TuneDig is an in-depth and informed conversation between two lifelong friends about the power of music — one album at a time.

In each episode, we go down the rabbit hole to spend a while in the strange world we discover. We take an honest look at creativity in all its complexity—from writing and production to history and cultural impact.

We promise you’ll learn something new every time, no matter how much you already love the album we explore.

Episode 010

The College Dropout

Kanye West

The Kanyepalooza™ of 2018 made us question if Ye ever actually made anything that made him worth all this fuss. (SPOILER: He did.) This investigation wasn’t as simple as missing the old Kanye — because every Ye fan seems to have a different favorite album — but we wound up looking back with admiration on the first time Donda’s son held the zeitgeist in his hands and turned it upside-down.


Episode 010: Kanye West's "The College Dropout": Audio automatically transcribed by Sonix

Episode 010: Kanye West's "The College Dropout": this mp3 audio file was automatically transcribed by Sonix with the best speech-to-text algorithms. This transcript may contain errors.

You're listening to TuneDig, a podcast for music lovers. The premise is simple: in each episode, we dig deep into an album we love and then we give away a copy to you of that album on vinyl. Go to TuneDig.com To see what's up for grabs and learn more about us.

Today we're talking about Kanye West's "The College Dropout".

I want to start this episode by saying I was really not looking forward to having this conversation before we dug in the Kanye West conversation.

Right. Every parent dreads a sit down. I need to talk to you about something serious.

This is the first episode that really makes me appreciate this podcast to the extent that I think I fully can, because time and memory had convinced me that I probably wasn't ever that big a Kanye fan and nothing that he had done was really that big a deal.

So I feel like I'm almost reclaiming my own narrative around kind of just by doing this. So thank you.

I love that this is the least contentious, brilliant Kanye moment. The awareness of his own greatness was coming out at the same time in this record as the self awareness of not thinking too highly of himself, of cautioning other people about the need to aliev themselves. And then conversely, almost in the same song a lot of the time, trying to convince people to think more highly of themselves.

I love that you talk about the different layers of awareness, and that seems to be the thing that has maybe been lost over the years. There's a biting sense of humor on this record. The subject matter was heavy, but he wrapped it in this like dark comedy thing. There was like a sitcom delivery. And the longer that I listen to it, the more that it felt like s part to me.

There are a lot of people out there making up rumors about me that are malicious and untrue. But I'm going to prove once and for all I am not a fish because I am a genius and ascertain it skewered everything.

It skewered rich people and himself and materialism and all thirty two of those skits or whatever. But he kind of goes everywhere, right.

Like no stone is left unturned and there's just such an energy and such an intensity. It's like he's doing 20 years worth of homework and turning it around all at once. It's it's unbelievable and exhausting, but it's all really razor-sharp.

This thing was recorded, produced over the period of four years, produced mostly by Kanye himself, even though officially he recorded at the record plant in L.A. Most of the production was in his own apartment or whatever he was, he would walk around carrying a Louis Vuitton backpack filled with old discs and demos and just take them back and forth to the studio. One of the quotes said he he crafted this production 15 minutes at a time. The record leaked months before release, and he used the feedback from the leak to do more production work before the album itself got released.

Again, that's what was weird about people thinking it was so crazy when he was swapping out versions on streaming of the Life of Pablo. It's like, guys, he's been doing this the whole time. He's never married to. This is exactly what this piece of work is. It's weird to use the word like Egoless to describe Kanye West ever, but that he is egoless enough to say this art is not static. It needs to change. It needs to interact with the world. It's in a given moment. It's like that is genius. That is a next level way to view your art. And that he's been doing that since he was very young and hungry is incredible.

Tony Williams, he's saying on spaceship, he said, I remember asking Connie if I could do something on the album. And basically he was the response was in Konneh style. I love that people can say in Konneh style because it always precedes a statement like this. Yeah, everybody wants to be on the album and that that was his way of telling him that, you know, you're probably not going to get on this particular album. But then he picked up Connew from the airport after that, not long before the deadline for the album. Like two weeks before it, Kanye played spaceship in the car on his way back and Tony started harmonizing with it, which. Mean says. This county went, oh, I want you to do that on the record, and they brought him right there, like immediately brought him into the studio to record the harmony part for that song. That's amazing. I think that approach made everything feel so full and fresh in a way that's just hard to describe.

