Podcast: Interview with Jazz Guitarist Sheryl Bailey

by | Aug 29, 2023 | Interviews, Podcasts | 1 comment

On today’s podcast, Greg and Vin interview one of jazz guitar’s leading players and educators, Sheryl Bailey.

Here are the key highlights from the interview:

  • Sheryl started playing guitar at age 13, inspired by hearing jazz greats like Sonny Rollins and Charlie Parker on the radio. She studied at Duquesne University and Berklee College of Music.
  • Sheryl discussed her experience taking a lesson from Emily Remler, calling it a positive and formative experience.
  • As a teacher, Sheryl stresses fundamentals like rhythm guitar, reading music, scales, chord voicings, and learning tunes. Developing good practice habits is critical.
  • For improvisation, she compares learning jazz language to learning French – it takes deep immersion, listening, study. Your voice emerges through the tradition.
  • Sheryl shared advice on preparing for jam sessions – learn the common tunes, observe the vibe, build relationships. Don’t compare yourself to others.
  • She released a recent album on vinyl, available digitally.

Audio Version:

Join FretDojo’s online jazz guitar academy here


Resources And Links Mentioned:

YouTube series of “Homage”:
Sheryl Bailey and the SBQ: “Homage” YouTube plalist

Truefire Artist Channel:
Sheryl’s Truefire Artist Channel

Webpage: Digital downloads, merch:



Greg: Hello and welcome. My name’s Greg O’Rourke. I’m the lead instructor fretdojo.com. I also have with me on the call today my fabulous assistant instructor, Vin Amorando, and today we have a very special guest for you on this podcast.  Sheryl Bailey, or, as in Australia, apparently she’s been named ‘Bales’ as a nickname by my Australian colleagues.

Sheryl has been described as “One of the top players in an emerging generation of jazz guitarists” by Vintage Guitar Magazine, “Among the best bop guitar players” by Just Jazz Guitar. And “One of the new greats of her chosen instrument” by Philip Booth of Downbeat Magazine. Sheryl got her start on the guitar at age 13, attended Berklee College of Music from which she holds a Bachelor’s of Music degree.

She won third place in the Thelonious Monk International Jazz Guitar Competition in 1995 and was chosen by the US State Department as a Jazz Ambassador. For a South American tour in year 2000. Sheryl has nine CDs out under her name and has played with a who’s who of modern jazz guitar greats, such as Frank Vignola, Howard Alden, Kim Plainfield, and many, many more.

Well, I feel like there’s so many credits here. Maybe we’ll have to do an edit here Vin, I don’t know. But… I think we…

Vin: well, I actually crunched this down (laughs).

Greg: You crunched this down. Wow. This is intense. Sheryl is also one of the leading jazz guitar instructors in the space today.

She’s a professor and assistant chair of the guitar department at Berklee College of Music, where Vin studied as well, and a professor at the Collective in New York. , Sheryl’s the author of the book, movable Shapes Concepts for Re Harmonizing Two Five published by Mel Bay, as well as several top selling video courses on platforms such as TrueFire Jam Play, Mike’s Masterclasses, and others.

Phew. So needless to say, we feel privileged and thrilled to have her with us today. So welcome very much to the Fret Dojo podcast Sheryl Bailey.

Sheryl: Hey, thank you guys. I need to update that bio because actually my 12th release just came out this summer.

Greg: Oh, there you go.

Sheryl: And actually the Organ Trio is starting our 21st year together as a band. So that’s note to self to update my bio.

Greg: Fantastic. Ok Sheryl well, maybe what we’ll do is we’re going to start at the beginning. So do you wanna, sort of ,for the audience, tell a bit about yourself. You know, how you got started with guitar, but particularly with jazz guitar.

Sheryl: Well, I actually came from a family of professional musicians and actually it was all the women who were church organists and phenomenal musicians.

And the funny thing is, when we were all kids, I was the youngest and my brother and my sisters, we all had to take piano lessons and I was a horrible student. I was, I liked to play the… I liked some of the Bach pieces and some of the minor key stuff, but if… I was thinking if my piano teacher were alive today, she would just be in shock at where I am, like I was professional musician. But, and I think maybe for many reasons, maybe I was rebellious, maybe I just was very willful. I wanted to play electric guitar and I wanted to play rock music. So I got… I begged my mother for a guitar from … You know, it was called JCPenney Catalog.

