The new Lucille! is a leap forward for Jason Stein, who began by taking a leap—he picked up the bass clarinet at age 22 and played his first show with it that week. Credit: Shea Whinnery

On December 4, 2015, Chicago bass clarinetist Jason Stein played his first arena show, at the BMO Harris Bradley Center in Milwaukee. He knew that the 14,000 people in the audience hadn’t come to see him, even though he’s toured on several continents and earned acclaim in the New York Times and DownBeat magazine—free jazz isn’t a lucrative racket. For Stein and the musicians who share his circuit, a crowd of 50 in a cozy bar like the Hungry Brain counts as a respectable turnout.

The star who’d filled the arena was one of Stein’s two younger sisters, comedian Amy Schumer—and that night was the beginning of what would become a regular opening gig for Stein and his long-­running trio Locksmith Isidore, with Chicago bassist Jason Roebke and New York drummer Mike Pride.

Stein was initially skeptical that fans who’d come out to see Schumer’s comedy would tolerate his music. “When we first started doing them, my vibe was to be really sarcastic and assume that everyone was bummed out that they had to listen to jazz,” he says. But his self-deprecation turned out to be unwarranted. “After a few of those, both Amy and Cayce [DuMont], my wife, said, ‘It doesn’t make sense for you to do that, because everyone seem to be having a good time.'”

Stein has been a fixture on Chicago’s jazz and improvised-music scene for 12 years, playing his notoriously unwieldy instrument with fluidity, soul, and grace. When Locksmith Isidore hit the road with Schumer, they stuck to the same repertoire—rooted in driving, swinging postbop and often enlivened with daring feats of improvisation—that they’d honed at Chicago clubs such as the Hungry Brain, the Hideout, and Elastic. As far as his bandmates could tell, Stein came to feel the same way about those stadium crowds as he did about any crowd: “There were nights where we’d be playing in a world-famous arena for 15,000 people,” Pride says, “and his stage banter was no different than when we played in front of 50 people at some creepy haunt in Vienna or in front of 15 people at a thrift store in Charlotte.”

These days Schumer is busy finishing a movie and launching a Broadway show with Steve Martin, so Stein is back on his own grind. On Saturday, he celebrates the release of the excellent quartet album Lucille! (Delmark) with a performance at Constellation, capacity 150. In most ways the big gigs with his sister haven’t changed him at all, though they have provided a degree of financial stability. “I’m living the dream,” Stein says earnestly. “It’s not that much of a dream. I can hang out with my [daughter Ida] and Cayce, I can practice a lot, and I can play whenever I want. That’s all I want.”

Schumer’s business is to some extent a family affair—her other sibling, Kim Caramele, has worked as a cowriter and producer on her TV shows—and this has meant additional opportunities for Stein too. He’s turned up alongside Schumer on TV several times: in a trio with drummer Questlove and jazz bassist Christian McBride in a 2016 send-up of an old Muppets skit for Inside Amy Schumer, in a 2016 interview on Chelsea Handler’s Netflix series Chelsea, and on a 2017 episode of Celebrity Family Feud. But he’s not interested in parlaying the connection into his own shot in showbiz.

“If I wanted to be famous, enough things have come up that I could say, ‘I’m Amy Schumer’s brother,’ and it could be a thing,” Stein says. “But I would never do that in a million years—there’s no appeal to me about that.” When he toured with Schumer, he didn’t even try to sell his records to the folks who came out, insisting that the shows weren’t about him.

Stein has never been much of a careerist. After moving to Chicago in 2005, he released a streak of solid albums under his own name, but then he decided that improving his playing was more important than building on that momentum—in 2011 he stepped away from leading bands, focusing instead on gigging as a sideman and practicing at home. The new album is his first as a leader in six years.