Kanye has had such a good marketing mind for so long, and he just has such an advertiser's sensibility of how to make it clever and digestible and repeatable.

But he can also be really profound.

All Falls Down is one of those ones that every three or four bars are just like, oh, oh my God, the idea of Louis Vuitton backpack full of tapes full of ideas like just feels like it starts to work. Like he's like you're in the room with with Morty's mind blower's and you're just like shoving anyone in your head over and over again.

And then you go, oh, those two go together. The police that Sade's you know, and we buy our way out of jail but we can't buy freedom. We have a lot of clothes, but we don't really need them for things we buy to come up. What it that they made is paid out self-love they wealth just so it kind of set up on the drug dealer back on crack hip crack and a white man get paid all but I think that he could pack so much that was thought provoking into a single line.

You know, he did three or four bars and there's guy again, the white man get paid off all of that. And to be a white kid in the suburbs that had never really thought about the systems that allowed things like that to happen. And he did it in kind of a toss off line or he was like, well, yeah, I mean, I've known this my whole life. Like, this is common knowledge where I come from.

It was a real deceptive Trojan horse, the way you think about a huge thing, because he wasn't beating you over the head with it.

There was sort of a flippant and his delivery was so cool and it was so first person POV. And that's a thread that goes through. A lot of the record for me is like you just see him as this person. That's really interesting and you want to know more about him. And so when he says things like that about injustices or things that are happening to him or that he's witnessing, you're like, oh, yeah, man, that's messed up.

You take a great hook. Those lines that you're pointing out, it flows all the way through that video where you are experiencing so much of that stuff. And like, it just feels like it works together. Like I remember feeling like that music video felt like it belonged with the song. And that's such a rare feeling for video, like it takes such vision for somebody to be able to have a thread that can go through everything like that. And that's just one song. Yeah, right.

And the other thing that struck me when I was listening through the record the other day in preparation for this was there are twenty, twenty one tracks on this. And yeah, a lot of them are skits, but every third song or so is a massive career making song and there are no less than half a dozen of them on this record.

All falls down and Jesus walks and spaceship and workout plan and slow jams and school spirit, they're all very different. They all cover different subject matter. They all have a different sound, but they all have that kind of a voice. They all have that kind of a cadence and they all swing for the fences. You know, it's any of those songs would have been huge for one artist for for a number of artists and that they're all on one record and all on his first big record. You're just like, good God, this guy had a lot in the tank.

You can't overemphasize how masterful this whole thing was hit after hit. He's obviously doing all the verses himself. He's doing all the production himself. But then inside of that, inside of crank it out, an entire album worth of hits, he's doing two completely new things at one time. That's hard to appreciate. In hindsight, he had trouble getting a record label to release this stuff because his approach to hip hop was culturally different than everything else that was being signed hip hop at the time. Right. He said maybe I should have been wearing a basketball jersey. I think the hilarious thing about it for people like us at this time is when you go back to try to understand what do you call the phase of hip hop before Kanye West changed the face of hip hop. And it's called gangsta rap.

But it's weird because, like, was it, though, it was big time when I think about the thing that came before Kanye being conscientious in calling out materialism, I always think of stuff like no limit and cash money and stuff with the pen and.

Artwork, and it was just about opulence. It was just about materialism, like it wasn't sure they talked about street stuff.

But I think about the song no one's done as being like the antithesis of a Kanye for or thing.

Maybe we want to call me, which happened out the platinum platinum brim with the platinum pink and the platinum chain with the platinum y and the platinum right to the point that had to happen to allow Kanye to kind of windfall in behind that, Kanye was the response to that thing, but that all of that was kind of lumped in as gangsta rap just showed how worlds apart we were, which is weird because it wasn't that long ago. But when you look back on this stuff, it feels like a generation ago.

I guess the irony here is like you're going to have Drake unless Kanye had started this, right? Absolutely. So thanks. So not only is he struggling to change hip hop in a way that allows room for introspection and self awareness, he's also simultaneously creating a new production style chipmunk soul is the actual phrase that would come to refer to an entirely new production style that he did, taking old soul samples and speeding them up and in changing the vocal register and all that stuff to make hooks out of it than he has always been a master of sampling.