And I got this Harmony Strat, it was a little set, a kit, and then very quickly I started my own band, my kind of basement bands. And then I was playing in bars when I was 15, like I guess what you call Classic Rock now and Southern Rock and Heavy Metal. I loved, I was a shredder. And sometime around that time there was a little independent radio station that had played bebop and I heard Sonny Rollins and I heard Charlie Parker and I was… I didn’t know what I was hearing. It blew me away and I was curious about it. And also I wasn’t doing well in school ’cause I was playing in clubs and stuff. So my mother said you gotta get it together. And I said, well, I’m just gonna be a musician. She said, well then you have to study. You can go to music school.

I was like, oh, okay. All right. So it was sort of perfect timing ’cause I started to hear this music and she connected me with, in Pittsburgh area is where I’m from, there’s a whole kind of… Actually an amazing jazz guitar tradition in Pittsburgh … Pennsylvania for anybody not in the US. But I met a teacher, John Maione, who taught at University of Pitt, and that’s how I saw Tal Farlow, who was like the real first jazz guitarist I ever saw. So I was probably about 15 years old. He came out of retirement and it was mind blowing. And that was sort of it. But I was still, you know, I was just still on the shredding. If you hear any of the stuff I do with Anat Cohen or any people like that, I still use that facility and sounds. I just love great guitar playing.It’s not genre based.

But I do love to swing. I love swing and I love that language. So, yeah. Then I spent a year in Pittsburgh at Duquesne University, which had a great, still has, a very great jazz guitar program. Joe Negri is the sort of the … well, Jimmy Ponder, of course George Benson and Joe Negri, who was on children’s TV in this United States and was a local TV personality in Pittsburgh.

So through all those people, there were a lot of great … I used to see Ella come through Pittsburgh when I was a kid and Joe Pass. And I heard Herb Ellis and I heard Count Basie. I mean, there was at the time all those folks who were coming through Pittsburgh and I was just eating it up. So then I went to Berklee after a year at Pittsburgh, I went to Berklee. And so that’s kind of the basic beginnings of …

Greg: So you were kind of like swimming in the ocean of amazing music it sounds like through those years.

Sheryl: Also my mother was incredible, (she) was a great pianist and so I was … When I was a kid we had pianos and everyone played and I’d go to my friend’s house and they didn’t have a piano and I couldn’t wrap my head around it. It was like, what do they do for fun? You know, we were like a musical theater family and we played together. And maybe at the time, when I was a teenager, I thought it was kind of corny. But now when I look back, it was really beautiful thing that we did together as a family to sing all the songs from South Pacific or the Sound of Music or something as a family. It was a beautiful thing.

Greg: That’s really interesting you say that. I had the great pleasure of studying composition for a while with Glen Jordan. He did a number of film scores. But he was connected with Spud Murphy, the great arranger of the Benny Goodman lineup. And Spud said something very interesting to Glen once, which was, you know … Maybe it was Glen that was saying … He thought the reason there was so many great musicians back in those days was because they really didn’t have much television or sort of other media to kind of just sit there and distract people all day. They had to find ways to entertain themselves, beyond just kind of getting spoonfed things off the television, you know?

Sheryl: Yeah. You know what blew my mind actually, when I went to college and I had to be in the madrigal choir, and that music was so difficult. And they were like, this was the people’s music.They would get together and sing that stuff. I was like, okay, we must be heading towards stupidity ’cause this is incredibly complex music. (laughs)

Greg: Yeah. Very interesting Sheryl. So … obviously now you’re one of the most highly acclaimed jazz guitarist of the present day … What do you think has made … Well this is what Vin’s put on these questions, right? But I believe it as well.

What do you think has made you really exceptional, you know, like at the top of the game in terms of jazz guitar? What do you think has been those key ingredients or connections or influences that has made you into what you are today?

Sheryl: Well, that … you know, I love practicing. I practice a lot. I’ve studied a lot. When I was, particularly as a Berklee student … I transcribed stacks of stuff. So there’s that thing, the discipline of study, but also playing with others and playing with people that are better than you.

You know, it’s sort of like if you wanna get good at a game, you have to play. ‘Hey, I wanna be a great basketball player.’ If all you do is just sit and dribble with yourself, that’s a part of it, but that’s not really the game and developing how to play the game. So I think that’s the other thing.

It’s balancing those things between study and learning about the technical aspects of whatever instrument you play. But then playing it with others. So actually what your friend was saying about it being a contact sport is so important in terms of growth and how you develop and how you learn.You have to play with others and for others also. You know what I mean?

