David Watkins To Play Jazz Legends in One Man Show ‘Satchmo at the Waldorf’


There are American legends and then there are American Gods. Louis Armstrong and Miles Davis appear in the latter category. Their personas could not be more different, their styles, their paths, their acceptance in their time, and the secrets that have bled out into the light after they’ve gone. This upcoming month, all month, the VA Repertory Theatre is showcasing a one-man play, Satchmo at The Waldorf, that humanizes these legends through the talents of two outstanding actors. They both take several of the performances each week. David Watkins is one of them. We were lucky enough to catch him at the theater before one of his rehearsals to shake him down with some questions:

actor David Watkins, Satchmo at The Waldorf at VA Rep_interview by Chrisitan Detres, RVA Magazine 2024
Louis Armstrong 1955

David Watkins: Give me your worst.

Christian Detres: Challenging me already? All right. Let’s go there. Tell us a little bit about who you are, how you’re coming here to this theater, and specifically, to this show.

DW: I’m from Long Island, New York, moved to Richmond, Virginia, moved to North Carolina to go to North Carolina A&T State University, home of the Aggies. Shout out to the late Ms. Day, my awesome school director for theater. Moved back to New York. Lived in New York for a long time. Got to Philly, now I’m back in Richmond. I’ve been singing and dancing and performing on stage since I was seven years old. I did the whole Michael Jackson “Smooth Criminal” routine at my elementary school talent show for my first performance. My mom bought me the white suit, the white hat, the whole thing. I got a standing ovation. I was seven. What did I know? I just never wanted to get off the stage. I knew that.

Off of the stage, I guess you would call me an introvert. A pivotal moment was in high school. I had a choice between basketball and theater. I just took the whole Summer getting really good at playing basketball. My brother’s an amazing basketball player. I wanted to be like him. Tryouts were the same day as auditions for the theater show. I think Guys and Dolls or something like that.

CD: I’ve done that show too! I was Big Julie!

DW: I already had a spot on the team and worked all summer with the coach. He was like, just come on in. You ain’t gotta do nothing. I chose theater. He was so angry. I never looked back.

That same year, I got a scholarship to Liberty to play basketball out of the blue. I just kept going and went to school, and hit the road, did the whole New York thing. I beat in the street, got holes in my shoes just trying to find something. It has all led me to the Virginia Rep. Doing Satchmo. It made sense to be here. Having family close just kind of puts a cherry on top. 

CD: Tell me about this show. In Satchmo, you’re playing three characters. I’ve done the “get real deep into one character” in my stage days. Applying Stanislavski method acting, you know, really getting in the head of this character and living it. It’s a near self-induced trance that requires a lot of mental discipline. How do you do that with three very intricate personalities to portray?

DW: Well, first off, I am Stanislavski trained, so I totally understand why you’d ask that. At first, it is challenging because it’s a quick switch between characters. There are some very intense moments in the show, and it’s just me up there. I’ll have one intense moment with Louis and then it switches into a happy moment with a different character. 

CD: Yeah, we’re talking about mad different people in Miles Davis and Louis Armstrong. Yeah, I mean, I’m not so familiar with Louis Armstrong’s manager, Joe Glaser, but I can’t imagine he isn’t also a very conflicted jazz legend. There’s a different well to go to for him, I assume. 

DW: He’s his manager / mobster ‘promoter’. Just one of those slick guys trying to make a buck. Switching is difficult until you really get into the story. So like, for my process, it was Louis first – like let me get all of what he’s trying to say in this piece. I’ve watched a lot of concerts and interviews and shows and just listened to him. I’m still listening to all of his discography. I’m never going to be Louis Armstrong, but I can get the spirit of him, I can channel what it is that he’s saying. And then Joe Glaser’s next. I get into his spirit, soak in it. It becomes easier to kind of ‘double-dutch’ it. After that, well, I’ve always been a fan of Miles Davis. So getting into him and just his coolness… I mean, it’s Miles.

Miles Davis 1951
Miles Davis 1951

CD: I don’t want to say he was an angry man, but he always seemed to me like he was stoned or about to stab someone. You say the wrong thing man…

DW: Yeah. He’s dangerous. Which makes his character come to life that much more. Their backgrounds, seeing how different they are, is fascinating. Everyone still comes together. So it’s very difficult and sensitive to switch. But once you get into the mindset of each of the three and really figure out what they’re trying to say, and why they’re saying it, then it’s easy to turn the lights on. Like okay, it’s hard to turn them off sometimes. [laughs]

CD: But that’s Stanislavski for you. Ruining actors’ mental health for nearly a century. 

