Swing Shifting to Jazz, Heather Masse has a Wailin' Good Time With Roswell Rudd

As one-third of the Wailin' Jennys, the most heavenly trio in folk music today, Heather Masse would be the first to admit that jumping into the jazz scene with a trombone legend is a bit like a successful comedian sharing the screen with a dramatic acting heavyweight.

The ability to improvise is a plus, but when it's time to perform, you had better deliver. And with one pure voice, Masse does just that on her latest project called August Love Song, an album of freewheeling jazz numbers, time-tested American Songbook classics and appealing originals she made with award-winning jazz trombonist Roswell Rudd.

The record will be released Friday (Feb. 26, 2016) by Red House Records, the esteemed roots label with a talented roster that includes the Wailin' Jennys, Jorma Kaukonen, Dale Watson and Pieta Brown.

An 80-year-old father of two who's been widowed since 2004 and a wife and mother who's still young enough to be Rudd's granddaughter would initially seem like an unlikely pairing. But not soon after meeting as guests on A Prairie Home Companion on Valentine's Day 2009, Rudd and Masse formed an informal musical alliance upon discovering they already were close geographically -- living about eight miles apart in New York's Catskill Mountains.

"We found a real connection musically and so when we recorded it, we decided to try to keep that energy of that sort of live (performing), just getting together, hanging out and playing music," Masse said over the phone from her home the evening after Valentine's Day 2016. "And so we did it in Roswell's living room, which is where we get together to play music. And so when you're recording in a living room and basically everything was live, it's hard to know what you're gonna get from that."

Especially when you're taken out of your comfort zone as upright bass player and most recent addition of the Jennys, the sweet-sounding roots group she joined in 2007 that includes Canadian co-founders Nicky Mehta and Ruth Moody. (The Jennys, from left: Masse, Mehta and Moody.)

Masse, a serene being with an alluring alto, knew about Rudd through one of her best friends, South Korean vocalist Sunny Kim, who had been a member of the Roswell Rudd Quartet. Invited to play at his home, Masse said it "felt really easy and natural" after only a few sessions, then she substituted for Kim on one gig "that went really well with Roswell."

With the help and encouragement of Roswell's partner and manager, Verna Gillis, they eventually decided to make an album.

Last year, it took only two days to record August Love Song, which Masse said isn't unusual in the jazz world but lightning fast compared to her previous experiences (about three weeks) with the Wailin' Jennys.

Family life and other individual projects have reduced their recording and touring duties as a group in the past few years, so during hiatuses, Masse delivered her first baby (August Loyal Duncan was born on Aug. 18, 2012) and first full-length collection of standards with a jazz veteran (Lock My Heart with Emmy Award-winning pianist and composer Dick Hyman was released on Feb. 12, 2013).

A fan of the genre since the age of 10 or 11, when she heard songs sung by Ella Fitzgerald and Sarah Vaughan on a mixtape made by her oldest sister, Masse decided to further her education by studying jazz voice at New England Conservatory after performing as a singer and pianist in the jazz band at Fryeburg Academy in Maine, a few miles down the road from her hometown of Lovell.

"I ended up kind of singing professionally with my music director when I was in high school (class of 2000) and I just really fell in love with the music," Masse said. "Singing jazz, singing the American Songbook and when I applied to New England Conservatory, my idea was to focus on jazz but it also has a really great classical program, so I was also interested in singing classical music as well. But jazz really spoke to me. Those old songs and the style of singing."

Masse, who released her first full-length solo album (Bird Song) in 2009, even decided to test herself with more "adventurous" vocals for this album, mimicking Rudd's trombone notes on Gillis' "I'm Going' Sane (One Day at a Time)" or taking off into unchartered territory on Rudd's "Winter Blues."

"I've never been a scatter, you know, a jazz improviser as much," said Masse, who still feels like "a little bit of an outsider in the jazz world" despite her credentials. "But I sort of delved into that in a way that would have normally made me feel very uncomfortable. But Roswell has a way of kind of pulling things organically out of you."