He wasn't the first to do it. That, in a lot of ways, obviously was like a sample of hip hop the whole time.

It started getting interesting, I think, with Juicy J as a producer that started coming into their own with soul samples, but like he was the first one to build a whole orchestral world around it. And that was really the differentiator was he he built a sound around it rather than placing it in as an element. But it was also used as kind of like a humorous tool to me, the peak chipmunk soul thing for kind of slow jams.

They said this guy gets away with it, right, like it was used to really almost farcical effect and everything about that song is so funny because it's so meta, right? He basically writes like a sarcastic boner jam to the degree that like he got Jamie Fox on it. And I love I read a retrospective of critics reviewing their reviews of College Dropout 10 years later. That was my favorite article that I read about this whole thing.

One person remarked that even the way that he used his guest seemed provocative, like there was even a statement in that so that he used Jamie Fox on that song, this sort of like funny guy that was starting to get into serious RB career and literally sang Al Green like he just sing the names of RB singers instead of any moves that those people would have done is so like is such a middle finger to me is such a good microcosm of the whole college dropout experience. Assessing himself for windsurfing.

Before I forget, speaking of reviewers reviewing their reviews way later, one of my favorite things and when I say favorite, one of the things I hate most about the Internet is Pitchfork's undying just worship of Kanye. Even this original record like launched that ridiculous love affair between them, where they called this flawed, overlong, hypocritical, egotistical and altogether terrific things. Pitchfork And ever since then, every album has been like that.

A similar thing happened with Rolling Stone, John Caramanica. I don't know how to pronounce his name, but he's a great music writer and he wrote the College Dropout Review for Rolling Stone and they gave it three and a half stars. And he said in this retrospective, basically, like, yeah, that was the best that was the best rating that we could give it at the time because it was Rolling Stone. And if it wasn't like the biggest rap album in the world, they just weren't going to do that. He stopped just short of being like, yeah, Rolling Stones racist. And if you're not Bruce Springsteen, you're not going to get five stars, Bruce Springsteen or U2. And now it's the same thing with the Rolling Stone. They love him because he's entered this like Bono, like Zygi, sort of larger than life thing. But back then, they were like, nah, he's just a regular black dude doing an art form that we don't like. Well, is hip hop in the Rock and Roll Hall of Fame, even though our entire art form that we base is magazine on is like based on bastardizing black music.

There are some other really good tidbits from that retrospective.

John Caramanica said he seemed really important at the time, not just for being a good producer. There are plenty of good producers, but for being a producer that changed the sound of radio and of artists who are more established than him. So you talked about him having a very fully established sound. Obviously, he was a very significant figure in evolving how Jay-Z was presented to the world. And you have to admire someone who has enough chutzpah and enough vision and confidence in his vision to not just be a guy alone in a room, starting an idea, but going into the room with far more successful people and having them buy his idea. He has had such an outsized influence, partly because of that self belief, but largely because he delivered on that self believe. He knew he was on to something and he delivered it in spades here.

And I hear so much in this record that was like it had never been done to that point. But it's been done since of times since then. And I didn't realize how much of popular culture was steeped in this stuff. He created a whole new vocabulary.

If you're going to be that outrageously almost egomaniacal, there are two choices you can either deliver, which Kanye did and almost no one ever does, or you recede back into the ether and no one notices you and they just say, well, that I was full of himself and wasn't good. It's kind of a totally different approach than someone like me would take who was thought to be super conservative and build things up over time. Right. It's been 15 years networking to get the right opportunity seized on the right moment. Don't screw that up. Take that one network more like and, you know, build that up towards some eventual thing. Or it seems like, you know, I feel like I have enough to go on. So why don't I try this? And eventually someone will let me released an album and I don't know, I'll get 10 Grammy nominations on my first one, including best hip hop song, best rap album. There are so many concentric circles of that concept on all of these songs. You've kind of touched on it when you get to Jesus walks, that thing that everybody loves. Not only does it have outrageously good production, the song itself is great. His delivery is great.

Oh oh oh oh oh oh most. Oh we have.

So no way because could get that part not far into the song where he takes a deep breath when he's delivering, trying to catch on. So what it takes to get all of that stuff is so well done. And then inside of the song he's talking about, if he ever writes a song about what this song is about, that'll never get played. And it ends up being the best hip hop song of the year. Right. The further away you get from stuff like that, you have to it's almost like you become less certain about what he thought about when he was saying it, because it's almost like the first time you hear it, you go, oh, look at him. He got famous and he didn't expect it. Not long after that you go, that is definitely not the case. He totally expected to get famous. It's like the further away you get from it, kind of the more in depth it becomes.

Yeah. You talked earlier about the ethos of working until it reflected the profundity and the brilliance of of what he knew. The core idea of the thing was he wasn't going to settle until it really got all the way there. And Jesus Walks is to me, the best example of that on this record, not the song, but the video. So there's two versions of this video out there. Right? The first one is pretty straightforward in its narrative. The song is about reclaiming the narrative of who are Jesus?

Children, strippers, hustlers, drug dealers, Jesus walks with them. But the first version of the video is things happening in the streets on the south side of Chicago. And he's a preacher. And, you know, there are some tropes. There are some cliches. It waters down the message of the song a little bit almost because it feels like something you've seen before or something you've heard.

And you're like, all right, well, this is conscious rap, whatever, I get it. But it goes back into the second version of this video that's even higher budget and has a cinematic quality to it. Like a lot of it has a film grain to it. And it's this incredible high concept video where in addition to this great performance that he turns in, in front of the green screen with the flames behind in some of the shots and then in the close up, there's a halo light over him. Right. So that great dichotomy and a really beautiful, subtle way. But then there's this thing happening with the prison chain gang and this very visual 13th Amendment prison as slavery motif that's happening where the chain gang goes and cuts down this tree. That then becomes a cross that a Klansman carries that then lights on fire. That then even in the last shot of the video, he the Klansman is also on fire and he drops the cross and it lands upside down. All that happens and it looks like a mini film. And he got to the point where he was doing really opulent, blown out stuff kind of on the regular, you know, runaway. It was kind of the logical end point of that later. But there was nothing happening like that, like that's Criterion collection type stuff. So he knew there was a beautiful, powerful, transcendent message in the song and he knew that he was too literal with it when he did it the first time in a video so that he went back to the drawing board, had that video pulled from everywhere and came back and said, no, this is important. I need to treat this like Seventh SEAL or Federico Fellini or like this needs to be timeless. My life is dope and I do dope shit.

And this is when everyone knew it was going to start and we were watching sketches we like we could watch some sketches. No one's ever seen these before. We show like the Rick James sketch and all these great sketches and in the middle of it. Phone rings And he's like, Hello?

No, no, I can't.

No, I know because I'm at the edit for the day Chappelle's Show watching sketches that no one's seen before, and then it goes like this because my life is dope and I do dope.

I mean, he was willing to put it all on the line for a message like that and that early in your career of all times to be like, no, I will not settle. I am going to take a risk. Like there was something so maverick and so badass about that. That's the thing that I had totally forgotten. But that whole part of this narrative alone will make me defend Kanye until the end of my days, because that is worth it. Like that is the reason that we keep making music and art, because it can get to that place that you you got to dig a little deeper for you got to fight a little harder for it because you know, it's there. And if you're somebody with as big a vision as Kanye, you can't stop until it's realized.

And there's the thing again, where he's not afraid to say, the first time I did this, it wasn't good enough. I'm going to do it again. Very iterative. There is the thickest layer of irony and we know it, that the person who was teaching us about not tying ourselves too much to our first attempt is Kanye. But that's OK. That's why it's so great to be able to reach in and take stuff from this record. He would continue to perpetuate that idea of like, if it's not good enough, the first time, even if other people think it's great the first time, if I don't think it's good enough, I'll just do it again. Right. There's nothing wrong with having two versions of updating it. Version one point, one final.

There's something to love so much about. He's clearly not interested in the race for second place. Like he doesn't want to be the best one. He wants to be the only one.

The big hairy American wind machine.

For your laugh, you know, we'll talk about that for trademark, Rick, about why he wants to be in the rarified air category of a Beatles or or an Apple.

