I Enjoy Music is a callback to old-school music blogging
A conversation with Molly Mary O'Brien about the state of music publications, the joys of personal writing, and how to get people to actually read things.
Today’s issue of PHONE TIME is a conversation with writer and video editor Molly Mary O’Brien. O’Brien runs the music blog I Enjoy Music.
Amid growing discussion about the impact of recommendation algorithms and AI on the music industry, Molly Mary O’Brien’s blog I Enjoy Music is an ode to the value of personal recommendations and good old-fashioned conversation.
Earlier this month, I spoke with O’Brien about her start in music writing, how social media has changed music discovery, and the blog’s accompanying digital music label, I Enjoy Remixes. This interview has been edited for clarity and length.
PHONE TIME: Let’s begin with your background and how you came to start I Enjoy Music.
MOLLY MARY O’BRIEN: I’ve always enjoyed music writing. I grew up reading my dad’s subscription to Rolling Stone. I was in high school-ish when music blogging first kind of became a thing, which was sort of a) the democratization of music writing, and b) the ability to share music online.
Obviously, digital music changed the way everyone accesses music. In high school and college, I was reading Pitchfork and Tiny Mix Tapes, early-ish online music publications. When I was a senior in college, I was like, “Okay, I’ve read enough music criticism, surely I can do this myself.” And I went on Craigslist and found this totally unpaid writing job for a website that doesn’t exist anymore. The history of music writing is like a graveyard of websites that, you know, go to nothing.
For a few years, I was writing about music online—not a professional, not getting paid for it. But I never had [a space] of my own. I think it was Covid that brought me to the idea of carving out a zone for myself online that would be whatever I wanted to write about music-wise. Not worrying about whatever the trend cycle was, anyone’s house style guide, or fitting someone else’s editorial voice.
I started I Enjoy Music two years ago, in June 2023. That was after doing some content creation for The Alternative, which is an amazing website, still underrated after all these years. That reminded me of how great DIY music and independently created music is.
PHONE TIME: You mentioned that having your own blog space enables you to write outside of what trend cycles allow for. How has that experience been different, or why do you think it’s been important?
O’BRIEN: In terms of the way popular music criticism, music news, and across-the-board digital content has boiled down, everything is now just the lowest common denominator. I don’t shade popular music websites for doing this, but it’s like, “The tenth anniversary of this album is coming out; it’s the 20th anniversary of this album coming out.”
I think personal conceptions of music are so much more interesting in comparison to this sort of generalized approach to music writing. For example, there’s a cottage cheese brand that I’m kind of obsessed with. They had shared on their Instagram that they had done a pop-up event in New York and the playlist that they played during it.
I was like, “I want to listen to this playlist, see what they thought was good to play at a cottage cheese event and write about it.” That is something that I don’t think anyone else did.
I guess uniqueness is important to me. Especially now, between the way content creation is and AI, it’s kind of people making copies of copies of copies. Personal expression and creating things that only maybe you have thought of is really important to me. In an ideal world, more and more people would be doing that, because that’s the kind of stuff that can’t be reproduced on a mass scale.
PHONE TIME: With I Enjoy Music, you’re talking to people who make music. You’re getting songs from people who are music enjoyers. And then you are also kind of writing about everything else related to music. How do you think about what to write about?
O’BRIEN: On one hand, talking to musicians directly is really important to me, especially because I do focus on musicians at the beginnings of their careers, or who are maybe not as big as they will eventually get. I think that comes from a weird sense of extroversion where I’m like, “It’s not enough to listen to music. How did they do that? Why did they do that?” I find those conversations to be at least interesting on a personal level.
In terms of deciding who to talk to, it’s a mix of outreach and inbound. I get pitched a lot of stuff, and I try to listen to as much of that as possible. I love when people send me things, especially unique pitches and weird email subject lines.
Some of it is externalized. I think interacting with the world and being proactive is also something that I value—being as receptive to any kind of stimulus or input as possible. One of the core values of I Enjoy Music is that music enjoyment is everywhere, because music is everywhere. Hearing a song out in public and Shazamming it and being like, “What is that?” Or talking to someone at a party and asking them what they’ve been listening to lately. Just trying to treat it more as this atmospheric, aura-type, living, breathing thing that exists for everyone.
PHONE TIME: I feel like probably with any form of culture journalism, it’s getting harder to write or place experimental things. How do you think the larger, maybe more mainstream or traditional music writing scene has evolved over time?
O’BRIEN: This question makes me think about how to get people to read stuff, which is hard with social media being the way it is. It’s important to me that it’s a blog, first of all, before it’s a newsletter or something that’s on social media. It’s just like a website you go to, and I’m aware that that’s not the coolest or most productive way to make a thing anymore. It’s a little bit old-school.
