What’s Frank Ocean’s Best Song Ever? Welcome to ‘Last Song Standing,’ Season 2.

Welcome to Last Song Standing, a show from The Ringer and Dissect built on a simple premise: Two hosts figuring out an artist’s greatest song by debating their way through every album in their discography. Season 2 tackles one of the most gifted singer-songwriters of his generation, Frank Ocean.

Join Cole Cuchna and Charles Holmes as they debate their way through Frank’s catalog. This week, they kick things off with Frank’s 2012 studio debut, Channel Orange. Which song will prevail? The time-traveling strip club hymnal “Pyramids”? The “Bennie and the Jets” for the Tumblr Generation, “Super Rich Kids”? The taxicab confessions of “Bad Religion”? Be sure to listen to the full episode here and subscribe to the Dissect feed to hear how this sparring match plays out.

Below is an excerpt from Episode 1.

Why Frank Ocean?

Charles Holmes: Cole, we had a lot of debates behind the scenes about which artist to pick. Are you as pumped as me that we’re doing Frank Ocean?

Cole Cuchna: Oh my God, I’m so excited. I’m so glad this is the one we landed on. I love his music. I’ve done a season on him for Dissect. People know this. I’m curious to know why you’re excited to dissect Frank Ocean.

Holmes: I think every person has an artist that is the artist that helped them come of age. When you’re a teenager, this is the music that you’re listening to, teenage, college years. And I think Frank Ocean was definitely one of those artists. For me, where I had grown up loving R&B artists, but they were my parents’ artists or they were my cousins’ or different people. And Frank Ocean was one where I’m like, “No, I discovered him.” I remember going on Tumblr. I remember downloading the .Zip file and putting it on my iPod.

Cuchna: What I don’t get to touch on for Dissect is my opinion. Dissect’s a celebration and analysis. I’m excited to give my opinions about Frank Ocean’s music a little bit more, but I think as we live through the Frank Ocean experience, these last 10 or so years, he definitely has one of the most, if not the most, interesting career arcs that I’ve personally lived through. It’s just so unstandard, unorthodox, so unpredictable.

What makes Channel Orange special?

Holmes: Channel Orange was released on July 10, 2012. It’s Frank’s debut studio album and went no. 2 on the Billboard 200 with 131,000 copies sold in its first week. The project spawned five singles, including “Thinkin Bout You” and “Pyramids.” And at the 2013 Grammys, Channel Orange was nominated for Album of the Year, Record of the Year, and Best Urban Contemporary Album. Now, those are the facts of the album. But Cole, what would you say are thematically the concepts that really take us away on this debut of Frank’s?

Cuchna: At least how I think about it, it’s implied in the title, but Channel Orange is a concept album that plays like someone is flipping through TV stations. So each song is a self-contained story that functions—at least how I think about it—like a single episode of a TV show. Frank actually told Rap-Up at the time, he said, “It’s about the stories. If I write 14 stories that I love, the next step is get the environment of music around it to best envelop the story.” So stories here are critical. So for example, you have a song like “Crack Rock,” which tells a story of a broken home devastated by addiction.

And a song like “Pyramids” is like a surreal time-traveling allegory about a man in love with a former Egyptian queen turned sex worker. But what many of these stories share is this underlying theme of unrequited love, and this stems from Frank’s own personal life. Right before the album came out, he posted on his Tumblr that orange is the color that reminds him of the summer that he first fell in love. And this was a super formative relationship for him. It was his first love and it was also his first heartbreak.

Frank expressed how he felt to this person and they told him that they didn’t feel the same way. So he was absolutely devastated, and he channeled these emotions into his music. He said, “I wrote to keep myself busy and sane. I wanted to create worlds that were rosier than mine. I tried to channel overwhelming emotions.” So really at the heart of the album is this feeling of unrequited love. And the idea is that no matter what Frank does, no matter how many TV stations he flips through, he always returns to his memories of this lost love. He always returns to Channel Orange.

Remember the Blog Era?