Rudd, born in Sharon, Connecticut, in 1935, has been a musical maverick since playing Dixieland jazz with his fellow Yale students in Eli's Chosen Six in the '50s. His varied career includes being voted most likely to succeed by DownBeat magazine in 1964, becoming a music teacher at the University of Maine in 1976 and creating The Incredible Honk in 2011.

With a long list of collaborators, he has traveled the world playing free jazz and avant-garde jazz, and has been associated with Gillis' Soundscape operation since 1999.

Heather Masse (left) and Roswell Rudd formed an "easy and natural" musical alliance before recording their new album. (Photo by Craig Paulson)

On his latest venture, making that trombone speak so fluently alongside such an elegant folk singer was an exercise in exhilaration.

For Masse (right), sharing vocals with one or more instruments instead of two female singers became freeing -- allowing for chances to improvise -- but still challenging.

"You have all this room to go wherever you want to go following a chord structure form of a song," said Masse, who comes out swinging on the album that also includes bursts of brilliance by Rolf Sturm (guitars) and Mark Helias (contra bass). "But if you don't necessarily get the changes right you can potentially move somewhere else. ... But I really like the balance of both because I really crave both. I really feel like folk music and singing and harmony and creating a song that's very composed and simple and beautiful is really important and what comes to me naturally through music. But then the improvisation is also a big part of who I am musically as well."

Along with classic compositions by George and Ira Gershwin ("Love is Here to Stay"), Duke Ellington ("Mood Indigo") and Dizzy Gillespie ("Con Alma"), Masse and Rudd contribute two numbers each to the 10-track album. They've tried out their material at various clubs, and performed with a number of guests for Rudd's 80th birthday show at Le Poisson Rouge in New York City last November.

"Love Song for August," the bluesy/Dixieland jazz hybrid Masse wrote last summer for and about her son, now 3 1/2 years old, not only fits nicely into this collection (see her recent A Prairie Home Companion performance below) but also represents the meaningful musical relationship made by this mellifluously mod couple.

With Gillis at his side, Rudd (left) did more than make a record with Masse. They turned her son August into a jazz aficionado.

"Roswell and Verna gave him a trombone for his second birthday and he was practicing all day every day. He's not really into that so much these days but for a good six months it was kind of all he did and talked about," said Masse, who previously wrote the Jennys' "Across the Sea" for her husband Ian Duncan. "(August) likes to play my bass but not as much as the trombone. There's something about the breaths that it takes. (laughs)

"August also has been on some Wailin' Jennys tours as well, so he's been around a variety of instruments but for whatever reason he's really focused in on the trombone."

Since Masse said she rarely listens to her own music at home, jazz is cool for a 3-year-old these days, though August likes "some folky stuff" and went through a phase where he played 30 different versions of "Hush Little Baby." So he -- and folkies of all ages -- should be especially pleased to hear that his mom will be going back to work soon with the Wailin' Jennys, whose last album was the Juno Award-winning Bright Morning Stars released in 2011.

"We haven't recorded anything," reported Masse, who added that a new album might still be at least a year away. "We're just in the very early stages. So I'm really looking forward to that. We're gonna be getting together and just start working on some new material for whatever the new record will be. And that's really fun to really get a song to a place that feels just right arrangement-wise."

With the hope of bringing "the jazz and the folk worlds together a little bit more," Masse has new and old songs ready to offer and, she added, "We kind of know right away after somebody plays you a song, if it's gonna be a Jennys song because there's something that's really unique about it in that we all know right away if it's gonna work."

Until then, she'll continue making guest appearances on A Prairie Home Companion during Garrison Keillor's final season (saying "I'd love to be a part of it" when Chris Thile take over), and perform occasionally with Rudd in New York City and closer to home.

Just like with comedy, music's a matter of timing, and whether she's singing jazz or folk, a disciplined Masse takes her craft seriously. Once in awhile, though, playing it by ear by acting on your instincts feels just as good.

Wailin' Jenny publicity photo by Art Turner. Concert photo by Michael Bialas.

Heather Masse (with Rich Dworsky and The Mardi Gras Boys) sings "Love Song for August" on Feb. 13, 2016, for A Prairie Home Companion: