In 1990, when banjo player Alison Brown released her debut album, Simple Pleasures, she had no idea where her career could or would lead. GRAMMY nominations, IBMA Awards, touring and performing with Alison Krauss, Michelle Shocked, the Indigo Girls, Steve Martin, and many more, founding a record label that would become a keystone in roots music – none of these impressive accomplishments were on her horizons, literal or hypothetical. Brown just wanted to play the banjo.

She had recently left her job in investment banking and wanted to give her musical career a legitimate go of it. Tasking herself with intentionally writing an album’s worth of original tunes, over the years from 1988 to the project’s release on Vanguard Records in ‘90, Brown pushed herself sonically, aesthetically, and compositionally. The result was demonstrably spectacular and effortlessly cutting-edge.

Simple Pleasures, which was produced by David “Dawg” Grisman and included Alison Krauss, Mike Marshall, Joe Craven, and more among its cast of collaborators, would help launch Brown’s now decades-long career as a bluegrass and roots music multi-hyphenate and business leader. Simple Pleasures broke the ground, fertilized it deeply, and helped cultivate one of the most innovative and forward-looking careers ever accomplished by a five-string picker.

Now, some 34 years after its original release, that debut album has been reissued – on vinyl and digital, with a handful of digital-exclusive bonus tracks recovered from a cassette tape of demos. The project is a delightful time capsule and a perfect representation of the vast and varied musical ground Brown has covered over the intervening years. She may not have known it then – she readily admits, as a picker in her twenties, she was just taking this “banjo thing” day by day – but Simple Pleasures would lay the groundwork for all of her many successes in the music industry and in bluegrass.

For a special edition of First & Latest, we spoke to Alison Brown by phone about her first release and her latest – which just so happen to be the same album, the original and the new reissue. It’s essential listening for bluegrass, banjo, and roots music fans.

Simple Pleasures was originally released in 1990, 34 years ago. I wanted to start by asking you about your frame of mind now versus then, about what’s changed in the interim. What’s changed regarding how you view yourself as a creator and as a banjo player? Looking back, in retrospect, do you recognize the person you were then? What do you remember about your frame of mind when you first put the album out?

Alison Brown: It was this time in my life during which I was writing this music and then trying to get a record deal; I had just left my investment banking job and had taken this bizarre leap of faith, which I didn’t necessarily get a lot of support for. My parents weren’t saying, “Hey, I think you should quit your investment banking job to play banjo.” [Laughs] It really was a leap of faith.

I just couldn’t stop thinking about the banjo. So, I gave myself the challenge of seeing if I could write an album’s worth of music that would hold up and just try to make a record. And then, in the course of working on that, I wrote these tunes and joined Alison Krauss & Union Station. By the time we recorded the tunes, I’d been in her band for a year. I was really at the beginning of what has become my career path since then, but when I was doing it, I didn’t really know how it would be received or if it would get any props or even if it would be any good. All the validation that came on the heels of releasing this, and then everything since then, has made me a much more confident musician than I was when I wrote the music and recorded the record.

Before this album, were you already writing tunes? Was that something that you always did? Or was this an intentional practice shift for you? Was making an album of your own tunes something you had always been working towards or was it part of that purposeful transition from investment banking to banjo?

That is a really good question. I had never written much music up until that point, but I’d always wanted to. Stuart Duncan and I did a record called Pre-sequel. That was like a teen record, but we had a couple original tunes, stuff like “Possum Gravy on Grandma’s Beard” and “The Great Lasagna Rebellion.” It was like teen stuff.

Anyways, I really had wanted to challenge myself to see if I could write some “real music” – that isn’t really quite the right word, but some more substantial tunes and some tunes that really took the instrument maybe to a new place, which took my voice to a new place. That was a lot of this exercise and those 12 tunes. I didn’t know if I could write them or even if they would be any good, but that was like the beginning of this kind of process of self discovery.

When you look at the credits list – Mike Marshall and David Grisman and Alison Krauss and more – you can see some of the fingerprints of you and your community, but it was a kind of a longer process of you writing and getting to the point of recording, right?

I’m trying to remember… yeah, probably from the time I started writing the tunes was maybe middle of 1988 and then we recorded them beginning in 1990. So yeah, there was definitely some time in there–

Was there some extrapolating in your head of, “What are these songs going to sound like? Who is going to play them?” What do you remember about deciding on how you were going to make the tunes and who was going to make them with you? Because I have a feeling that was just as important a part of the process as having the material to record.

