Writing  by Gia Miller

Photography by Justin Negard

When Ian Hendrickson-Smith (a.k.a. Uncle Cheef – a college nickname that stuck) was a high school sophomore in State College, PA, he rebelled against his parents by buying a saxophone. Already a serious musician, Uncle Cheef practiced the flute eight hours a day, and his grades were suffering. His parents told him he needed to spend more time studying and less time playing music.

“I had this big event coming up, and my parents saw that I was failing everything,” he remembers. “They locked up my flute so I could focus on my grades. I was pissed, so I started mowing everyone’s lawns in the neighborhood and used the money to buy a saxophone.”

Uncle Cheef, who owns the eponymous jazz club in Brewster, got lucky – he bought a college student’s alto saxophone that turned out to be a “gem of an instrument,” and he was hooked. During high school, Uncle Cheef also played in a heavy metal band called Patendeon and a jazz fusion band called Electrolysis. He played guitar, bass guitar, drums, piano and harmonica. But he fell in love with the saxophone.

“Saxophone was the last in my bag of tricks,” he says. “Once I got a saxophone, I put most of my other instruments away.”

Introduction to music

Uncle Cheef, who lived in New Orleans until he was 10 years old, picked up his first instrument in the fourth grade. He, along with the rest of his class in Charlottesville, VA, had to choose an instrument. He chose the drums, but his parents said no.

“I was a punk and reactive, so I said, ‘Fine, I’ll play the flute,’” he remembers. “I was the only boy playing the flute, and I kind of quickly realized it was cool. While all the dudes were sitting back there with the trumpets and drums, I was hanging out with all the girls.”

But his first couple of lessons didn’t go so well. He couldn’t grasp the concept of blowing into the instrument while moving his fingers, and he was really embarrassed. That embarrassment quickly turned into determination.

“I decided that I’m just gonna crush it instead,” he says. “I dove into it as hard as I could, and by the end of the first month, I was already practicing two or three hours a day. I was just really into it.”

He and his family moved to State College before he started high school, and he began working with a private flute teacher who changed his life.

“I had a very dedicated and amazing flute teacher; I got really lucky,” he explains. “She was a flute player in the New York Philharmonic, but she married a nuclear physicist, and they moved to Pennsylvania. She was, by far, the best teacher I’ve ever had, and she got me very focused and very dedicated very quickly.”

Before his parents locked up his flute, Uncle Cheef was playing 30-minute concertos and had performed with the Nittany Valley Symphony several times. One thing led to another, and she introduced him to jazz music.

“She started handing me records,” he says. “And the very first record she handed me was this Cannonball Adderley record called ‘Something Else.’ I still have the exact album, and it’s still my favorite record, hands down. A switch went off when I heard that record for the first time, and I decided I wanted to get a saxophone.”

Uncle Cheef played that revenge saxophone through college (he earned a full scholarship to Manhattan School of Music, where he received a bachelor of arts degree in jazz performance) until “a very reputable repairman in the city destroyed it.”

A series of firsts

After graduation, Uncle Cheef signed a nine-month contract and immediately went on the road with the Glenn Miller Orchestra. He played nine shows a week, essentially living and sleeping on the tour bus, and after three months, he moved on.

“I got called to play with the Charles Mingus Big Band,” he remembers. “My college roommate was one of their trumpet players, but I had no business being in that band. It was full of legends, and I was just this little squirrely white dude in the middle, but it was great. Although I did get my butt kicked, and I even got threatened. People pulled knives on me; it was intense. They’d say things like, ‘Play that again, and I’ll kill you.’”

Throughout his 20s, Uncle Cheef played at various clubs and had steady gigs here and there – he was making ends meet, but it was what he calls “a minimal existence.” His first major gig was with Sharon Jones and The Dap-Kings when he was 28 years old.