You know, these ridiculous comparisons he makes later in these interviews to comparing himself to Steve Jobs and great architects and whatever the ambitions are clearly laid out on this record that he wants to be set apart. Hip hop is just simply because he's a dude from the south side of Chicago. Right. But he wants to do grandly ambitious, world changing stuff. And that's why almost 15 years on this, in retrospect, is clearly a watershed. Hip hop record like this belongs in the pantheon with the Illmatic and the life after deaths and the all of those records. And it's so different from all of the other records that you would put in the canon of great hip hop. And that's all the more reason to include it.

Yes, it's almost hard to think of a of a modern example of how good he was at recognizing opportunities to dig in and be great, even remembering back for this record. The thing that hooked me was still through the wire, which is sure that's how a lot of people were definitely exposed to it. Right. But like that that idea, this guy is in a near fatal car crash, late 20s, and then sees that as an opportunity to channel something different in something media into creating the music to the point where you can record verses with your mouth wired shut and it somehow doesn't come across. Gimmicky was a thing that blew my high school brain apart. I really opened my mouth, wired shut down. Right now, this is I got to say now there's so few examples of being able to be earnest and timely at the same time and have it executed so well, he talks about the album being his medicine and he's working through this song. He released that song originally on a mixtape in thousand two when he announced that he was recording this album that would be released later. And he talked about that the theme of this album was to just make your own decisions and don't let society tell you that this is what you have to do.

And those sound like such platitudes, like we were even watching him give interviews beforehand that seem like maybe he hasn't really practiced saying the things he wants to say because they just seem like inspirational posters said by somebody who was really trying to make the pop collar thing happen for a minute. But the fact that that person, whoever it was, could record through the wire and have that just gut come across in the song itself was nuts. And then just to layer that on top of all that crazy production, I mean, to sample Chaka Khan in that song along with all the other great samples that are happening on the record. The other thing I just thought was cool kind of trivia to mention, because you mentioned school spirit, in order to get Aretha's permission to sample her in that song, he had to edit out any curse words, including in the unedited version of No. If you listen, there's no unedited version of school spirit because she made him not have any curse words that I never noticed.

All right. Here with a man, she really was the best. She was too real.

We have spent this whole time talking about Kania walking into a room and telling everybody else what's up? And Aretha is like, no, you will wash your mouth out with soap.

Yes, ma'am. Absolutely. You're right. You are so right. Thank you for the opportunity to be here with you today. Like, it really is an honor.

Let me think about Connie's willingness to relate to that weird request just to get her sample on a song like that's so great.

You know what that is, though? That's because, I mean, this truly is a high compliment. Cunio I was a mama's boy. Kanye was raised by an incredible woman who is a strong presence in his life. And, you know, a lot of what we talked about probably is at least loosely correlated to losing his mom, not changing his Headspaces pretty irrevocably.

But Aretha is a powerful woman, much like his mom was smart and in control and so irreplaceable that I think he just recognized something that he knew he needed to respect.

That's a great story, man.

The sax performance on Last Call, that really kind of weird long song that eventually devolves into something trippy at the very end of the album. That sex performance was from Keith Anderson, who played with Prince.

No, I they pick that to be I was thinking I. Go do some more work. But she just one popping off like that. I was staying in Chicago, I had my own apartment. I'll be doing like these four local acts just to try to keep the lights on. I'm going to go out and get it off layaway, get some joy to some Logitech, the Marine I really love.

I think I may just want to be. So there's just like so much greatness, just like all over all these different parts, not just in the samples, but in the influences in people like Mos Def showing up like all kinds of stuff like that, just so rich.

Hopefully one day everyone will.

But everyone should own a copy of this record like Purple Rain, this record is capital, I am for that. And then he graduated I college degree can still get that Rockefeller.

Go to TuneDig.com to sign up for our emails and click the link in the email when you want to win. That's it.

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Let’s be clear: "Bitches Brew" is a challenging record, even to some of the best musicians in the world — but all of them say it’s worth the investment. It’s the kind of trip that, even if we *could* draw a map, it wouldn’t take you there. Let go of the need for meaning and enjoy the ride with us. We can promise you’ll be pleasantly surprised where you end up.

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TuneDig Episode 40: Fiona Apple’s “Tidal”

On the heels of one of 2020's most acclaimed albums — Fiona Apple’s Fetch the Bolt Cutters — we revisited Apple’s debut Tidal and wound up working to extract ourselves from the mostly male gazes that made its reception … much different. We arrive at a question much like writer Jenn Pelly had: “People would constantly prod Fiona on how an 18-year-old could write songs as mature as these ... Why did they not ask instead how she became a genius?”