Like those kind of moments when you’re playing, I’m thinking about actually … I had played guitar night last night with Frank Vignola and Pasquale Grasso at Birdland. So you know, Wednesday nights New York City go to Birdland. But that experience of that intimate way that we were all playing, with the audience involved is so powerful.

So it’s all those aspects. Playing together with others and playing together with others, for others, will make you grow and become a great player over time. So, I mean, easier said than done. Obviously we have to deal with our own fear and own inner voices that keep us from… first of all, even just the first part … of having the discipline to sit down and study and work on our thing.

And then all the voices, and doubt and stuff. They make it scary to play with others, like to play with people that are better than you. Right? So, you know … We could talk about that too, you know … All that’s fascinating. Just the whole process of developing musicianship.

Greg: I think that’s something that holds a lot of jazz, aspiring jazz guitarists back, or jazz players in general, is that sort of fear they’re not good enough, you know?

Or in terms of crossing the barrier. And sometimes it kind of is reinforced if you go to a jazz session and there’s people that are kind of flexing on you a bit sort of thing. You know, trying to kind of vibe you out, you know? Have you ever, yourself or your students, experienced those situations? What would you say would be the best way to navigate that kind of circumstance?

Sheryl: Hmm. Yeah. I mean, that is difficult. I mean, things are changing I think, a lot. I think people are consciously trying to create spaces to play together that are vibe free. But you know, it’s gonna happen.

You know, I don’t know. I always say, what doesn’t kill you makes you stronger. That’s kind of the philosophy of living.

Vin: Sink or swim, right?

Sheryl: Yeah. And there is something about that because you do need a lot of strength and, I don’t wanna say ego, I don’t mean that in an obnoxious way. But you have to be, you have to develop that ability.

Well, my colleague David Tronzo, professor David Tronzo always says “who’s my favorite guitarist? Me.” If you don’t have that forefront, then why is it, why are you gonna take care of yourself and take care of all those things and put yourself in those situations? But I guess not to be … I’m not talking like big ego, like arrogance kind of thing, but like a strength that you have to develop in yourself.

Greg: Exactly. It was interesting. I’ve read or seen an interview with Pat Metheny when he was saying something like, what’s the main thing he thinks about after he does an amazing concert and he says, “well, you know, I sit there and go ‘Man, I really need to do some more practice.'” So I think it’s sort of feeling of needing things to be better affects all musicians at all levels. To a degree I don’t think it goes away. But as you say, you really need that self-confidence to be able to get yourself out there, you know?

Sheryl: Yeah, I think it’s a balance. I mean, you need that honest … I’ve given up being objective on my playing and in some ways it’s made me … objective. Like, I don’t take it personally and I sometimes just listen to myself. If I’m analyzing a recording and just listen to it as if I’m listening to someone else. Not personally. And I think that’s important to be able to separate yourself so you can go hey, I have these weaknesses.

I mean, everybody has weaknesses. Even Pat Metheny. He knows what he perceives as his weaknesses or else he wouldn’t keep practicing, right? He’d just hang it on the wall and say, “hey, I’m it. I did it.”


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Greg: So let’s kind of think … I’m going a bit off script here Vin, but while we’re on this topic… I’m thinking when you’re… Let’s say you have a student, Sheryl, and you’re trying to get them to get out there a bit more and play. What advice would you give to them to prepare, say for, not maybe a big concert or anything like that, but just going down to a local jam session or something, how would one prepare themselves for that?

Sheryl: That’s a great question. You know, first thing I always say is just go to the jam session a couple times and observe it. See what tunes they play. ’cause you always find certain groups of people call certain tunes and in certain cities call (tunes). So you know, there’s just like a repertoire. So find out what tunes that they commonly play.

Find out who … Just observe who’s the leader and kind of check out the vibe. Does it seem friendly or is it vib-ey? Because if you wanna go and it is vibe, just set yourself up for that. Like, don’t take it personally. There’s nothing personal about you, that’s just the way these people are carrying on.

But I think the main thing is find out what tunes to know, to come and be prepared. So that when you get your chance to sit in you’re not freaking out. ’cause ‘oh my God, they called this head and I don’t know it.’ So I think that’s one. And maybe just get to know the people a little bit and they get to see you.

So you start that relationship. So I think when you get to that chance to finally get on a bandstand, you’ll feel a little bit more at home there.

Greg: Yeah. It’s sort of classic networking techniques, isn’t it, really? Like, firstly you need to get visible and then once you’re visible for a while in a group, then you get credible and then you start to be able to kind of really make some great music and sit in and all that sort of thing.

But you can’t just sort of go in cold, ’cause you’re going into people’s space. You gotta kind of, you gotta warm up a bit, isn’t it?