“I subbed in the band for about a year, whenever the other saxophone player would flake out,” he remembers. “And then there was a European tour that I was splitting with the other saxophone player. I was going to do the first three weeks, and he was going to come in and finish the tour. When I got home, they called me and asked me to come back. The other guy basically said, ‘Yeah, I’m not coming.’ So I went back to Europe, and they told me, ‘It’s your gig now.’ And that was that.”

Typical tours ranged anywhere from six weeks to two months, and he estimates they worked about 300 days a year. He traveled to Europe with Sharon Jones approximately 20 times.

Around the same time he became a permanent member of The Dap-Kings, Uncle Cheef’s first record was released. It was called “Up in Smoke,” and it was made at a popular Upper West Side jazz club at the time called Smoke, where he played on Wednesday nights when he was in town.

“I originally thought I would name every record I made after a Cheech & Chong movie,” he said one recent evening at his Brewster club. “I did it for the first, and my second album is called ‘Still Smoking,’ but I gave up on it by the third. It was fun, though. I had my fun.”

It was shortly after releasing his first album that his parents finally accepted his career path, and he began believing that he could actually make a living as a musician.

“That was the point where I thought, ‘Okay, I think I’m going to be able to make this work,’” he remembers. “I still didn’t have health insurance, and I was still living hand-to-mouth. The Sharon Jones gig was 100 bucks a night in Europe, and while they paid for all the incidentals, like travel, sometimes there would be eight of us in one hotel room.”

Around that time, while playing at The Cellar Jazz Club in Vancouver, he struck up a conversation with a bartender named Jenny Larisey.

“I asked her if she could tell me where I could buy pantyhose,” he remembers. “I was recording the band, and I needed to make a pop filter for a microphone, which you can do with pantyhose and a coat hanger. So, she told me where to go, and I brought back some lip chap for her and the rest of the staff.”

“He was so sweet to everybody, and we hung out afterwards,” says Larisey.

They continued to talk, and Larisey eventually moved to New York. After dating on and off for 10 years, they married in 2014.

Making a name for himself

Being a member of The Dap-Kings helped Uncle Cheef’s career take off.

“The trumpet player knew Mark Ronson from high school, and one day Mark called him to say, ‘I need horns on something,’” Uncle Cheef explains. “So, the three of us in the horns section went to Mark’s studio. He was putting a record together called ‘Versions,’ which is the record with Amy Winehouse’s ‘Valerie,’ on it. Then, he started using us for other stuff, and we invited him to the now-defunct Dap-Kings studio in Bushwick to record with us. Soon, he was coming once every other week. Mark would show up with a singer, and we would make a whole record. So, we did a Lily Allen record, an Amy Winehouse record – lots and lots of records. Amy was just one of the many records we made, and then that blew up.”

Uncle Cheef, along with The Dap-Kings, toured with Winehouse on her two U.S. runs. They performed on various late-night shows, like Letterman, and even at the Grammy Awards. That was Uncle Cheef’s first Grammy performance, and it was the year Winehouse and The Dap-Kings won a song of the year (“Rehab”). Winehouse also won four other awards that night.

Since then, he’s performed with countless celebrities, including Lady Gaga, Ed Sheeran, Bob Dylan, Al Green, Bruno Mars, Lily Allen, Dr. Lonnie Smith, Sturgill Simpson, LL Cool J, Run-DMC, Mofro and Vicentico Valedés. He’s also played at the Grammys several more times, and he’s won five Grammy Awards for his work with Valedés, Sheeran, Simpson, Ronson and, of course, Winehouse.

“When you do those gigantic shows, it’s nerve-racking the first couple of times,” he explains. “But I just did it recently, and now it kind of feels normal.”

Steady work

In 2009, Uncle Cheef was knee-deep in plans to open a jazz club in Brooklyn with a business partner and several investors. It was the second jazz club he’d planned, with the first being in Charlottesville several years before (it turned out not to be the best location for a jazz club). And then he got the call.