DW: Right, but you know, as long as I’m not going on stage smacking people at the Oscars, I’ll be all right. 

CD: While researching each character, were there any particular insights that big fans of Miles Davis or Louis Armstrong – which is a group that comprises most people – would find surprising?

DW: I guess most people wouldn’t know that Miles’ upbringing and Louis’ upbringing were incredibly different. They, in their shared time, would still become these giants of music. Miles came from a well-to-do family. His father was a doctor and played at the country club, whereas Louis came from nothing. It’s something to see them both rise, Miles going to Julliard as a prodigy, becoming this amazing jazz artist, and then Louis, playing the same instrument, coming from the dirt. Louis started in the gutter and still had this drive to become this crazy artist. For someone like me that also plays music, it comforts to know you can withstand all of these things in your past, wildfires of tragedy, and you still can come out okay. 

You hear the same story everywhere, “rags to riches”. Everybody comes from the “hood” blah, blah. But then you see Miles. No, everybody doesn’t come from the ‘hood’. The flame that ignites still sparks. It builds your character and your instrument regardless of where you’re coming from. That’s why they’re so different and yet so amazing at the same time. 

To see Louis, to see where he was playing, and why he was playing the way he does in contrast to Miles? I know why Louis was at the predominantly white establishments playing to simple elegance. There’s an avenue for that. But then I see Miles as just JAZZ. It’s just amazing that you can come from anything and this musical spirit can be equally brilliant from any source. 

CD: I look at it like it’s an internal fire that doesn’t have an external beginning or spark. It gets convoluted or refined by external things, but it’s still a fire from inside – a curiosity that begets expression through interaction with the world. One of the dichotomies I wanted to look at was the difference between those two characters, but let’s talk about Glaser too. I don’t know much about him. I knew the story about the Chicago mob being something like a patron of Armstrong’s but I didn’t know… It’s hard to talk about all this without ruining the play, haha. No spoilers! Could you give my readers maybe a basic understanding of who this third “glue” character is? 

Louis Armstrong with Joe Glaser 1952
Louis Armstrong with Joe Glaser 1952

DW: Joe Glaser, or Mr. Glaser, as we call him in the show? Well, technically, he’s the manager of Louis Armstrong – the real manager, not the road manager. He comes from a Jewish upbringing. His father was a doctor. He wanted him to be a doctor, to live a traditional Jewish lifestyle. Joe was “for the streets” as the kids say nowadays (ed: not sure they do, but we get it). He got involved with Al Capone and lived a totally different life from what his upbringing would have predicted. 

He’s running clubs for Al Capone, managing prizefighters, cathouses etc. He’s doing all the dirty work. Then he discovers Louis Armstrong. He’s never heard anything like it, and immediately the dollar signs ring in his ears. He is why we know Louis Armstrong at all. He put in the work to make sure he got into the places he needed to be. Good work and some bad work. You’ll learn about that in the show. Everybody needs someone to believe in them enough to push them forward. 

CD: Who is that in your life? 

DW: Well, at first it was my mom. I don’t come from an artistic family. I’m the only one in plays and singing shows. I’m the youngest of three, so when I came along, my brother was in sports, my sister was cheerleading. I wanted to be in theater and be in the choir. I don’t think my parents understood that. Which is so strange, because my dad loves music. He has a million vinyls at home. I always tell him “these TV shows, and the music you listen to, are the products of people actually working. You’re enjoying people’s work. That’s all hard work.”

CD: In our popular culture, it’s a common understanding that artists “grind”. They grind hard to get that album out. They did this, that, and the other thing, and then hustled on the street giving out their CDs to people or whatever. And yet still, all that hard work gets labeled as “dream chasing” or my favorite “throwing your life away.” You’re better off working at a bank. 