On the hard-swinging Lucille! Stein gets top-shelf support from reedist Keefe Jackson, bassist Joshua Abrams, and drummer Tom Rainey, and his own performances validate his decision to dedicate himself to improving as a musician. The album is a major leap forward for an artist who began by taking a leap—now 40 years old, he picked up the bass clarinet at 22 and played his first show with it that same week. The nine tunes on Lucille! include three of his own, sprinkled among bebop classics associated with Charlie Parker, Thelonious Monk, and Lennie Tristano, all of which the quartet reinvents via Stein’s deft, elevated interplay with Jackson.

Jason Stein Quartet

Sat 9/30, 8:30 PM, Constellation, 3111 N. Western,, $10, 18+

Born in Long Island in 1976, Stein was a basketball prodigy in high school (he’s six foot four), but after he graduated in 1995 he felt aimless. When he turned 18, he received a life insurance settlement that his father had left him in his will. (He’d died when Stein was 11.) The money was supposed to pay for college, but Stein used it to finance several years of drifting. In 1996 he went to Helena to join the Montana Conservation Corps; in 1997 he traveled by bus from San Diego through Mexico to Honduras and Guatemala; in 1998 he studied math and philosophy at Stony Brook University on Long Island in New York. “My grandma (not lovingly) called me the Wandering Jew,” he says.

Stein began exploring music in earnest in early 1999, after moving to Bozeman, Montana—he played jazz standards on guitar in a local band that had a weekly restaurant gig. He discovered the bass clarinet in May of that year, after he’d already been accepted to Bennington College, an unorthodox school in Vermont. (He intended to study writing when he started classes that fall.) Taken by the sound of Eric Dolphy’s horn on a John Coltrane album, he stopped at a Bozeman music shop. “I was like, ‘I’ve heard of this instrument—I think it’s called a bass clarinet. Do you know what I’m talking about?'” he recalls. The shop did, of course. After learning the proper embouchure from the owner, Stein rented a horn and took it home. “That day I learned everything I could already play on my guitar on the instrument, and I played it on my gig that weekend,” he says. “I wanted something to give a shit about, and it was a good fit. It gave me something to focus on.”

Before school started at Bennington in September, Stein made a trip home, stopping by the small apartment in Rockville Centre, New York, where his sisters and mother lived (technically they’re his half sisters—Stein’s mother remarried when he was three). “I told them I was really into this instrument, and I took it out and played it,” he says. “Amy was really sweet and started crying. I could really play, and she understood that I was really, really excited.”

At Bennington, Stein practiced bass clarinet constantly and switched his concentration from writing to music. But he felt that the school’s jazz program—whose faculty then included free-jazz greats Charles Gayle and Milford Graves—was geared toward advanced students and didn’t give enough attention to rudiments. Even though Stein was a quick study and had already taught himself a great deal, he dropped out after a semester and returned to Bozeman.

In 2000, Stein followed a girlfriend from Montana to Charleston, South Carolina, where they ended up living for a year in a friend’s parents’ house on the ocean. He began studying music at the College of Charleston, but on the recommendation of saxophonist Ben Abarbanel-­Wolff, whom he’d met at Bennington, in 2001 he transferred to the University of Michigan. In the 1990s its prestigious jazz program, led by saxophonist Donald Walden, had graduated adventurous musicians such as Colin Stetson, Matt Bauder, Stuart Bogie, and Toby Summerfield. During the three years Stein spent in Ann Arbor, he made regular trips to Chicago, where pianist and childhood friend Paul Giallorenzo had settled after finishing his studies at Northwestern.

“I remember coming in and playing some gigs at Phyllis’ Musical Inn, and I thought it was really exciting,” Stein says. He made friends with many musicians who were becoming important in the Chicago scene, among them Keefe Jackson, cornetist Josh Berman, and drummers Mike Reed and Frank Rosaly. During this time he also played with veteran reedist Ken Vandermark, and after one more relocation—to Austin, Texas, for about six months in 2004—Stein ended up moving to Chicago in early 2005, lured in part by Vandermark’s proposal to start a quartet with him, drummer Tim Daisy, and bassist Nate McBride. The group would be called Bridge 61.

