At the close of 2019, I received an email from a former interviewee, Nathan Townsend, asking if I would do a profile on someone special, David Underwood.
He wrote, “It’s time for this talented Philadelphian to be acknowledged for the gift he brings to the world as the offspring of a talented musical family from North Philadelphia. One of Philly’s best-kept secrets and the world’s most beautiful voices packaged in a vessel that is coming to its own authenticity.”
I understand that you’re from a very musical family. Yes, my dad and my Aunt Veronica were musicians. I grew up in North Philly, in the Strawberry Mansion area. A lot of the family has performed, but mostly them.
Did your father mostly sing or play an instrument? My dad mostly plays the guitar, bass and piano, and he sings; my Aunt Veronica does vocals.
Did they perform together or on their own? Together. They had a band called The Underwoods.
What kind of music was it? Mostly R&B, some rock because my dad really liked rock. My Aunt Veronica was more into jazz; she’s the one who introduced me to it. She was a really big fan of Ella Fitzgerald, well, who isn’t, but that’s what I grew up listening to. We always had pianos in the house. People seemed to just donate them to us, so we always had about three pianos in a little row home on 33rd Street. I started playing around on them when I was younger, and I eventually taught myself to play.
So did you ever perform with The Underwoods? I did. My dad and Aunt Veronica stopped performing together when I was in my 20s, so my dad kind of had me step into her role. It was a little different for me; she’s a really strong singer in the gospel, R&B tradition. A lot of high soprano notes with runs and a lot of power, where my voice is quiet and sweeter; I’m more jazzy than gospel. I mostly sang with my dad and sometimes played piano.
Where did you study? I went to CAPA, the Philadelphia High School for Creative and Performing Arts. But I was a vocal major there; studying piano wasn’t an option back then. You weren’t allowed to do a double major. Later I went to Temple and took some piano classes but didn’t take private lessons until my 30s. I still try to take lessons every now and then just to better my chops.
When did you know that music was going to be it for you? I understand you initially did HIV testing and counseling. When I was about 19, I discovered the Attic Youth Center. I originally went there. I’m still working there now, just not in the same capacity. I quit when I was 31 and was working at another place doing the same thing, but it wasn’t working out. I started doing a lot more gigging; I started working at Tavern on Camac and other places in and around Philly. That was about 11 years ago, and I haven’t looked back. I’ve been able to sustain myself with music solely for 10 years now.
I recall singing a ditty or two with you at Tavern. Yes, I was there for 10 years, so it was bound to happen!
Where can we see you perform thesis days? Mostly in New Hope. I play at a place called The Cub Room every Friday night and at The Clarion on Saturdays. I also play a residency at the Paris Bistro in Chestnut Hill every first Saturday.
How would you classify your music? I love jazz, so I play mostly jazz — the American Songbook. Because I’ve been playing in piano bars for so long, I often mix in pop tunes with the standards. It keeps it interesting and helps pull in a younger audience. But I have to say, it’s also awesome to be back at the Attic. I run a music group there, which is also where I learn a lot of the current stuff!
Speaking of the standards, I think we both think the mellifluous Mel Tormé is underrated. Oh my gosh, yes. Mel is awesome and doesn’t get his due as a vocalist. Most people just know that he wrote “The Christmas Song.” He was a drummer too, which most people don’t know.
What do you do when someone requests a song? Can you just play things by ear? Sometimes, if I’ve heard the song before, but I do read music, mostly charts, but I can sight read as well.
Did you have any queer role models in the jazz world? Cole Porter, though he’s not technically considered jazz, Billy Strayhorn, Bessie Smith, though I’m still exploring her. She had a brassy sound that’s not quite my style, but seeing the movie [“Bessie”] sparked a lot of interest for me, and she spent a lot of time in Philly too.