An artist’s life involves a lot of hope. It involves a lot of confidence. It involves a lot of being okay with eating ramen between gigs. When the money’s not coming up. And it kind of breaks a lot of people sometimes. I mean, shit, I’ve been there. The bank guy, he doesn’t go for that. As long as he goes to work every day and clocks in at this time, gets out at that time, and doesn’t slack off and does the job, he gets a paycheck on Friday. He’ll get one next week, and the one after that unless, you know, something catastrophic happens with the company-

DW: I’m glad you said that. I love the grind lifestyle, because there is a form of danger with it. Yeah, but I have never seen the difference between that and what ‘they’ go through – especially these days. Downsizing throws these “bank guys” away like so much garbage when it suits the purposes of the Board, or the CEO. 

CD: So maybe the fragility that is portrayed in our business is not quite so different from the fragility of anybody working a “straight” job.

DW: I think so. I think with us, we’re always sold the dream at first. I think everybody, even corporate America sells it. If you do ‘this’, you can be ‘here’ in five years. Even with us with gigs – and especially with actors – “you can be Denzel!”, and it can happen, but the reality of just being humble and saying, “Okay, well, if you don’t do these steps, you know, and have a lot of grace and a lot luck… If you ain’t moving to LA; If you ain’t moving to Atlanta; there’s a certain humility that you have to understand. I wish that was more instilled. That’s what has been my greatest benefactor – knowing I know where I am, and eventually what I would love to be in. But, if you don’t get there, understand you can still enjoy the entertainer’s life without killing yourself. It’s not all or nothing. 

CD: We also have to face much more vocal criticisms. On top of the competence and persistence is a thick skin. Like maybe that’s something that bank guy doesn’t have to do. Damn, I can go off on a tangent. More about you and less existentialism. You’re a musician too, right? 

DW: I am a self-taught multi instrumentalist. My first instrument is guitar. When I first heard “Beat It” by Michael Jackson, I wanted to learn how to play the solo. I had never even seen anybody play guitar before until I heard that record. I was super young. The only other guitar player I knew played at my local church, but he didn’t play the way the guitarist on “Beat It” played.. He just played church music. So I went to the local music shop, bought the first guitar they had on the rack, got me a Guitar for Dummies book and learned how to play. Then my mom bought me a piano. I spent a lot of nights in my teens when I probably could have been out doing other things, learning instruments. So I play guitar, piano, organ, bass, and a little bit of drums. I have played the trumpet before, but for vanity reasons I stopped. I had two really nice ones and I was getting good, but it gives you that little lip divot you see on trumpet players. I couldn’t do that. [laughs]

Then I went to school. I got my first professional music gig. I went on tour as a guitarist for Rahsaan Patterson with his After Hours tour. I learned a lot. I was subbing in for Jubu, the (legendary) guitarist, so he taught me a whole lot. I don’t know why they were letting me sub in for Jubu. Like, he’s amazing. I was just starting. 

CD: They must have had some confidence in you. 

DW: I guess. Or I had somebody who knew somebody. And also, I was way cheaper than the other guy. [laughs] I mean, I got the gig. Done. Yeah. And then I self-produced four albums of my own. Recently, I became the new lead singer for the band Ready for the World. (ed: Remember the 80’s song “Oh, Sheila”? That’s them) We’ve been touring all over the country playing their hits. We’ve been working on a new project for them as well. I produce a lot of artists and write a lot of songs as well.

CD: I need a vacation just hearing you tell me about all that. That’s a lot. Do you play at all in the show?

DW: No, unfortunately not. We’re about a couple days out from the show opening. It’ll go very fast. 

Satchmo at The Waldorf at VA Rep
Satchmo at The Waldorf at VA Rep, buy your tickets HERE

CD: How long have you guys been in rehearsals? About three weeks? 

DW: About three weeks. It’s a monster of a script. It’s probably one of the most challenging. I did Seven Guitars one time and that was kind of on the same- it’s like 800 pages. But just the depth that you have to go to with this play is significant. It goes through happy moments all the way to hurt, and despair. I have to bring all of this out of me. And there’s nothing on stage but me.  

I say monster in a good way though. It’s a challenge. But I am grateful for it. And I think people watching it, they’re gonna get a lot of education, but also a lot of entertainment, from it. You’ll be learning a lot of things that you didn’t know, and feeling some unexpected feelings, coming out of this show. But, I’m just saying, shout out to Rick Hammerly. He’s done an amazing job. 

CD: I like that guy.