Sheryl: Yeah. And just see how they… sometimes some jam sessions they make you sign a list and they’ll just go down the list.

Sometimes they just call people up just see the vibe and the feeling of it. But definitely find out. Oh yeah, they like to play All The Things You Are, they like to play Stablemates or they like to play Donna Lee. Or find out what ballads they like to play and then you’ll feel, okay I’m gonna learn those so I can have something to play when I show up.

Greg: Fantastic. Great advice. So Vin, do you have any other questions on that, on that topic?

Vin: Not on that particular topic. I’ve got a couple I’m kind of waiting to throw in.

Greg: Yeah, go for it. Go for it.

Vin: Well, I know Sheryl in 2010 you had the tribute… Emily Remer tribute cd.

Sheryl: Oh yes.

Vin: Can you tell us how that came about?

Sheryl: Ah, well that’s interesting. You know, actually, I was playing at the 55 Bar with my band and Marty Ashby, who’s the producer at MCG Jazz, which is a Pittsburgh label, believe it or not. But Marty’s a fantastic Grammy award-winning producer and guitarist.

And he was in New York and he popped in and he heard us play. And then he came up to me after the set. And I knew who he was. It was the first time we met and he said ‘oh yeah, I wanna do something with you.’ And I was like, sure, great. Let’s do it. And fast forward … Maybe he took another year.

I didn’t hear from him. And then he brought me out to Pittsburgh to play a festival. And then we sat down and met about what to do. And he was very close with Emily. He and his brother, Jay Ashby, who plays that incredible trombone solo on Emily’s tune ‘East to West’. And if anyone gets the cd, there’s a picture of me next to this big oil painting of Emily, and that was on Marty’s wall right behind him.

And we were sitting like, what should we do for this record? I looked up and said  why don’t we do something for Emily? And he just lit up. And that was like ‘oh, that’s what we’re gonna do!’ So that’s … But I guess that’s sort of also the story about you never know who’s listening at a gig.

Vin: Well on that, I was reading an article, I believe it was Jazz Times, and it was about this tribute CD and yourself. And it mentioned that you had actually met Emily and had taken a lesson from her.

Sheryl: Mm-hmm.

Vin: I’d like to hear about that!

Sheryl: Yeah. Well I actually even have the paper that she wrote on, which I share with my students all the time. She was in Pittsburgh. Well, that’s how Marty got to know her and … She was very instrumental in Marty getting the gig at MCG Jazz. So it’s just this funny, weird little connection.

It was my first year at Berklee and David Budway, who’s an amazing, amazing pianist. And he’s a Pittsburgh guy, calls me, it’s spring break, and he said “Hey, Emily’s in town. Here’s her number. Call her up for a lesson.” And I did. And you know, it was … It was cool. She was a great teacher. I mean, she was a great player.

She was a great composer. She was a great teacher. And I have all the sheets and I use everything she taught me every freaking day. I mean really, everything. And I use everything she taught me with all my students. And we just hung out. And she was super cool. Like, she wasn’t looking at her clock like, ‘oh kid, come on.’

Sheryl: She was like, ‘Hey, let’s play, let’s play.’ And we hung out and played all afternoon. She was so giving and just … it was a really positive experience.

Vin: Very cool.

Sheryl: She came to play at Berklee just right after that. So if you can find it on YouTube, which blew my mind because there was me and my friend Evelyn, (who) were the only two women studying guitar at Berklee.

Emily came and it was a concert, and she played her freaking butt off with ‘SCO’, Mick Goodrick, John Abercrombie. You can find it on YouTube. It’s a little grainy. But I was at that concert and she was on fire and then, you know, she was off drugs. She was … And then she passed a couple months after that.

Greg: Wow. Yeah it’s very tragic what happened there. You know, a career cut short, a life cut short, but … yes. You know sort of carrying that flame forward, Sheryl.

I’d be interested to delve a little bit into what it’s like being a female jazz guitarist in this space. You know, which is predominantly featuring men.

So how have you found to negotiate that? Has it been an issue or not really? Like, what’s been your experience as a woman in jazz guitar?

Sheryl: Well first of all, gender’s all big topic these days, right? I’ve kind of always believed … I don’t really attach myself to gender. I actually kind of dig these people that call themselves, ‘they’. I mean, I’m kind of like … I’m not … being a woman, what the hell does that mean? What does it mean? It means something more maybe to other people than to me. I have to pick up the guitar and play at my best. And I’ve always said there’s only one list. There’s not ‘the best woman guitar.’ There’s one list. Either you can play or you can’t. And that’s all I’ve ever cared about.