Once the door opened for me to work with David Grisman, to produce the record and play on it, then I was pretty much like, “What do you think, David?” But I knew I wanted to have Alison on the record and I knew I wanted to have Mike, ‘cause I love his music no matter what he’s playing. I’m the head of the “Mike Marshall Plays Guitar Fan Club.” [Laughs] I love his guitar playing. And Mike was in the Bay Area, so that made perfect sense.

But then, in terms of bringing in the flute or percussion, I hadn’t really thought about those things. When I listen to this record now, it’s surprising really how much of a footprint the record created for what we’re doing now. ‘Cause we’ve got a rhythm section and flute in the band. In some ways, it feels like after all this time we’ve come full circle, at least back to the seed that record planted, sonically, for the music.

That’s so interesting, to be able to look back and trace that throughline, when at that point it may have felt like a one-off to have those instruments and those styles represented in the music. And now it’s present through lots of your work.

Yeah, it is really interesting. There’s obviously things that weren’t included [on Simple Pleasures]. We’ve had piano in the band pretty much since the beginning and we didn’t have piano on that record, obviously. But I don’t know, somehow that doesn’t seem as much of a template thing, the idea of percussion elements and certainly the flute. David really brought that – and the idea of incorporating cello. I’m not sure I was really thinking about those things. My thinking was probably more in the bluegrass-rooted box.

One of the things that’s definitely changed from the original Simple Pleasures to the reissue over those 30-some years is these bonus tracks that you’ve added – such a time capsule. I wanted to ask you about their… I want to say provenance, but I don’t mean to be that formal. Like, how did you hold onto the demos over time, did you always have them in your back pocket?

You know, as we were working on re-master I kept thinking I knew I had a cassette of the demos. I just dug around and I found it! That’s where the actual takes came from, but that between-take talking, to me, is my favorite part of the whole thing. Just hearing Mike and David and Richard Greene, who produced those demos, talking to each other – I just think that’s the coolest thing. That came off the 2-inch tapes that we had. But the 2-inch tapes, we didn’t have the final mixes of the demos. So, it just worked out that we dumped the cassette tapes into this computer and tried to sweeten it a little bit and that’s what we used.

Looking back, this was a big transition point for you with a GRAMMY nomination, winning IBMA Banjo Player of the Year as the first woman to win an instrumental award. Of course this would end up a seminal album and was a really important kickstart for your incredible career. But at that point, back in 1990, were you worried about it? What was your frame of mind as far as expectations for what this album could do and where it could go?

I’m sure that I had no expectations. [Laughs] It was just something that I really wanted to do myself. I wanted to see, could I write a bunch of music and would it stick together? And, can I get some great people to play on it? I was just happy that all those things came together and I got it on a label.

It was just so cool to be on Vanguard Records. The Welk Music Group had bought that catalog and they had just started signing artists. I was one of the first artists they signed to the Vanguard imprint. All that was enough, but then to get a GRAMMY nomination was completely a surprise. I didn’t expect that at all, or the IBMA recognition. That validation was huge, obviously, and it would be for anybody, but for me it was just so huge. I actually took my parents with me to Radio City Music hall for the GRAMMYs and that went a long way toward them accepting my career 180. [Laughs]

It seems like this was definitely proof of concept for, “I can do this banjo thing. I can make banjo records. I can do this as a career.”

And in retrospect, I completely agree. In the moment, none of those things [were certain]. That’s what they say, “Hindsight’s 20/20.” And that’s so true; when you’re in the moment, you just don’t know how it’s going to turn out. Then it turned out great! I feel so lucky every day that I get to play music or create music or help somebody else create music, all that is just such a gift. Because it was not a foregone conclusion, I could easily have gone back to investment banking or something else with my tail between my legs. I’m just so grateful that isn’t the case.

At this point in your career, people think of you as a multi-hyphenate, as somebody who runs a label, is so active in the industry, and picks a really mean banjo. But this project predated Compass Records by several years. Were you already planning that sort of multi-prong, multi-hyphenate approach then? Or do you think it would be a surprise to 1990 Simple Pleasures Alison that you are the multi-hyphenate you are now?

Yeah no, I did not know it was [in my future], I think I was really just taking it a step at a time. At that particular point in time, my goal was just to write tunes and play in Alison [Krauss’] band. Then, when I left her band, I was really at this juncture again. My parents kept saying, “We really think you’d enjoy going to law school!” I was on the edge of applying to Vanderbilt Law School when I got a call from Michelle Shocked looking for a band leader for her world tour in 1992.