“It was six in the morning, and my phone rang,” he remembers. “It was a 215 number, so I knew it had to be Philly. I picked it up, and it was Rich (Nichols, The Roots manager at the time). He said, ‘I got a gig for you. You’re not gonna like it; it’s not really that great.’ And he was right, because for the first five years, they didn’t pay well. They make you go through a little bit of a hazing for five years. And then you can renegotiate.”

The gig was to be the saxophone player for The Roots, who had just been tapped as the new band for The Tonight Show when Jimmy Fallon took over as the host. Uncle Cheef originally met Questlove, the leader of The Roots, when he was part of The Dap-Kings.

“They’d come to The Dap-Kings’ annual picnic in Philly, which was really a music festival,” Uncle Cheef explained. “It’s grown into this massive three-day festival, but it used to be in a parking lot on the edge of Philly. We did a fair amount of stuff with them over the years, and when the Amy Winehouse record came out, Questlove showed up to a lot of those gigs. After one gig, he said, ‘Hey, I’m working on this Al Green record; do you guys want to play?’ So, we did the Al Green record with The Roots. Rich Nichols, may he rest in peace, was in the studio for every single session, and we really hit it off. So, I guess he just remembered me. When Jimmy Fallon took over The Tonight Show, Lorne Michaels insisted that The Roots add horns; it wasn’t their choice. The network told them they had to add a horn section.”

Michaels’ reason, according to Uncle Cheef, was because “horns had announced the arrival of kings for years.”

Uncle Cheef said yes to the gig and put his jazz club plans on hold. The Roots also hired Dave Guy, the trumpet player for The Dap-Kings.

Today, The Tonight Show is just one of his gigs. Uncle Cheef also regularly works with music and movie producers, writing and performing music for albums and scores for movies.

“I wouldn’t say I’m composing for musicians; I’m not a songwriter in that sense,” he says. “It’s very abstract. For example, I’ll walk into a studio never having heard a song, and they’ll ask me to craft something because they have no idea what they want. That’s why I get called. It’s up to me to know what will create the type of effect they’re looking for. I need to know if this section needs to push, if that needs to be padded, or if this needs a melody.”

“Other times, they’ll write the song with something in mind,” he continues. “Sometimes they’ll leave spots open and tell me they need a horn section right there, or this part needs an anthem or whatever. It’s an infinite variety.”

It’s a similar request when he works on movie soundtracks.

“A year and a half ago, filmmaker (and singer, songwriter, music producer) Jeymes Samuel put out a movie called ‘The Harder They Fall’ on Netflix, and I did a lot of work on the soundtrack,” he says. “I did all the horn arranging, writing and recording. I’d go in there with the trumpet player, and we would create two passages together, then I’d add in the alto flutes, regular flutes and clarinets.”

His preference is to record at his home studio because that’s where his horns are kept. However, since he now lives in Brewster, and traveling into the city with around 20 musical instruments is quite challenging, he also keeps a set at 30 Rock.

The third time’s the charm

During the pandemic, Uncle Cheef and Larisey, his wife, were debating their next step. They’d moved to Brewster in 2015, but there wasn’t much to do. They were considering relocating to Brooklyn or opening a jazz club near their current home.

“We decided to kick some tires around and see what was available in Brewster,” he remembers. “We found a great space where Bull & Barrel used to be, and we got to work.”

In May 2023, after an extensive renovation (Larisey built all the tabletops and bar shelves herself), Uncle Cheef finally opened his jazz club, and it was perfect timing. The writers’ strike forced The Tonight Show into reruns, so he wasn’t commuting to and from the city daily. Although the plan was for Larisey to manage day-to-day operations, he joined her at the club almost daily.

“This was the last thing on my personal bucket list in terms of career moves,” he says. “I wanted to tour. I wanted to make a bunch of records. I wanted to get good at my craft. I wanted to become a good engineer and a good designer. I pretty much checked off most of those boxes, and the club, the club was the last thing.”

