Some people follow astrology. Others look for their angel numbers or watch the clock to do things at 11:11 or whatever. For me, at least musically, my spirit guide is the extended musical universe of one Colson Baker, known to most as Machine Gun Kelly or simply (and correctly, according to current brand guidelines) mgk.
It was through my strange obsession with mgk’s output that I unlocked an understanding of everything, really — through him I realized that blink-182 was no longer interesting (he capitalized on the mainstream’s brief mall punk dalliance far better than they could in their state of geriatric self-awareness), Jelly Roll was the funniest celebrity on earth, and, most importantly, that Mod Sun was an important figure to watch.
I’m gonna go ahead and say I’ve written the most words on Mod Sun, at least from within my little world online. I listen to all of his new songs (including the brand new single “Morning Breaks”), I’ve watched all of his YouTube documentaries, I’ve taken sides in his break up with Avril Lavigne.
And yet through my Mod via mgk rabbit hole I found a new favorite obsession — Caldwell. Mod and someone I can’t bring myself to care about named like Yung Crumb or something appeared on his “Flyin’ Pass” remix, and it has ruined myself and some of my friends’ brains for the better part of a year. Keep reading, you’ll see.
Who is Caldwell? He’s fairly mysterious, and before sitting down to write this piece I didn’t know who he was. I’ve since done some frighteningly (even for me) robust sleuthing and now know everything from his full name to his first job to his alma mater to his previous struggle rap project. But because I firmly believe in the cult of Caldwell, I won’t break kayfabe. Your secrets are safe with me. For now.
Instead, I’ll walk you through the publicly available information Caldwell wants you to know about. In addition to his early music, he has noncommittally attempted to launch careers as both a YouTube golf instructor and a Lego vlogger, both of which have approximately one video each. But Caldwell is first and foremost a musical performer.
This self-proclaimed playboy from South Carolina seemingly emerged out of thin air last year, where he immediately went on a tour with Nick Carter through Pennsylvania and Niagara Falls. Speaking with the incredibly fake seeming Starry Mag last year, Caldwell said, “I love performing where there’s genuine excitement from the audience, whether it’s in Canada, Pennsylvania or even North Carolina, a place I’ve come to truly appreciate.” I speak for Canada when I say: we appreciate you too, man.
It’s not just Starry Mag. Caldwell’s press appearances have been sparse, and often seem… generated. But they’ve all got fascinating tidbits. When asked by BSB Fangirls what he knew about the Backstreet Boys before touring with Nick Carter, he said, “I knew they wanted it ‘that way,’ and my Mom loved them…that was about it.” He routinely tells people he idolizes Elvis Presley. In an interview that appears on his Apple Music page, Caldwell reveals his favorite albums of all time are, in order, 3 Doors Down’s The Better Life, Eminem’s The Marshall Mathers LP, and Morgan Wallen’s Dangerous: The Double Album.
And yet my favorite Caldwell interview quote arrives via a chat with “Eden Gold,” lead journalist at “Authority Magazine” — a legitimate seeming publication that just so happens to be hosted on Medium.com. Gold, ever in her journalistic bag, asks Caldwell a hard-hitting question, and he provides a truly incredible answer:
Is there a person in the world, or in the US whom you would love to have a private breakfast or lunch with, and why? He or she might just see this, especially if we tag them. :-)
I think Ted Bundy would make for an interesting candid conversation. I studied psychology and am fascinated by the complexities of the mind, especially for someone whose story has consistently been told by other people. For a live discussion, I’d opt for the Pope and Jordan Belfort, seeking genuine transparency and insight into their perspectives.
Yes, Caldwell’s identity, both literally and metaphorically, is a little all over the place. But his music certainly matches that of someone who looks up to Ted Bundy, The Pope, Jordan Belfort, and 3 Doors Down in equal regard. He’s currently pioneering a “new genre” of music that he sometimes calls “Country Drill” or “Playboy Country.”
And while the press that exists about Caldwell seems to be entirely AI generated, or at least manufactured on some kind of bot farm, there’s still me, born of flesh and blood, loving his music. Yes, if you’re looking for someone to pass the Caldwell captcha test, that’s me. I’m a living, breathing 39-year-old man. I possess a beating heart and an inquiring mind and a troubled soul. And I can easily identify all of the metaphorical images that contain motorbikes while listening to my boy Caldy.
And yet chances are you haven’t heard a lick of his music yet. So without further ado, and with the knowledge that these are the most words that will ever be written about him by a real human being, let’s get into it.