So I have rarely spoken about it because of that, because to me personally, my experience doesn’t mean anything. It means more to other people (who may) have issues with it. And yes, I’m sure … And I know there are many people that did not call me because they didn’t understand. But I can’t worry about that, can I? I have to play my guitar right now and make it sound great.

So that’s my experience with it. Flash forward, having told you that I was one of two women at Berklee, to be the assistant chair of the guitar department at Berklee with my chair, who is also a woman. That irony is not lost on me every day, and I do appreciate it more in terms of that representation.

Now we have probably … Maybe we’re up to 10% female… you know, young women in our program. So I do appreciate that representation makes people feel, in terms of other young women coming into play, makes them feel welcome in a welcome space.

To me personally, playing the guitar, it’s the same. I have the same struggles and problems that you guys have. Where’s A flat? Oh, this tempo. What’s the melody to this song? Just to me, human. I’m more of a humanist. I see the world as just humanity than these categories, but that’s just me.

Greg: Well said. Well said. Completely agree. So … Thank you for sharing that, Sheryl.

So let’s talk a little bit about your experience as a teacher now. You know, as you mentioned, you’re the assistant chair at Berklee. What do you think are the most important things for jazz guitar students in terms of what they do day to day in their practice session?

Let’s say you had, and let’s really take it back … I know you probably wouldn’t work with many students like this all the way at the start of their jazz journey …

Sheryl: No, I love that, I love that.

Greg: Oh, you love that. Oh, there you go.

Sheryl: I love it. I love the … Actually those are some of my favorite students, to be honest.

Greg: Oh, there you go. Well, this is a particularly good question for you then.

So let’s take one of those students starting from scratch. What would be their logical progression of exercises or, you know, the core fretboard knowledge, things like that. When it comes to learning jazz guitar specifically, what journey would you take them on?

Sheryl: Yeah, well there are many things about playing the guitar that are not genre specific. Musicianship, right? So whether you play heavy metal or bluegrass or jazz to understand your fretboard, right? Melody, harmony and rhythm right? Now specific to jazz, I think the most important thing is to listen to jazz and love it if you wanna study it. Now I think many people study it because they think it’s hard or something, or they think … you know, which is fine. I think everybody should study because I think understanding harmony in particular, we are a harmonic instrument, the guitar, after all. You know, whether they become jazz players or not, will of course enrich their musicianship.

So I just think of musicianship as universal. So yes, learning to read on the instrument. I know no one wants to do it, but you will …it actually is the fastest way to learn your instrument. To know all the notes on it. It’s also important in terms of being able to understand music, right? If you can read music, that means you could get a Charlie Parker Omni book and analyze it and understand, and you could play it.

So it opens the door to the world of music and it helps you notate it so that if you have ideas, you can share them with others. So I think that’s a number one thing. And so many people are freaked out by and scared of it. But you know what? Find a good teacher who just helps you work on your reading.

And to be honest, all you need to commit to is 10 minutes daily to get started. And you know, just try it. Because if somebody said the year’s gonna pass either way. So if you don’t work on it at all this year, next year you still won’t be able to read. But if maybe you start working on it, by next year you’ll actually be able to read something.

So I think that’s important. But you know, I came out of the William Levitt books. The Berklee books. In fact, I’m not pushing this book, but it is … we just put out a book called Guitar Theory, which is the history of the Berklee Guitar program. But also what we teach in our final exam. But that comes out of, the core of that, is really William Levitt.

So ‘A Modern Method for Guitar’. Dry as a bone. There’s nothing sexy or exciting about it, but if you really wanna learn your fretboard and all your major scale fingerings… Everybody’s gone through it can testify … Vin?

Vin: Yes. It’s … thorough. It’s thorough. Nothing if not thorough (laughs).

Sheryl: That’s what I’m saying. It doesn’t have to take up your life, but make it a little part of your life and it’ll help you. So we have scales to learn to learn the fret board, and that’s … We have harmony, so chord voicings, how to voice chords, how to voice lead. And also if you’re talking about jazz guitar, rhythm guitar. Number one. Learn to lay it down.

That’s probably the number one, with what we call shell voicings … the root, third, seventh. Listen to Joe Pass, listen to you know, any great … anybody great. Bucky Pizzarelli, all of them. To work on steps, to swinging that quarter note and rhythm guitar. That’s what I start with everybody. That’s the foundation, that’s the heartbeat.