Originally, they planned to call the club Bluebird Social, but a conversation with Tarik Trotter, known as Black Thought, changed his mind.

“He’s my go-to for coolness – if it’s not cool, it’s not gonna get past him,” Uncle Cheef explains. “So, I told him the name, and he said, ‘All right, all right. I don’t care what you call it. It’s always gonna be Uncle Cheef’s place to me. And I’ll kill you if you don’t call it that.’ So, I decided I’d rather not die, and we named it Uncle Cheef.”

They were busy from day one, with a mix of musicians and friends from the city, along with many new faces who have now become regulars. The club is open evenings Wednesday through Saturday and Sunday morning for a jazz brunch. All ages are welcome, and he sincerely encourages parents to bring their children.

“Seeing live music altered the course of my life,” he says. “I think it’s important to allow children to be in an adult environment where they can be so close to live music and even have the chance to talk to the artists. It can be what makes them pursue music.”

Similarly, the atmosphere is friendly, the food is designed to be shared and the drink menu was created by one of the top mixologists in the area, Nikki Stein. And, of course, there’s the music. The club is filled with notable musicians from Manhattan and nearby towns, including Uncle Cheef himself from time to time.

“I want to provide a cultural oasis,” he explains. “That’s ultimately what we’re about. We didn’t get into it to make money; we saw a void in an area where it seemed like a lot of people would appreciate what we’re putting out. And I want to keep making it better and better, including bringing in more national acts, enhancing our level of service and making things nicer and nicer as we go.”

This February, you can see jazz performer, composer and Katonah resident Andromeda Turre on February 17, and Uncle Cheef will celebrate his 50th birthday from February 21 to 24 at his club. Although he wouldn’t reveal who will perform during his days-long celebration, he recommends buying tickets early.

This article was published in the January/February 2024 print edition of Connect to Northern Westchester.

Hidden Inside

Uncle Cheef infused several personal and meaningful elements into his live music venue.

It’s always 10:30.

During college, his apartment was “the party apartment,” and he never wanted the party to end. One day, he set all the clocks to 10:30 so when guests looked at the time, they wouldn’t know how late it really was….until the sun began to rise.

“There are about 20 clocks in the club, and they’re all set to 10:30 to remind me not to lose sight of that naively optimistic young man,” he explains. “I like that dude, and I don’t want to get old and crusty and lose sight of that. It’s my personal reminder.”

Tip the breadbox.

“Entertainment is always foremost in our mind,” he says. “I was trying to think of a fun way for guests to tip the band. I didn’t want to walk around the house with a bucket. So, the breadbox is funny because bread is what musicians call money. And I named him Philip – it’s an obvious joke: fill up the bread box.”

Birds flying high…

There are stained-glass birds inside birdcages throughout the club, and they serve a dual purpose. They represent the Eastern bluebird (the New York State bird), and they’re an homage to saxophonist Charlie Parker, whose nickname was Bird.

“The cage doors are all pinned open, so the birds aren’t caged in,” he says. “Jenny’s father is a stained-glass artist, so he made them for us. And if you can tell us exactly how many bluebirds are in the club, we will pay for your evening.”

Heroes and sponsors

“I commissioned my friend Andy Ward to draw people that either inspired us to open the place or had a direct hand in opening the place,” he explains. “Sharon Jones is up there, and so are Dr. Lonnie Smith, Black Thought, Quest Love, Duke Ellington, Billie Holiday and my investors. Ward lives in London, so once he completed the piece, he sent me the files, and I printed it here.”

Name that sculpture.

Inside the club, to the left of the doors, there’s a human-like sculpture of musical instruments, featuring a bass drum and trumpets. It’s been a dream since Charlottesville.

“It was part of my original business plan,” he explains. “It was always in the game plan to build a sculpture made entirely out of instruments. I didn’t know what his name was – he had to exist first, and then I named him. But I won’t share his name – people must guess. The one clue I’ll give you is ‘a cousin of Pixar.’”