DW: He is capturing all of the funny, all of the sad, all of the hurt, all the anger, the betrayal- and he is making sure that it’s all represented. So it’s not going to be one way or the other. I’ve seen some shows where it’s just kind of one thing the whole time. You get the whole burrito in this one. It’s extremely mature. 

I’d only ever seen Louis Armstrong on TV. I didn’t know until I was doing research for this, that a lot of his personal self-recorded tapes still exist. You can go through the archive and actually hear him use profanity and get loose. I saw him as a regular guy. 

I had the opportunity to go to Paisley Park once. They let me go into Prince’s old office. They hadn’t moved anything since he passed and it was… normal. It was great just to see he was just a regular guy making music. So, when listening to Louis, and then listening to his dialogue, hearing him just, have fun, and tell jokes- It makes these genius people become just the same as I am. 

I think the beauty of this particular show is that we’re not capturing their music, we’re capturing them. So you can still come in with your appreciation of their iconic bodies of work, but understand, you’re gonna get something even more than just a concert. You’re gonna get to know Louis. We’ve gotten into the minds of Louis Armstrong and Miles Davis, seen how they really felt about things. You already know the music. You already know what you think you know of them. You know the smile, the voice. 

You know all of this about Louis but you don’t know him sitting down talking about his life, talking about the stories on the road, or talking about his wives. He says, in the play, that all of these experiences, this is what comes out of his horn. That’s why you love it so much, because when he plays, he’s playing about his mom. Or he’s playing about his upbringing, or when he had to dig through trash cans to find food and put bread on the table. 

I feel like this play gives you a new appreciation for their work. You’ll know why this favorite part of your favorite track is so intense. I can understand why Miles played like this, and Louis played like that. I can understand why he would play in a club where he wasn’t accepted. What if I can sit down with Miles and just have a real conversation? 

CD: What period or what moment in their lives is this show depicting? 

DW: It’s one evening after Louis’ five shows in 1971. He’s finished on stage with his record breaking “Hello, Dolly.” When our show starts, you see him coming into the dressing room after his show, and he sees you. He’s coming into change to go upstairs and go and take a shower and go to sleep, get ready for tomorrow. 

The audience gets to sit in his dressing room with him and have a conversation. And so he goes through all of himself. And it’s a great realization. When you get through maybe 75% of the play, something clicks. Oh, I don’t want to give it away, something clicks and you as the audience are going to see. You’re gonna go “oh, this is what this was all about.”

CD: Nice. Oh, I can’t wait man. How many shows are there? How many performances? 

DW: We open March 1 and April 7 is when it closes. 

CD: Okay. So that’s I’m assuming a number, you know, a decent number of performances. Yes. More than 10. [laughs]

DW: Yeah. So I’m doing the Wednesday ones. It’s Wednesday through Sunday, and I think there’s two on Saturday.

CD: Oh, nice. Okay, so people will have a lot of opportunities to say yes. I’m glad you’re enthusiastic about it. I think the theater seasons that I’ve been privy to this year in Richmond look amazing. There’s a lot of really cool shows. Across the board. I just went to Firehouse and saw Memories of Overdevelopment. Incredible. Amazing. Theater in town has gotten a lot more progressively intentional and intentionally progressive. This is certainly an example of that. Please break both legs my friend! See you on stage. 

Buy your tickets for Satchmo at The Waldorf HERE

Main photo: Actor David Watkins, Satchmo at The Waldorf at VA Rep, photo by R. Anthony Harris 2024

Satchmo at the Waldorf Trailer by Long Wharf Theatre 2012
Christian Detres

Christian Detres

Christian Detres has spent his career bouncing back and forth between Richmond VA and his hometown Brooklyn, NY. He came up making punk ‘zines in high school and soon parlayed that into writing music reviews for alt weeklies. He moved on to comedic commentary and fast lifestyle pieces for Chew on This and RVA magazines. He hit the gas when becoming VICE magazine’s travel Publisher and kept up his globetrotting at Nowhere magazine, Bushwick Notebook, BUST magazine and Gungho Guides. He’s been published in Teen Vogue, Harpers, and New York magazine to name drop casually - no biggie. He maintains a prime directive of making an audience laugh at high-concept hijinks while pondering our silly existence. He can be reached at christianaarondetres@gmail.com

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