Holmes: So what I want to ask you after that beautiful, beautiful breakdown is when did you get into Frank Ocean? Because I was a blog boy at this time. I was on Nah Right, 2 Dope Boyz. I was infecting my parents’ computers with so many viruses, just downloading tons of music. Frank Ocean was definitely one of those artists where I vividly remember when I downloaded the Nostalgia, Ultra as a mixtape. I’m interested because you are a little bit older than me and I believe you probably would’ve been around either late high school, early college, and that was around the time when you went into your pop music black hole and were completely on a classical bender.

Cuchna: Yeah. I’ve shared this a bunch, but when I went to college, I was studying classical music and I kind of just shut off every other genre of music. And so I missed, ironically, a lot of the albums and artists that I cover now. One of which was Channel Orange. And so I missed the whole Frank Ocean experience. I missed his come-up. I’d heard his name, especially when he was on Watch the Throne and stuff. But it wasn’t until actually Blonde came out that I went back and really listened to Channel Orange.

So my experience of Frank Ocean is very backward and we’ll probably talk about this. A lot of ways it informs my experience of Channel Orange because I fell in love with Blonde. Blonde is my album. I absolutely love that album. Channel Orange is a little bit different relationship for me, obviously great and we’ll talk about it, but I really fell in love with Frank Ocean and then I went back.

We won’t call it PBR&B, but …

Holmes: Frank Ocean comes on the scene when R&B was just in the doldrums. What Usher’s Confessions did, becoming one of the biggest albums released ever, was definitely this watershed moment for popular Black music in the 2000s. I think it cast this big shadow over the rest of the genre. What also casts a shadow is that I think we underestimate how much human connection and love changed at this time. We’re getting social media. The internet is readily available.

We have iPhones in our pocket for the first time. This is at a time when Tumblr is becoming a thing and Twitter is becoming a thing and dating apps. You have this cadre of artists, Drake, the Weeknd, Frank, who are trying to basically come to terms with how do you sing about love in a non-corny way, in a world where our conception of dating, our conception of connecting with people is changing radically.

And I think Frank Ocean was one of the artists that hits that mark perfectly, where you needed someone to shake up R&B. It could no longer be this thing where, “Hey, yo, here’s 26 jams.” Not that that’s all of R&B. R&B is a vast genre that I love and you have the Soulquarians. You have all these different types, but after Omarion and Lloyd and Usher and all of these places, I think that there was a need of, “All right, we need something a little bit different.”

The Tumblr letter, 11 years later

Holmes: I think the other thing that’s important to talk about in this album is the Tumblr letter that he drops on July 4. So I’m assuming you did not read this letter in real time?

Cuchna: Not in real time. I do remember hearing about it. I do remember it being a big deal, but I wasn’t entrenched, so I didn’t really understand the impact of it. But looking back as me studying almost like a history event, it seemed very important, but I’m definitely curious to hear your experience of it in real time.

Holmes: It was definitely a massive moment. The best way I could describe to you is just the feeling of it was I had my driver’s license and I was listening to Channel Orange and one of my cousins quite literally was like, “Yo, turn that shit off.” And I’m like, “Why?” And he’s just like, “Yo, he’s gay.” And I was just like, that was the level of ...

Cuchna: Wow. Yeah.

Holmes: Even in my personal life, that was the level of homophobia that you were dealing with in terms of Black popular music, where that was all people could talk about. And the reason that Frank drops this letter was that originally it was supposed to be in the album liner notes, but at this time, CDs are getting stolen. There’s listening events, and at this listening event, a bunch of industry insiders are hearing Frank Ocean use pronouns like “he” and as if he’s singing to a man. So he circumvents that.

Cuchna: It’s almost tragic that we have to even bring this part up. Right? To have this letter attached, it’s beautiful and it’s very artful. It’s very Frank, the way that he did it, but it almost seems tragic that he had to do it and now 10 years removed, it doesn’t feel ... I feel like the music in the album has transcended that moment. It’s a really important historical context for the album, but what I think about ... so much has changed in 10 years in terms of acceptance.

Obviously, it’s not perfect and we’re still climbing that hill, but I don’t know. I was reading articles about this moment that we’re looking back on it and a lot of journalists and people that identify as queer, they really respect and remember that moment as a watershed moment.

Listen to the full episode here and check back every Tuesday in August to hear the rest of the season.