That quarter note, learning where that quarter note is. But then it gives you a way you can play through tunes. You can, you know … One of the things I start with students is this thing of working on good solid rhythm guitar so that you can make your own rhythm tracks. So then you say ‘hey, I wanna learn this song called  Ornithology’ or blues, it doesn’t matter.

You can make your own rhythm guitar tracks and … But in doing that you learn the harmony and you become a great rhythm guitarist. If you become a great rhythm guitarist, you’ll be able to get into the contact sport that we were talking about. You’d be able to play with others right away.

But also when you’re playing rhythm guitar, if I’m playing rhythm guitar on a blues … B flat… E flat … Okay. When I’m soloing, guess what I’m thinking? B flat … E flat … B flat… They’re the same thought process. It’s all connected.

So I can tell even some of these students at Berklee that play, by all means they’re advanced players, but I can tell within a measure whether they’re gonna be a good rhythm guitarist by the way they play the melody. It’s connected, that foundation of the quarter notes. And then most of the time I know it’s gonna be a drag when I go to solo. ’cause the quarter note’s not gonna be there for me.

So that to me is one of the most fundamental things to get together, is that you’re developing your feel and your sense of time. And then harmonic rhythm. And then you can start to play tunes. You can start to learn tunes and play with others.

Greg: That’s the thing, isn’t it? Because when you’re at a jam session, probably 90% of your time is playing the rhythm anyway as a guitarist. You know, so the bar might be a bit lower.

Well obviously, no, it takes a lot of work to become a great rhythm guitarist, but in terms of being able to attend a jam session, maybe don’t focus so much on the whole soloing thing. Just keep that to the basics, but really make sure your rhythm guitar is rock solid. Yeah?

Sheryl: Yeah. And it’s gonna make you a better soloist. Because A, you’re gonna know … I mean, jazz in particular is a music of syncopated rhythms, which means rhythms that are on the upbeat. But if I don’t know where the downbeat is, how do I know where the upbeat is?

That’s what I’m talking about. Like really locking that down. And I could tell that in even some of these ‘advanced students’, they haven’t worked on their quarter note. And their syncopated rhythms are all over the place. They’re not in the pocket and grooving. So it’s always, to me, it’s always going back to that fundamental. Myself, I love to play … I could be happy playing rhythm guitar just as much as I could be happy soloing. They’re not separate to me. They’re fun. They’re both fun.

Greg: Very interesting. That’s great advice to … make sure you write notes guys who … If you’re listening to this podcast right now, ’cause that was a real gem of wisdom right there!

So let’s keep talking a little bit about some advice you’d give to budding students. Let’s now talk specifically about, improvisation, right. So … because that seems to be one of the big nuts to crack when it comes to jazz, is to feel confident, improvising, feel prepared, and to be able to kind of make something meaningful spontaneously. So what advice would you give? Let’s say you had a student today.

What advice would you give them in that regard when you’re focusing mainly on improvising?

Sheryl: Well, that’s hard to say in a generic way. I mean, obviously we’re talking about a language, a very complex language, right? So the deeper … And I always use this parallel, if you wanted to learn French, there’s a couple levels. Like, hey I’m going to France next week. I need to learn some basics. ‘Hello? How are you? Where’s the bathroom? What’s for breakfast?’ Whatever. And I’m probably gonna spit ’em out and people will look at me like, okay that’s survival skill of the language. But hey, maybe I wanna get deeper inside of there. And so what am I gonna do?

I’m gonna listen, I’m gonna, you know … well first I’d probably get a teacher. I’d start to learn more vocabulary, grammar. I’d watch French movies. I’d eat French food. I’d get a French poodle. I’d do anything to just immerse myself in the culture and the language. And then … So then you have that level.

Okay, now I’ll go to France and I can get around and I’d get directions and people understand me, but I can’t get into a deep conversation. So it’s always this deeper and deeper layer of learning a language. So when do I know the language, I’ve mastered it? I’m dreaming in it. I can tell jokes in it. Or I can get jokes in it. That language, right? Or I can write, I can … So that’s fluency, right? So there’s all those levels about how deep into a language do you wanna get. So my language now is bebop and contemporary jazz, that I dream in, that I can speak it fluently. But I’ve started in those little steps. And again, I think there’s something for everybody at every level and every stage.

You don’t have to go in all the way. Maybe you just stick your toe in there and you learn a couple, what we might call ’em, some licks, some little phrases. That’s cool. It’s all good, I say. Let everybody come in there and experience it.

