The Wailin' Jennys
Photos: Michael Bialas

The Wailin’ Jennys Keep Making Sound Decisions After 20 Years of Sweet Songs

For a trio that’s been around as long as the Wailin’ Jennys, it’s time to commemorate this major anniversary and honor them with a career retrospective.

The Wailin’ Jennys, one of North America’s best singer-songwriter trios regardless of gender or genre, have a history of recognizing their time together. Still, even though I’ve covered this roots-grounded group many times and have conducted individual interviews with co-founders Ruth Moody and Nicky Mehta, along with most recent addition Heather Masse, their social media post on 19 January caught me by surprise. 

“We don’t know how it happened but we turned TWENTY today! We feel immensely grateful to still be singing for you all — we can’t thank you enough for your ongoing support and love. Here’s to another 20 years music! With love and appreciation, The Jennys.”

There’s no time like the present to honor the Jennys, three unrelated artists who have established a sisterly bond with a brand of North Americana grandeur. While occasionally marking special celebratory events on their calendars, and producing what might be the most beautiful three-part harmonies on this continent (if not the world), they rarely raise their voices to spread the word about this triplicity of talent. 

So let’s try and help do it for them. Through past reviews, phone and email interviews, and articles I’ve written over the years, many of their accomplishments will be acknowledged in this career retrospective as they start to wind down this 20th year of existence with a November tour through Montana. And after seeing them fall in love with the Centennial State — from one of their opening Colorado shows (at Loveland’s Rialto Theater in 2011) to their most recent run that included a first-time stop at Boulder’s Chautauqua Auditorium (on 30 September) — I can attest they’ve never sounded better. But let’s start from the beginning.

The Wailin' Jennys
The Wailin’ Jennys at Chautauqua Auditorium in Boulder on 30 September: From left: Nicky Mehta, Ruth Moody, and Heather Masse

Birth of a Band

Winnipeg, Manitoba’s Moody (the soprano) and Mehta (the mezzo), initially started performing on Canadian soil with Calgary’s Cara Luft in 2002 shortly after they appeared separately as part of the 2001 Winnipeg Folk Festival’s lineup.  

Mehta, who plays guitar, drums, harmonica, and ukulele, and made her solo album debut in 2001 with Weather Vane, remembered in our 2017 phone interview for articles in the Huffington Post and No Depression: “Ruth had approached us … just to get together and sing together. So we did that. We sort of thought, ‘Let’s put a show on and just have fun with this. And then we just happened to mention it to our friend [John Sharples] who had this little guitar shop [Sled Dog Music], which was right next to my house at that time. … We advertised the show and it sold out. It wasn’t a big guitar shop, so it wasn’t surprising that it sold out. … We were fairly established in Winnipeg as solo artists and Ruth had been in Scruj MacDuhk [as the lead singer of a five-member band of Canadian folkies that included Leonard Podolak and Jeremy Penner], so she was fairly well known. … I remember my mom gave us a standing ovation, and she had never done that for one of my shows. (laughs) So I thought, ‘Hmmmm, maybe there is something to this.’” 

The Wailin’ Jennys, one of the funniest (and punniest) names for a folk trio (thanks to Sharples’ suggestion), released their first two full-length albums — 2004’s 40 Days and 2006’s Firecracker on Red House Records, thus beginning a fruitful relationship with the St. Paul, Minnesota, indie roots label. Each member basically split up the songwriting duties. Moody’s “One Voice”, “Beautiful Dawn” and “Glory Bound” are Jennys’ classics that still find their way onto set lists today. Mehta’s “Arlington”, which may be one of the most beautiful-sounding selections ever written about death — and what she told me was the “best song that I’ve written for the band” — is a mainstay in their live show, while Firecracker’s “Begin” and “Starlight” remain heartfelt, enduring ballads.  

Yet it wasn’t until New England’s Masse (the alto and upright bassist) joined in 2007 that the Jennys officially became the band we now know and love. Her early contributions to the collective’s noteworthy collection included two from 2011’s Bright Morning Stars — “Bird Song” (the title cut of her 2009 full-length solo album debut) and “Cherry Blossom Love”.

