, easy but still challenging experience.
You write about things that are hard to talk about, let alone sing to an audience about. Can it be difficult to perform and remind yourself of these heavy moments all the time? Does it bring you back to that place?
I think there’s a balance to be had that I’m getting better at approaching. To a certain extent, the songwriting process for me is the last step of the grieving process, or whatever feeling I’ve been through. So it’s a release in a way. There are obviously some songs where whenever I perform them I’m always going to feel something, no matter what and no matter how long it’s been. But I think it’s a good thing because it puts me in a place to give a performance that could be compelling. It’s obviously emotionally exhausting sometimes but I think it’s worth it. I want the performance to feel as compelling as the feeling that inspired the song.
Do you ever have thoughts, emotions, lines, ideas or sentiments that are just too raw that you avoid putting them in your songs? You just can’t go there?
I have in the past, but “Hate Me If It Helps” also marks a new territory for me. I’m going there and it’s definitely an experiment. I’m also okay with the possibility that in a year I’ll change my mind. Only time is going to have to make that decision for me. But I am going there, because why not? I think it’s so tempting to bundle those feelings up, hide them away and convince yourself that it’s just you. But I think what I’ve seen over my short career so far is that the more specific I am and the deeper I go, the more relatable it ends up being and more people see themselves in that. It may not be the exact version of their story, but people can find their own truths in it.
You’re on tour with John Mayer. First, do you call him John, Johnny or Mr. Mayer?
(Laughs) Mr. Mayer is good.
How’d that come about? When thinking about the line between his career and musical voice in his early days and your own career and style now, it seems pretty clear. He was a singer-songwriter with a guitar singing about the feelings in his heart.
I didn’t know about this tour until two weeks beforehand. It came together really quickly and I still don’t know all the details on how it exactly happened. It’s obviously an honor. He’s inspired me in so many ways and continues to do so and it’s cool to kind of pick his brain a bit. His fans have been super gracious. They care about the same stuff that I care about. There’s a huge attention to musicality at these shows that is really cool to see. We started a friendship there I’m certainly grateful for. He’s made it incredibly clear to say that he’s here for me both professionally and emotionally, which is really, really cool.