When did you first come out? I came out as a lesbian in high school. I was 15, but I always knew there was something different, something else for me. I knew that trans people existed, but I was focused on not disappointing my mom, who kept saying, “You just want to be a man!” I kept saying no, because I didn’t want it to be true. So I didn’t come out as David until last year. I had to come out to my mom when I had a hysterectomy because of my fibroid tumors. My mom came to the hospital with me, and, at that point, all my doctors were used to calling me by male pronouns. So after the procedure, the doctor walked in and wrote David Underwood on the whiteboard, and I was like, “Aw man! So I guess I’m going to have to do this with my mom now?” And that’s how I came out to my mom just this past April.
Hopefully, the hospital drugs helped with it. [Laughing] Very true. I’d been thinking about it for some time, but in addition to worrying about my family, I was also concerned about what taking testosterone would do to my voice. So I just decided that I’d be a masculine lesbian — queer person — but then, I don’t know, I started to feel confined. After going through all of the medical issues I had last year, I said, I can’t not be myself any longer. I need to be who I really am.
How are you navigating the change, especially since people have known you in the public eye one way for so long? It’s hard. I mean there are so many people who still call me Dena. Just yesterday, I was walking home, and someone was calling me, and I didn’t even realize it because they were calling out, “Dena!” I kept walking without realizing he was talking to me. In some ways, it was kind of cool. I used to be surprised when people used David, and this showed how far I’ve come that I’m not responding to Dena anymore.
You’ve performed all over the place, what’s one of your favorites? I’d say the Kimmel Center. You know how they will have mini-concerts be in the atrium before the main show? I’ve done that a few times, and I really enjoyed it.
What’s the craziest thing that’s happened musically? I was asked to play for a funeral, and they had a piano there, but it wasn’t tuned, and some of the keys were dead. They then asked me to accompany one of the guests, I asked, “What is she singing?” “We don’t know.” It was crazy. I got through it, but … uh uh.
Do you get a lot of drunk folks? Absolutely, and they lose all sense of boundaries. I had one woman just come sit next to me at the piano, and after I finished the song, she planted a drunken kiss me! I was happy at least she waited until finished doing the song, but you know, consent is sexy.
Do you get hit on a lot? That’s interesting. Until
recently, no. But now, as David, people seem more sexually aggressive with me. I had one woman come up behind me and grab my chest, something she’d never done before. I guess she thought since I identify now as male that it was open season. And older gay men are a lot more aggressive physically.
What jazz artist in Philly would you leave the house to see? Denise King, even though she’s mostly in New York now, Geri Oliver and Jeannie Brooks. There are a lot of vocalists at Ortlieb’s who I love to listen to and play with. I’ve learned so much from the different musicians there; it was better than school!
What’s an unusual fact about you? [Laughing] I can’t drive! I’m 44, lived in Philly all my life, and I can’t drive.
That has to be a pain going out to New Hope so often. Yeah, it’s a matter of trains, Lyfts or getting rides.
What’s the farthest you’ve traveled? Trinidad. I did a show there with the vocalist Jakeya. We still work together on occasion; I just did a show in New Hope with her yesterday!
Random question: what were you like as a kid? I was into boxing and karate. My uncle Daryl Underwood was a boxer and karate master, and he wanted me to learn how to take care of myself. I wanted to be a jock, but that didn’t work out so well. My dad was afraid I’d mess up my hands. I was a fat kid. I was a tomboy too, but I spent a lot of time at the piano figuring out music. Not just the piano, there was a full drum set, there were guitars, all kinds of instruments and me and my two sisters would play pretend band. They both sing as well. My sister, Rhonda Underwood, has a song available on iTunes right now, and my other sister Veronica sings with the Heritage Choir. They were just at the Kimmel Center for the Soulful Christmas concert.
Any superstitious rituals? I have to show up to any gig 45 minutes to an hour before I go on. I don’t care if I’ve played there every week for 10 years, I have to show up super early and check everything out.
And last question, living or dead, who would you want to do a duet with? Oh my god, Stevie Wonder, my all-time favorite. What a sweet soul, and it comes out in his music; it’s so pure.