Admittedly more of a fan of rock music than folk, roots, bluegrass, or country while growing up, I didn’t really become aware of the Jennys until after starting to write and interview artists in 2008, first for an online outlet called Blogcritics. And I indirectly became familiar with Moody and the Jennys through my 2010 Huffington Post interview with Aoife O’Donovan, who was with Crooked Still at the time. 

A couple of Jennys lineup adjustments along the way included finding a replacement for Annabelle Chvostek, who left the group in 2007. Moody reached out to O’Donovan, who recommended Masse, “one of my very best friends”, the Crooked Still leader pointed out since they went to college together at the New England Conservatory of Music.

Moody, the Australian-born artist who plays banjo, guitar, accordion, bodhrán, and piano, grew up singing with her two sisters in the Wolseley neighborhood of Winnipeg. Releasing The Garden, her full-length solo album debut (that topped by best of 2010 list for No Depression), she remembered in our HuffPo interview that summer: “I called [O’Donovan] because she’s a great singer and I knew she would know what we needed and right away. She was like, ‘Yep, I got the perfect person.’ And it was just amazing. It just worked out so well.”

Ruth Moody
The Wailin’ Jennys’ Ruth Moody smiles with banjo in hand.

Getting Masse

On 23 March 2022, the Jennys returned to the bathroom inside World Cafe Live in Philadelphia, where they gave Masse a “mini-audition” in December 2006. “We sang [the Hank Williams cover] ‘Weary Blues [From Waitin’’] together and I guess the rest is history!” they posted on social media, preceding it with “Here’s a little bit of Jennys trivia no one asked for.” 

A New Englander born and raised in Maine but now living in Taos, New Mexico, with her husband Ian Duncan and two young children (ten-year-old August Loyal and three-year-old Ida Rose), Masse also has worked on various projects since her first solo album. The jazz aficionado has performed separately and with the Jennys on Garrison Keillor’s A Prairie Home Companion, and collaborated on albums with two jazz musicians — pianist Dick Hyman (2013’s Lock My Heart) and late trombonist Roswell Rudd (2016’s August Love Song). She wrote the bluesy/Dixieland jazz title cut to the latter album as a sweet salute to her son. 

A singer and pianist in the jazz band at Fryeburg Academy near her hometown of Lowell in Maine, Masse recalled getting started in the business before studying jazz voice and graduating from the New England Conservatory of Music. 

“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 in our 2016 phone interview for HuffPo. “Singing jazz, singing the American Songbook … 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.”

Ruth Moody
Ruth Moody brings her soprano, guitar, and more to the Wailin’ Jennys.

Arriving in Colorado

The 3M sisterhood-good combination of Moody, Mehta, and Masse clicked, first with the 2009 release of the 18-track Live at the Mauch Chunk Opera House album, recorded in Jim Thorpe, Pennsylvania, with Penner on violin and mandolin. Other memorable, more personal moments occurred that year, too. Masse got married, while Mehta and her partner Grant Johnson welcomed twin boys Beck and Finn in July.

Two years later, only days after the release of Bright Morning Stars (which reached No. 1 on Billboard‘s bluegrass chart), Colorado brought us together when I first saw the Jennys perform live before a sellout crowd at the Rialto Theater in Loveland on 13 February 2011. On a night when love was in the air and seven tunes from the album about deep devotion and emotion were performed, Moody tried to get the crowd in the mood in a town known as “America’s Sweetheart City”. 

Just hours before the actual holiday, she stated, perhaps with a good-natured nudge, “We have the feeling that you’re kind of romantic around these parts. That’s the sense we got walking around. We also thought it was kind of funny that we’re in Loveland on anti-Valentine’s Day.” 