I feel like it’s harder to get people to read experimental stuff, because the way that most content gets disseminated these days is there’s got to be some kind of clicky, hooky thing, and it’s got to be extreme. I have a friend Ryan who runs a newsletter/Instagram page called antiart. Because he has really strong opinions, so he has no problem making a post being like “X artist sucks” or “I like this new thing that people don’t like.” I’m so envious of that kind of operation, because I feel like it is a way to take advantage of the way that people exist online now. People are very heightened and reactive.
I’m not saying that antiart is clickbait, but there’s a time when clickbait was a thing that people did. Then there was a backlash to the clickbait. Now, I’m like, maybe we need to revive clickbait again a bit. Being like, “Listen, I’m just trying to get you in the door. Once you’re here, you can read my weird thoughts.”
PHONE TIME: How much are you engaging with music-related content on social media? TikTok?
O’BRIEN: I was on TikTok a lot more, prior to when the ban kind of floated up. I’d curated a pretty great algorithm, and I found a lot of new stuff. And then I think I got burnt out on TikTok as a whole. I’m not anti-that in general, but I did find TikTok sort of melting my brain on a personal level.
I feel like Instagram is kind of a tough category to get eyeballs on, unless you’re making clicky headlines or Reels or whatever. There’s one example I wrote about, a French DJ duo, Jersey, who are brothers. I found them on my Explore page, there was a video with the caption “Nobody ever knows how to dance to 200 BPM.” And it was just this video of all these people bouncing around at hyperspeed. I was like, “What is this?”
In terms of general music media, I engage with it a pretty reasonable amount. I have a lot of newsletters that I receive, and it’s a good mix of personal writing and people who make playlists. I do have a print subscription to Rolling Stone again after all these years. I still read Pitchfork and Stereogum and bigger sites like that.
“I do think that the thing about getting into Cool Shit is you have to work for it a little. You have to recognize your position as an uncool person, and see if there's anything you can do about it.” — Molly Mary O’Brien, “!!! and music magazines and trying hard to find something cool”
PHONE TIME: Do you have any favorite pieces you’ve written for I Enjoy Music?
O’BRIEN: This year I went to a bunch of music festivals. I love music festivals so much. I’m a very late-in-life convert to them. I think there’s a lot of discourse about music festivals dying, or “they suck,” or whatever it is. I’m kind of a defender of the idea of seeing a band play in a big field.
This year, I wrote about going to Coachella and Kilby Block Party, which is a smaller festival in Utah. I was pretty proud of the recaps I did of both of those, because I really like experiential writing. Reading about other people, what they did, what they ate, who they talked to, just a very traditional concept of what blogging used to be like.
I also talked to Nora Nygard, who makes all kinds of music—experimental, pop-ier, ambient music. I talked to her about a project she did that was kind of emotional and personal to her. I’m really proud of that, because I’ve read a zillion profiles, but I hadn’t put pen to paper about how to do it to myself. So there was a combination of following tropes I was already aware of, and then hopefully trying to create something new.
PHONE TIME: What’s your vision for the future of I Enjoy Music?
O’BRIEN: I started I Enjoy Remixes, a kind of digital music label in tandem with the blog that I’m really excited about. That is my first foray into any kind of music creation. The way it works is I’m asking artists that I like to pick a friend or a colleague, and then remix each other’s songs. It’s been fun to facilitate that so far.
In the long term, I have a dream of maybe more sophisticated software or apps focused on community-building. One of the main formats of the blog is me getting recommendations from people for what to listen to. That culminates at the end of the year with asking a bunch of people what their favorite song of the year was, and listening to it and writing about it. I also have this feature called Music Moots, which is asking one person for one song. So I had this idea that maybe there could be some weird online community that involves getting randomly matched with someone, and you exchange songs.
PHONE TIME: I’ve started asking people what their level of optimism versus pessimism is about the web, so I’ll throw you that question as well.
O’BRIEN: I feel like I have individual moments of extreme pessimism. Focusing on music content in particular, there’s so much to fight against in terms of things turning into this world of slop. There was a recent story of an AI-generated band called The Velvet Sundown, with like 700,000 monthly listeners on Spotify, and people freaking out about that. [At the time of writing The Velvet Sundown now has over a million monthly listeners.]
I will go rogue and say I feel weirdly optimistic about at least personal music writing online. I do think there is an overall trend toward blogging, having newsletters, and trying to maybe break away from the social media grind of it all. I’ve got a blogroll on my website that shows there’s still plenty of people who are putting in the effort to do that on an individual level. I think the more slop there is, the more inspiration there will be to be anti-slop.
In the same way that I remember being in middle school and early high school and feeling frustrated with what was popular and what was accepted as good, that turned me into someone who sought out alternatives to things. I developed a lot of my personality and critical thinking skills based on that.
Even though there’s going to be this element of anything from AI-generated music to the consolidation of pop radio into like four songs they play over and over again on Clear Channel stations, there’s going to be inspiration for at least a certain subset of people to get a little more active about being choosy and seek out things they actually like, or things that feel different.
Find I Enjoy Music at ienjoymusic.net.
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