Greg: Yeah. Awesome. So I think that’s a really interesting slant there, Sheryl, because what you’re sort of saying there is, obviously we are talking improvisation, but the term might be a bit misleading. It’s more like, the speaking language musically, you know? And that’s a different slant on it, isn’t it? Rather than, I’ve gotta think … Come up with stuff that’s never been done before. It’s more you’re expressing your ideas through the language and that takes training, study. And as you say, maybe if you’re starting out, a few stock phrases just so you can get by.

Sheryl: Yes. I think so. And developing your voice through it also. I mean, that’s a whole sort of process, but you know, everybody plays … If you go to hear John Scofield every night of the week, you’re going to hear his tendencies. Everybody has their tendencies, but you know in a way, what’s cool about jazz is we have that liberty to develop our own unique voice. But he’s not coming out of nowhere also. Know what I mean?

He transcribed tons of horn players and piano. His voice is part of the tradition now, and it comes from the tradition. So I think that’s the thing … there’s some point, I think every player really gets into one player and imitates them and really uptakes it in that way.

And then there’s some points, sort of like training wheels where they… Bill Frizzell … I think it was a legend that he learned everything Jim Hall. Even played the same guitar. And there was one point he just … He took his book and burned it basically. And Bill Frizzell does not sound like Jim Hall, but Jim Hall’s influences all over him.

He became his own voice, you know? So I think that’s also the beautiful thing about falling in the tradition. At some point you have that liberty to create your own sound.

Greg: Moving on. So, maybe just a couple more questions if you have some time. So, I guess we might be going over things you’ve already covered, but even at a pro level, what are the … or regardless of level, maybe we’ll just think about what you’ve seen over your career, especially teaching. What are the biggest mistakes and myths when it comes to learning jazz guitar or guitar in general. Where do you find people, even at a pro level, wasting their time a lot on things that don’t really matter, for example. Have you sort of come across anything like that?

Sheryl: Wow, that… Whew. I don’t know. You know what? Maybe comparing yourself to others. You know what I mean? Like that could just eat you up. You have so many great players out there when you go out, I think that could really throw you. That could throw yourself under the bus. I guess that’s the one I could think of.

Greg: Wow. Yeah. We’re our own worst enemy sometimes, isn’t it?

Sheryl: Absolutely. Well, I felt my journey moving to New York was that. Like, you’re so excited. There’s so much music here and so many musicians. And you go out every night and you hear Mike Stern, then you hear Steve Cardenas and you hear Peter Bernstein.

Then you’re like, oh my God. And then you pick up your instrument and you’re like ‘but I can’t play like any of them.’ And that again, it’s sort of the thing. What doesn’t kill you makes you stronger. And then you have to search under those. Well, what do I do? Who am I? So I guess that’s maybe what I’m thinking about.

You go out there and you’re like, see all these great players. There’s so many players. So finding hopefully that instead of it eating you up, it’ll bring you to that place of fine, well, who am I? What do I do? For me, the way I found myself was through writing and playing with my own band. Because you know, you wanna play. I would try to play repertoire, Wes Montgomery, and then you’d be like oh god, I don’t sound like Wes. You never will. There was only one, you know? And Wes wasn’t trying to sound like anybody else. He was just doing his thing. So I guess finding that place where you … But for me it was through writing and just kind of building my voice around that.

Greg: Amazing, fantastic advice. All right. I guess following on from that, … as a teacher now, we’re instructing a lot of enthusiastic players all around the world. So for us teachers, how do you think we can help our students become the best musicians and jazz players that they can be? What advice would you give to teachers?

Sheryl: Yeah. You know, the more that I’m around the planet and teaching, learning how to practice is the most important skill. Because again, that’s universal. So I’m talking about fundamentals, posture, relaxation, breathing technique, like the physicality of playing the instrument and developing that.

And also how do you use your time when you practice. If you can get that worked out you’ll be able to make progress. But I think there’s so much stuff out there. So many students are overwhelmed by too much stuff. So I think it’s being able to sit with a student and help them craft their pathway of what goals are important to what they are doing right now. Because of course, you know it’s gonna change.

What you practice, Greg, and what Vin, what you practice and what I practice are all different. ’cause we have different weaknesses, we have different goals, we have different things going on. So our students do too. So I think it’s a matter of being able to connect with them. Zero in on that and helping them.

It’s kind of like teach a man how to fish. But if you could teach them these things… But definitely the fundamentals of the physicality of practice and then the practicality of planning practice time for the best results.