Such tinges of wry humor have become part of their live act that by then had added Moody’s brother Richard on viola, fiddle, and mandolin, after Penner’s decision to take a music break. The beginning of a beautiful friendship between the Jennys and Colorado also turned into a torrid love affair. The Centennial State frequently is included on their itinerary. Hiatuses involving family time (Moody and partner-musician Sam Howard celebrated the arrival of their baby boy Woodson in November 2016) and solo projects have taken them off the road for extended periods, though.

Nicky Mehta
Singer-songwriter Nicky Mehta beats the drums for the Wailin’ Jennys.

With an 11 March 2015 date at the 850-seat Boulder Theater, the Jennys finally made their debut in the bustling college town blessed by the magnificent Flatirons backdrop. In our email interview for HuffPo, Mehta made sure outside forces wouldn’t threaten the Juno Award-winning band’s longevity. 

“I think we’ll stay together as long as we possibly can — as long as we can continue to balance our other priorities with the needs of the group, I can’t see why we’d stop,” wrote a hands-full Mehta, who at the time was still hoping to finish a second solo album years after Weather Vane earned a Canadian Independent Music Award nomination in 2002. “We’ve learned over time how to approach it in a healthy way and have tweaked as we’ve gone. I think we’re working better together now than we ever have, in fact. We’re having more fun now that were not touring 250 days of the year. We’ll only do it as long as we’re having fun and our fans are still with us, of course. Our fans are so loyal but we never take that for granted — we try and make sure we’re giving them enough to have them stick around for the long haul.”

Nicky Mehta
A dedicated activist, Nicky Mehta also plays guitar, ukulele, and guitar.

Turning 15 in 2017

They gave Jennys fans plenty of reasons to celebrate in 2017, noting their successful existence together with another tour in support of the long-awaited album Fifteen which was released on 27 October. The record of nine favorite cover songs produced by the Jennys pays tribute to an eclectic mix of artists. (It also was a No. 1 Billboard bluegrass hit.) The band’s fifth full-length album but first in six years commemorates their 15-year anniversary, but there’s another significant milestone worth mentioning — 10 years since Masse joined the group. Ever the optimist, she was working on songs old and new for a new Jennys album as early as 2016 while wanting to see “the jazz and the folk worlds together a little bit more,” the band’s youngest member noted. “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.” 

The group settled on the covers album, though, creating just enough of a “pocket of time” during February 2017 to record it in five days in a Victoria, British Columbia, studio, Mehta recollected. 

It proved to be an excellent year for Wailin’ Watchin’, too. Coloradans got an early treat when the Ruth Moody Band made its first Denver appearance, at Swallow Hill’s Daniels Hall on 23 June. She and a group that included Richard Moody, guitarist Adam Dobres, and her bass-playing partner Howard performed many lovely songs from her solo career, including the title track to The Garden, along with “One Light Shining”, “Pockets”, “Trouble and Woe”, and Bruce Springsteen’s “Dancing in the Dark” from These Wilder Things. That 2013 solo follow-up LP included guest appearances by O’Donovan, Mark Knopfler, and Jerry Douglas. Another glistening live cover they did that I wish the Jennys would eventually incorporate into their shows was “In My Life”, my favorite rendition of a Beatles tune done by any artist. 

During an August stop at the Rocky Mountain Folks Festival in Lyons, Colorado, I finally got to meet and casually chat with all three jubilant Jennys near the guest dining tent behind the stage, where Moody’s nine-month-old son was the center of attention. Two months later, though, before their 19 November sold-out return to the Boulder Theater, the new mom felt happy to discuss the upcoming Fifteen but somewhat sad talking about one particular cut — “Wildflowers”, written by the late, great Tom Petty. 

“That was actually the first song that we knew we wanted to record on the record because fans have been asking for years for us to record that ever since we started playing it in our shows,” Moody shared during our phone interview for HuffPo just 17 days after Petty’s shocking death on 2 October 2017. “It’s so strange when these artists that are — it feels like they’re part of your life because their music has been with you for so long — are suddenly gone.” 

Heather Masse
Heather Masse plays upright bass for the Wailin’ Jennys.