Introducing Caldwell:
Caldwell “Flyin’ Pass” (remix ft. Mod Sun and Yung Pinch)
Jos: The song that started it all. By the time this remix came out in 2024, when everyone from Beyoncé to the drummer from Nü Sensae have cynically gone country, it almost seemed too late. But when I first heard this remix (which ultimately renders the original extraneous and unnecessary), I immediately felt like it was the best thing I’d ever heard. I don’t know how else to say it — to sound like a real country boy, you have to sound straight up stupid, and Caldwell passes with flyin’ colors. Even the title, “Flyin’ Pass” — he’s trying to say “flying past.” Like a plane, flying past.
Living up to the title, there are so many incredibly stupid turns of phrase in this song, and I’m not joking or exaggerating when I say that I’ve thought about them every day for the better part of a year. The pronunciation of “Lamborghini,” the idiotic phrase “And my PJ go,” these just begin to tickle my brain before immersing it in a vat of pure bliss. “I must say, my pretty lady kind of bad as hell.” That’s one of the best lines I’ve ever heard. You’ll soon learn that Caldy likes to refer to pretty ladies. But he’s also hedging here — she’s a pretty lady, but she’s only kinda bad, but also bad as hell. He’s struggling to decide.
And that’s not even one of the best lines of the song, both of which belong to Mod Sun who, in addition to his wonderful adlibs, sings both “She drop it low til the boots touch her ass” and “Sitting first class in my cowboy hat.” I know some of you are keeping track of my supposed irony level on a big bulletin board at home, but I need to just lay it all out there. This is the best song I’ve ever heard in my life, and whenever it ends I can’t wait to listen to it again. If you’re like me and you need more, watch the behind-the-scenes footage.
Sam: I’ve been staring at a blinking cursor in stunned silence for near the entirety of this song’s four minute, ten second run time. Josiah told me he was excited to write about “Caldwell” but I wasn’t prepared for “the Caldwell captcha test.” I wasn’t prepared for the Pope and Jordan Belfort. I’ve known the inside of Josiah’s troubled mind more intimately than anyone should (I’m including Sara) and yet he still finds ways to surprise me with the depth of both his sickness and his ability to be correct. Because this song rocks. The worst part is I know I’ve heard it, yet a quick search of “155” and “flyin pass” or “mod sun” and “caldwell” doesn’t immediately reveal an earlier newsletter where we covered the remix. Did Josiah just send this to me on chat one day? Did I listen to it once and say, like, “lol what the fuck this actually goes” and then forget about it completely? And yet listening to for what is - probably? - the second time I feel like I already know it better than several Jawbreaker songs? I’m out here clicking images of crosswalks.
Caldwell “Beer ’n’ Baddies”
Jos: I wonder if something tripped up Caldwell’s handlers when I was digging too deep into his publishing company and LLC, because the song “Beer ’n’ Baddies” was just straight up deleted from everywhere. Like in the last few days. It’s not a great song, but it initially appeared on streaming in both country and EDM versions, and the music video seemed to blend both mixes into something that was genuinely intriguing, even if you did have to watch Caldwell wander around an incredibly G-rated red cup party that made Degrassi look like Euphoria.
Since the song doesn’t even really exist anymore, it almost wasn’t worth including, but this YouTube Short of a dance video (no doubt some paid attempt at virality) does include my favorite line, which is just picture perfect Caldy: “She love to call me daddy even though I ain’t a daddy, but that’s alright.” Like, that phrase “call me daddy” needed to be explained. Caldwell is so thoughtful and inclusive. That’s why he’s gonna be a star.
Sam: Caldy should do a whole verse where he’s confused by popular slang. “She said no cap but we’ve both got on cowboy hats,” or whatever. “She said she’s feeling demure, but I can’t see the mirror.” “She called it brat summer but she only eats veggie dogs.” Look I’m not the professional here. If Josiah and I ever start a podcast again I think we should tithe a portion of our Patreon earnings to struggle YouTube Shorts creators (shorties?) to make up dances and try to make snippets of our episodes go viral. Just kids crumping to Josiah working his way up to saying “the ISIS home.”
Josiah: MAJOR UPDATE. I stayed up super late on Thursday night because Caldwell said he’s releasing a new song this week. But it’s not a new song — it’s an entirely new version of “Beer ‘n’ Baddies” featuring Sexyy Red. I thought it was going to be a remix, but it’s like an entirely new song. So you’ve still never heard the real “Beer ‘n’ Baddies” but you can hear this version…. Also according to Instagram this was debuted via a Paris Hilton DJ set last night.
Caldwell “Get Out the Way” (ft. Fivio Foreign)
Jos: If you’ve listened to these three songs, congratulations — you’ve heard the entire Caldwell discography. “Get Out the Way” has been previewed and hinted on Caldwell’s sparsely viewed TikTok page for the better part of a year, and it also doesn’t quite live up to the pure ass-bootsin’ magic of “Flyin’ Pass” or the hokey genre play of “Beer ’n’ Baddies” (which, I guess, you’ll never hear in full), it does have some signature Caldy — there are references to pretty ladies and some loose references to general cowboy-ness.