Greg: Yeah. I’ve got a mentor of mine that often talks about signal versus noise. You know, there’s so much noise out there, but where’s the signal? Where’s the essential bits? Because especially nowadays, there’s a plethora of all sorts of courses and videos and blog posts. You can go anywhere you like and find a different opinion, a different approach, and they’re probably all great. But what’s the real key parts?

So I think having a really clear guide, someone like yourself, Sheryl, that can really guide students through the noise and find the signal. Really important I think.

Sheryl: Well I would say that … yeah, there’s a thing like a collector mentality and people are collecting, but they can’t actually sit down and play through a whole tune.

So with all of ’em, I’m like, it’s not what you’re doing, it’s how you’re doing it. They kind of have … They don’t have their left hand or whatever. It’s not speaking, the notes aren’t speaking. They’re posture, they’re not breathing. I’m like, hey let’s work on playing this really well.

And building a foundation, like in terms of even that stuff. Going back to your rhythm guitar and just accomplishing that and build from that. And don’t worry about collecting all the things, you know, just work on… Or even if it’s like working on your technique, like playing a scale with nice legato and connected in your times. Good. That’s an accomplishment. You’ve accomplished something.

Greg: There’s an old proverb from India I think. Imagine you had a concrete block, right? And then you get a big bucket of water and you just pour the whole bucket of water on top of the block and the water just splashes off everywhere.

But let’s say you just have a little drip just kind of going one at a time onto the block. Over time eventually it’ll actually make a hole through the rock, but splashing a whole bunch of water on top won’t do much, you know?

Sheryl: That’s great. Oh, I love that. I’m stealing that. Yeah,

Greg: yeah, no worries. So Sheryl, before we wrap up is there anything you’d like to share with our audience in terms of recordings or any programs or anything like that that you’d like to talk about?

Sheryl: Sure. Well I’ll tell you one thing. This (holds up vinyl album) just came out. It’s actual vinyl and it’s my band, my quartet with Harvey S,Neil Smith and Mickey Hayama. So it’s available on vinyl and digital download via me. So, I’m kind of trying to take back the ownership of my art, right? So you can get it on my webpage. But you can get it for free on YouTube.

And so check it out because it’s a series of each cut. And then it kind of … The next video is a story about it, kind of a lesson or maybe story about how did we record this, how did we think of it. So that’s on my YouTube. So you can hear the whole thing and learn about the thing, on my YouTube page, which is just Sheryl Bailey. I do have many courses available through TrueFire and my own artist channel there.

It’s a subscriber based thing and you can study with me, private lessons. It’s kind of the only way that I’m teaching these days. So, Truefire. I’ve worked with them many years. I have only glowing things to say about them as a business and an educational platform. And also I have stuff with Mike’s Master classes and Jazz Guitar Society. There’s a ‘Giant Steps’ course that I think is pretty cool. And if you’re in Boston, stop by 921 Boylston Street, fourth floor. Say hi to us at the guitar department. Or anywhere that I might be playing. So those are the main things that are going. Also, I have a record … I started working with the great Jerry Bergonzi, tenor player in Boston.

So that was sort of a cool thing about starting to be in Boston. So I have a record with him. His record is coming out in October, which was really a joy to record with him. We kind of have a new project coming out. I don’t know when it’s gonna come out. It’s called Taurus Power, that features Jerry.

But anyway, Jerry’s record will be out in October.

Greg: Let’s listen to a recording off one of Sheryl’s albums now. This one’s called ‘Walkup’ and it’s from the album Homage, from Sheryl Bailey with her band, SBQ. So let’s roll the track and I’m really excited to listen.

(Audio track plays)

Greg: So that was ‘Walkup’ by Cheryl Bailey and the band SBQ.

What a fantastic chance that we’ve had today to talk with one of the great luminaries of jazz guitar and jazz guitar education. Sheryl Bailey, it’s been fantastic having you join us today on today’s show. So Sheryl, any final advice or … How would you like to close off today’s session?

Sheryl: Yes… if you’re a student of the music, which we all are, and I still am … Those that ask the most questions, get the most answers.

Greg: Fantastic. All right. I’m gonna definitely be sitting on a mountaintop today, meditating on that one for sure. So anyway, thank you very much Sheryl, and thank you for joining me today Vin. This is Greg from the Fret Dojo podcast and we’ll look forward to seeing you in another episode soon.

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1 Comment

  1. Joseph

    Hi Greg,

    That podcast with Sheryl Bailey was absolutely fantastic.
    So many pearls of wisdom. It will take time to process it all.
    Thank you and many thanks to Sheryl.



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