Lucille! is Stein’s first album as a bandleader in six years.Credit: Shea Whinnery

Stein found living quarters for $100 a month in the old Humboldt Park church basement that also housed performance space 3030, and in 2006 he appeared on his first record: the sole Bridge 61 album, Journal. “When Bridge 61 started happening, I felt this strong sense to keep making records, doing this thing I had seen Ken and Tim and a lot of those guys doing,” Stein says.

After landing a gig at New York club Tonic in 2007, Stein put together the first iteration of Locksmith Isidore with Pride and cellist Kevin Davis. The group released increasingly strong albums in 2008, ’09, and ’10, with Roebke replacing Davis after the first; also in 2009, Stein put out an impressive solo record called In Exchange for a Process. In 2011 an earlier version of his quartet (with Rosaly on drums) dropped The Story This Time, but by then he was rethinking his modus operandi.

“I wanted to go back in the shed and play more,” Stein says. “It wasn’t something I thought about at first—you just make a shitload of records and see what happens. And after doing it for a year or two, I realized it didn’t suit me. But I was working in a lot of other bands, and that made me comfortable—because I still felt relevant or whatever, and I was still on records. I really like working as a sideman, and I love touring in other people’s bands; it’s really fun and easy as opposed to being a bandleader.” In the years since this reorientation, Stein has played on albums by several other people, including Roebke, Rosaly, Reed, trumpeter Russ Johnson, oboist Kyle Bruckmann, and drummer Charles Rumback. Not till Lucille! would he take top billing again.

For most of his time in Chicago, Stein earned his living teaching private lessons in the suburbs, and the flexible schedule this work afforded him became more important after his daughter was born in 2014. By then Amy had become a major figure in the comedy world, and she’d been pushing him to do shows with her for years—since shortly after she placed fourth on Last Comic Standing in 2007. But Stein always demurred: “I would say, ‘I don’t think that’s a good idea. What would I do? Nobody wants to see that.’ It was a running theme for a long time.”

When Schumer asked again in May 2015, it was different. “It was the first time that she proposed it where I actually knew someone who ran a venue where I could ask about doing a show spontaneously,” Stein says. “I could see it happen in my head, and it didn’t seem insane.” He called Mike Reed, who owns Constellation, about hosting a concert the following evening. This became a pattern: whenever Schumer would fly into town to hang out with Stein’s family, they’d throw together a gig a day in advance. The shows consistently sold out with nothing more than a ticket announcement—something Stein has never been able to count on at his own performances.

Still, when Schumer suggested doing a tour together, he wasn’t moved. “I thought, ‘Sounds fun—it’ll never happen,'” he says. “Touring for her at that time was still at standard comedy clubs. But then I got an e-mail from her and her booking agent saying, ‘OK, the tour is set, can you do all of these dates? They’re going to be at arenas.'” Partway through the time he spent opening for Schumer, Stein gave up teaching private lessons, not just because scheduling them had become too difficult but also because he was making real money on the road.

“I think he’s gotten a lot more outspoken and confident over the past few years, for unsurprising reasons,” says Giallorenzo, who plays with Stein in the long-running trio Hearts & Minds. “That comes across in his playing. I think doing these shows with his sister, speaking to the crowd, and generally sharing some of the spotlight with her has definitely made him a lot more comfortable in his own skin.”

Now that Stein isn’t regularly touring with Schumer, he’s returned to solidifying his own projects. The quartet on Lucille! has no current plans to tour, but he’s got other irons in the fire: next spring Locksmith Isidore will release an album on Northern Spy, this fall Hearts & Minds will cut a studio record, and Stein will soon begin working in a promising new quartet with saxophonist Greg Ward, bassist Eric Revis, and drummer Jim Black.

Stein seems genuinely content to be operating on a smaller scale again. “I’m a bass clarinetist,” he says. “There’s no ‘Oh man, now I’m doing the big time.'”  v