But here the beat is harder, the song more mean-mugging. Caldy was promoting it while attending New York Fashion Week, where he somehow got decked out in head-to-toe Louis Vuitton to attend their runway show, stockpiling a month’s worth of IG photos in the process. (Again, the question of who is funding this and how is kind of the subtext to this entire conversation. Sam, don’t make it the text.)
Curiously, the song features a guest verse from Fivio Foreign, a guy who was famously popping up a lot during the beginning of the end of Kanye’s career. Since then, Fivio did a pro-Trump song with Kodak Black, possibly something in between, and then this.
And yet, even more bizarre, despite its not-insignificant budget, the video for “Get Out the Way” — which was beautifully shot in New York on that same fashion week trip — does not include an appearance from Fivio but instead a “Fivio Foreign Lookalike Contest” where Caldwell attempts to replace the rapper on the shoot.
If you can’t remember what Fivio Foreign looks like, you’re not alone — the casting director seemingly just opens it up to black people, generally, as a series of men and women reduced to their race perform for the camera. It’s transgressive and in-your-face — possibly a critique of DEI in these crazy times — and it doesn’t really work at all.
Since starting my notes for this piece, I saw a TMZ post that made it make sense. The reason they needed a Fivio lookalike is that Fivio Foreign is himself in prison since being arrested on charges of weapons and “uttering terroristic threats.” Too bad he couldn’t find a lookalike for the feds.
Anyway, despite its iffy premise and bizarre execution, the video seems to be doing really well. I mean, all these people signed up for YouTube around the exact same time just to leave a single comment on it.
Sam: Was just letting this play in the background but I clicked over when the song stopped and the weird beeps started, which is evidently the “funny” part of the video with the Fivio Foreign Lookalike Contest. The way the video gets so quiet and shots seem to hang too long to be deliberate has me feeling like we’ve tipped into the unsettling uncanny YouTube valley of James Bridle’s “There is something wrong on the internet.” Like there is no difference between this and one of those AI-generated kids videos where Spiderman stabs Elsa and feeds her to Peppa Pig. I am uneasy.
Ned Paige ‘Flyin’ Pass’ EP
Jos: I’m not kidding when I say Caldwell has changed my life, and I know at this point you believe me. When making 0 Views by SILLY, Caldwell’s music was a guiding light, not musically per se but vibes-wise, and both SILLY drummer Ned Paige and my SILLY essayist/production guide sparkling Caleb became equally enthralled with the concept of boots on asses and cowboy hats in first classes. In fact, whether it was testing my acoustic guitar or working on SILLY remixes for the mixtape and the Fewer Views EP (man I love name dropping my own shit), Ned would always send new Caldwell variations to the group chat. One of them, a 20-minute suite known here as “Flyin’ Pass V,” is a strangely beautiful work.
In fact, there are 5 beautiful works here. It falls under something we are trying to believe in: “all brow,” an appreciation in all forms of music whether the highest of high or the lowest of low brow. There are some hints at brain rot, sure (a recital of Porter Robinson’s cringe monologue about his teeth, a tongue-in-cheek Joan of Arc sample), but this is as pure and sincere as it gets. In addition to Ned’s absurdly obsessive compositions and edits, the EP includes synth and drums by Caleb and acoustic guitar by yours truly. And it’s so good that I had to “release” it on my “label.” And Caleb wrote another amazing essay that you can read on Bandcamp. Thank you for listening. And thank you Caldwell.
By the way I wrote most of this whilst flying on a tiny Air Canada Jazz plane to Nashville. I was in one of the very last rows, surrounded by annoying Ontarions, but the smallness of the plane and the largesse of my Caldwell obsession still had me feeling like I was on a PJ, sitting first class in my cowboy hat. And now I’m typing this from a hotel room at the Nashville airport, where there are constantly airplanes loudly zooming above my head. Flyin’ pass.
Sam: I started to chastise you for visiting the heart of our sworn enemy, but as this EP unspooled I could no longer stay mad at you for your treasonous travel. I guess America can’t be all bad if it’s where Caldwell is. Whatever that album was that everyone who had an mp3 blog 20 years ago was obsessed with over the last while — the one that was only available on a Tripod page or whatever, totally not a gimmick — I listened to one song on YouTube and this is one hundred times better. One time I think I heard a Orville Redenbacher song or whatever the other guy is with the mask — it just sounded like “Wicked Game” but not horny enough? Is that right? — and this is two hundred times better than that. Damning with faint praise? Or praising faintly, damn. Caldwell.