The Cleveland native sat down with Billboard before his Thursday night residency at Gramercy Park Hotel’s legendary Rose Bar to tell us about how he got started, gigging with some of music’s biggest legends and landing a dream residency.
Tell us about your musical background.
I always loved all kinds of music. Growing up as a trumpet player and trying to work in the music industry, you had to be versatile and sort of “get in where you fit in.” I think about that every time I play with any band. You’re there to make the band, as a whole, sound better. My musical tastes run from Thin Lizzy to Dr. Dre — everything. I love country music and blues artists [like] Willie Nelson and Faron Young, and I also really like Beck and Frank Zappa. I like anything that’s “good music.”
New York City’s music scene is one of the hardest to break into. How did you do it?
It’s so hard to make it in New York, but I knew that if I never moved here, I would never make it [in the industry] if I stayed in Cleveland, where I’m from, or in Cincinnati, where I went to school [at Cincinnati College-Conservatory of Music]. I moved here in 2003 with $500, a U-Haul, and a first and last month’s security deposit on a tiny apartment, and just started cracking away. I played as much as I could, responding to ads on Craigslist, playing with all kinds of different bands. I waited tables, I bartended, did everything to [make some extra money].
Getting to [this residency at] the Rose Bar wasn’t easy. I started off doing a jazz brunch residency with my band every Sunday at Jules Bistro, then we had our long-standing gig playing a burlesque show at Duane Park. I figured, if I wanted to get people to come out to see me play, why not get the most beautiful and talented burlesque dancers in the city to put on a show that would make jazz music a little more accessible to the masses? We then landed a residency at the Oak Room in The Plaza Hotel, but that closed in 2011 — we actually recorded an album there the last night they were open. Shortly after that, [the programmers from The Plaza helped us] get the gig here at the Rose Bar, and we’ve been here since 2012. It’s a wonderful thing.
So tell us more about the residency at the Rose Bar.
The creative director here at the Rose Bar was looking for something — they didn’t know what they wanted because they hadn’t really had music here yet. We started just on Thursday nights to fill that 8 p.m. to 10 p.m. slot — after happy hour but before the parties — and try to give people a little something different. It took about two months to pick up, but now it’s packed every Thursday throughout the year, and they added us on Tuesday nights too. It’s great to have a place like the Rose Bar where we can try new things in front of a live audience and get immediate feedback. We get to change up our songs, bring in regulars and newbies and find different ways to engage with them.
When you say “we,” are you referring to longtime band members?
Yes! I’ve been playing with the same guys for a long time. The piano player since 1999, the tenor sax player since 2001, my drummer since 2006, and our bass player is “new,” but he’s been with us for two years already. I’m loyal not only to venues and the people who work for the venues, but also to the band members who’ve stuck it out with me all this time. I need that consistency so we can grow our sound and turn it into a brand. We don’t have to change the content to make it accessible to different demographics. We just love playing for people.
One of your most formative relationships in your career has been your friendship with Lady Gaga. How did you meet and start playing with her?
It’s been a very humbling experience. I’m very lucky, very honored. Moving here from Cleveland, I just wanted to play music, and getting to that level has been an amazing journey, but it was definitely hard to get there.
Gaga and I knew each other from way back in my bartending days at St. Jerome’s; she was a go-go dancer, DJ, promoter — she did everything. She started visiting [my band] when we had our residency at the Oak Room, and was really impressed with what we were doing, so she would sit in every once in awhile. After that, she started calling us for little things here and there. She flew me out to London to play for the big BBC Radio 1 weekend and I blew solos while she changed costumes.
She met Tony Bennett at the Robin Hood gala; I remember he came backstage and said, “We should do a song together!” so they recorded “Lady Is a Tramp” and asked my band to play on it. After that, we did a couple other performances and it kind of snowballed. We were so honored when they asked us to play on the [Cheek to Cheek] record, and then we got to go on the tour with Tony’s band. We played together and separately, set up side by side on the stage, and it was an amazing experience.
It keeps going too — Danny Bennett, one of Tony’s sons, is the head of Verve Records, and signed my band because of what he saw from us on the tour, while his other son, Dae, produced one of our records and is currently producing the one we’re working on. Gaga is an exceptional performer, and an incredible musician and songwriter — that’s what I’ve always liked about her. She writes all her own stuff and internalizes her music as her own, even when she’s doing her covers. To be able to take the jazz standards that have been performed by artists all across the board for the past 50 or 60 years and to make it her own, that’s what I love when I hear musicians.
You also played with Stevie Wonder. What was that like?
Playing with Stevie [Wonder] was absolutely insane. I played with him for Tony [Bennett’s] private 90th birthday party. I was already slated to play a 90-minute set with Gaga [for that party] — and we were actually laying down tracks for Joanne at the time — and Stevie asked if we would hop onto his set; he played maybe four or five songs. I mean, thank god I played in a wedding band when I was a kid so I already knew his music. It’s some of the hardest music to play as it is, but he threw some curveballs, didn’t play things in the original keys; it was incredibly challenging. To be able to play with him, to meet him and talk to him, and for him to dig what my band does, it was incredible. Guys that big, they don’t have to say anything to me or my band. For all these people — Gaga, Stevie, and Tony — it really is a family affair for them. That’s key for this business. People sometimes act like they’re too big, or too cool, and I’ve never seen these guys act like that. That’s why they’ve been able to stay in the industry for so long. They stay humble, they always push themselves to be better, they treat people with respect.
What should people expect when they come to see one of your shows?
We do originals of mine — both instrumental and with vocals — as well as jazz standards, since those fit in so well with what we do and that repertoire is so huge. We can take standards or covers and arrange them to be something completely different than the originals, which makes things fun for us and our audiences. We want to make songs uniquely ours. We never want to change our content or dumb it down; we can still play challenging music and make it engaging for our audience.
How do you balance playing the traditional music you’re known for and incorporating some more of the contemporary music that is more recognizable?
The way I see it, so many of the categories that musicians are put in are because they have to be marketed a certain way, in order to be “sold” to their audience. I think the best way to balance the struggle between traditional and contemporary music is to not think about it too much, and just play music. You have to put in the same heart and authenticity into whatever you play. If you stay true to you and to the music, the people who are listening will connect with it.