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TuneDig Episode 39: Death Grips’s “The Money Store”

The modern world is accelerating beyond our control, shaping our reality in ways we can’t yet perceive or understand. Enter Death Grips, an art project capturing the chaotic energy and illustrating the absurdity of our hubris in trying to harmonize the surreal and extremely real — never more perfectly than on 2012’s prescient "The Money Store".

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TuneDig Episode 38: Augustus Pablo’s “King Tubbys Meets Rockers Uptown”

Reggae music is easy to take for granted, but its impact is underappreciated and massive — in the case of dub in particular, everyone from Radiohead to Johnny Rotten to Run-DMC owes it a debt. Augustus Pablo and King Tubby together created what’s regarded as “one of the finest examples of dub ever recorded.” Join us as we dive into the culture, history, and unique engineering experiments that made it possible.

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TuneDig Episode 37: Rihanna’s “ANTI”

By every measure — sales, awards, chart-toppers, global name recognition — Rihanna is objectively as big as the Beatles ever were. In fact, ANTI is so big it’s still on the charts, a record five full years later. Take a closer look with us at “the record you make when you don’t need to sell records”, and get a taste of the true freedom that comes from focusing on your inner voice when faced with insurmountable expectations.

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TuneDig Episode 36: Son House’s “Father of Folk Blues”

All American music traces back to the blues, and deep at the root sits Son House. That the recordings on "Father of Folk Blues" even exist is something of a gray area that cuts to the heart of the great American myth, but wherever you land after hearing these stories, you’ll find that what matters most is what the great Muddy Waters once said of House: “That man was the king.”

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TuneDig Episode 35: Melvins’s “Stoner Witch”

The futility of describing the Melvins has stretched critics in the direction of absurd words like “Dadaist” for nearly 40 years now. They’ve belligerently flogged any attempt to pinpoint their essence simply by being themselves, but "Stoner Witch" remains a reliable mall directory for the Melvins’ vast and wild discography. Grab yourself some pretzel bites.

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TuneDig Episode 34: Dolly Parton’s “Jolene”

We should talk about Dolly the way we talk about Prince. Her extraordinary kindness and unique kitsch both make her universally loved, but what gets left out of the conversation is the very thing that made her famous: the music. Join in as we focus attention on the sonics and songwriting of the low-key masterpiece "Jolene".

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Kyle and Cliff

BONUS TRACK: How We Got Here

We got a bunch of interesting listener feedback in our off-season, and it encouraged us to shed some light on why we do things the way we do ‘em. Also, we reflect on our first writeup, which was ... interesting.

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We're Cliff (right) and Kyle (left). We’re two dudes born and raised in ATL with day jobs in tech and sustainability, respectively.

We met in middle school, and in one way or another, music’s been the thing that’s kept us close for the two decades since — whether it’s sharing and talking about new music (like this podcast, except in our texts or over beers), going to shows, or working with our favorite record stores to help them survive and thrive.

We started TuneDig as a little art project that connects us more deeply ourselves and to the world through the infinite gift of music. We hope you’ll join us for the conversations, let us know what you think, and share discoveries of your own.

More About TuneDig

TuneDig began as a little something called MusicGrid.me, which we created after realizing there was no place online to directly exchange music recommendations with your friends. Our aim was simple: to make rating albums simple, useful, and social. We got some love from places like MashableWiredEvolver.fm, and Hypebot. We managed to foster conversation between music lovers, get thousands of reviews, and meet great people.

Along the way, we realized that record stores were an essential part of the music lovers’ community. After many a conversation about how we could helpfully connect them to the people who loved them, we began helping them leverage technology to create new revenue streams and embrace streaming services without giving up what’s unique to them: expertise and curation. (Long live the counter clerk who knows exactly which record will be the right introduction to jazz fusion!)

TuneDig is our vision to connect music lovers with the music they love, because no matter how much has changed in the way we discover and enjoy music, recommendations from people you trust and respect will always be the best way to find new music you’ll dig. With this podcast, we’re channeling the spirit of trusted curation pioneered by record stores, and bringing you something to take you deeper into music you can love.