So no, I definitely didn’t have the multi-hyphenate, as you put it, plot hatched at all yet. That’s really something that came during that time that I spent with Michelle and then Garry West, who was playing bass in the band [with her as well]. We connected on a personal level, on a business level, and we started talking about “the good life.” Like, how do you make a life out of music? That’s when we started envisioning the different spokes of the wheel, and one of them was a record label and one of them was playing banjo and touring. That 1990s Alison was really just taking in a day at a time.

There’s this quality that musicians talk about a lot, almost to trope-ish levels, of not liking listening to themselves, not liking going back and hearing their own musical ideas or their own creativity from the past. It can be cringey! When you hear your young adult voice on the banjo now, what’s your reaction? Do you bristle at it? Do you feel inspired by it or do you have a moment where you’re like, “I can’t believe that I played that or I did that”? You’ve been inhabiting these tunes to remix and re-master them, not just rubber stamping a reissue. What does that feel like, to be going back and forth between who you are now and who you were then?

I really thought it was going to be like a lot of cringey stuff, like listening to those tracks and thinking, “Oh god, why did I play that?” Instead, I had a completely different feeling, because I felt like I could hear and really remember both the joy of figuring out that I could do this thing and the uncertainty of, “I don’t know if it’s any good or if it’s going to connect with anybody at all.” I can hear both of those things, but at the end of the day, what I felt most was just wishing I could reach back in time and give myself a pat on the back [and say,] “It’s going to work out okay and you’re on the right path.”

Because I think that’s the thing, we’re all looking for our true path. Sometimes it’s really hard to see, and for me, it was definitely hard to see. I really thought that I would be like a respectable business person and instead – well, I hope I’m a respectable business person, but it’s certainly not what I expected to be! [Laughs] I really thought, banker, lawyer, doctor, that kind of thing.

Your portfolio as a banjo player, label head, and producer is so diverse. And I wondered if you feel that’s directly correlated to being a woman who plays the banjo, or if you think there’s something else that’s driven that or informed that? Because I firmly believe marginalized folks in roots music – really anyone who’s not a straight white man – we often have to have very diverse career paths just to make a living, to make ends meet.

One thing I do notice is that big opportunities that opened up for me early on, they were all created for me by other women. That’s really not lost on me – whether it was Alison Krauss or Michelle Shocked. It wasn’t a male band leaders inviting me in. I think that’s really significant and that’s one of the things that I think is interesting about the times we’re in now, the fact that there’s much more diversity – even though it’s not as much as we would like to see. But there are women peppered throughout the ecosystem of the bluegrass community. We’re really in a position to empower and bring up the next generation, where we weren’t so much before. That makes it a really exciting time. I know that’s something that I love to look for opportunities to do.

If I’m producing a record, I want to bring those other voices into the room and let’s raise the next generation. ‘Cause when you come out of investment banking, you can see how adept the guys are at bringing on the next generation of guys, but women in corporate situations just historically haven’t [had the same access]. There are many reasons, it’s not their shortcoming. I think it’s just the circumstances, but now it doesn’t have to be that way. I find that particularly exciting.

34 years later, these folks who played on Simple Pleasures are still part of your community and are collaborators of yours. Back then, were you thinking, “All right, these are my ride or dies! We’re going to go the distance together.” Or was it like, “I can’t believe I get to be in a room with these folks and I hope we can do it again”? How does it feel now to look back and have decades-long relationships with these folks that you made the album with and to have that community be such a present part of the music that you continue to make and the records that you put out?

It’s amazing to look back and to think about the fact that I’ve known Mike Marshall since, gosh, I think I was a teenager the first time I met Mike? To have 50-year-long relationships with some of these people, it’s an amazing thing and it’s such a gift. I think one of the best things about our community is that people can have careers that extend over decades and you can have friendships with people that extend over half a century or more. I’ve known Stuart Duncan since he was 10, so I’ve known him for half a century. It’s crazy and wonderful too. And it’s such an amazing aspect of our community.

I don’t know if it’s the same in other kinds of music, but I think the intergenerational aspect of bluegrass music and roots music just creates for some amazing lifelong friendships. I think it’s not uncommon for people to start when they’re 10 years old – or, Stuart started playing this music when he was six or seven. When I met him when he was 10, he was already a hotshot fiddle player. The fact that you can get into this music as such a youngster, keep playing it, and there’s room for you even when every hair on your head is gray, it’s just a great thing. I think in popular music the window is more narrow.

But in this music, people want to see you play your music whether you’re six or whatever age. How old was Bobby Osborne? He was 92! The record that I did with Bobby, Original, we was 86/87-years-old when we recorded that record. You wouldn’t see an 87-year-old pop artist probably making a record.