Lyons’ Share of Approval

Since the title cut from Petty’s 1994 album has been an integral part of the Wailin’ Jennys’ shows, its inclusion on Fifteen undoubtedly upped the requests. An appreciative Folks Festival audience got a sneak listen on 20 August that year during the trio’s first appearance in Lyons, where they experienced a few minor miscues.

“It’s actually tricky with not being on the road as much to stay rehearsed,” Mehta admitted during our interview earlier that month before the Jennys landed among my top five acts of the festival, joining Rhiannon Giddens, the Revivalists, Lake Street Dive and the Dave Rawlings Machine (with Gillian Welch). “Everybody has time to do what they want creatively outside of the band and has time to be with their families so that when we get together, we haven’t overworked the music.It’s easier to kind of enjoy that part of life when you’ve got a full life elsewhere. And I think that we have such incredible audiences. … It’s hard not to really feed off that. And I think that when you’re constantly touring, it doesn’t have the impact it does because you’re seeing it all the time. … [With fewer dates], we’re enjoying the music because we’re not overdoing it, so it’s a good recipe for being out there and really being happy that we’re out there.” 

Heather Masse
Heather Masse is the youngest member of the Wailin’ Jennys.

Yet mistakes do happen, adding to the charm and spontaneity that goes with performers proving they’re still human while striving for perfection. The Jennys’ rocky start to Lyons show opener “Bright Morning Stars” might have been due to Mehta spraying hand soap on her shirt just before they hit the stage at 3:15 p.m. The rest of their 75-minute set was flawless, with accompaniment by Richard Moody and Dobres. And while faster-paced numbers like “Come All You Sailors”, “Racing With the Sun”, and “Deeper Well” might sometimes be missing in a live setting, the comfort, and joy of a softer, soul-soothing approach help make up for their absence. 

Preceding “One Voice”, probably the Jennys’ most-performed concert number, Moody offered a warm message to the crowd that echoes some of her lyrics from the group’s formative years. 

“This is a song that I wrote at a festival, not unlike this one, where I was very inspired by the idea of people coming together and celebrating life and celebrating each other through music,” she stated. “… It’s about singing together but it’s also, in a larger sense, about all of us coming together in the spirit of peace and harmony and hope.” 

This is the sound of voices three / Singing together in harmony / 
Surrendering to the mystery / This is the sound of voices three

Lyrics to the Wailin’ Jennys’ “One Voice”
Richard Moody
Richard Moody, Ruth’s brother, is an instrumental part of the Wailin’ Jennys’ touring band.

Back in Boulder

Flash forward five years (why would anyone want to remember so many months destroyed by the global pandemic anyway?) to find the traveling trinity back in Colorado again. However, it wasn’t a great start to 2022 for the Jennys, who postponed five early February shows “in the interest of safety,” but rescheduled them for 2023. They did manage to return to action on both U.S. coasts in March before the Rocky Mountains beckoned them.  

Though I missed their latest visit to Lyons for the Folks Fest on 14 August, six other towns in the state were blessed by their presence when summer began heading toward fall. Thankfully, their first-time performance at a sold-out, barn-like structure built in 1898, and seemingly suited for listening to roots music, meant another visit to Boulder, with guitarist Anthony da Costa adding electrical heft to a mostly acoustical act that again included Richard Moody. Six of their best songs (and a traditional encore) performed at the Rialto more than 11 years ago, fortunately, found their way onto this 30 September set list. Plus, the 1,350-capacity Chautauqua Auditorium (in close proximity to the Flatirons hiking trails) was a significant upgrade compared to that adorable but compact 450-seat Loveland venue. 

“Boulder! How are you guys? (applause) What an amazing venue this is,” exclaimed Mehta, the night’s busiest Jenny, after they opened with “Swing Low Sail High” and “By Way of Sorrow,” the Julie Miller cover they released on a 2011 iTunes Session EP. “Unbelievable. … Colorado is one of our favorite states. (applause) Absolutely! … It’s nice for Ruth and I not to be on a flat surface for a little while. We come from the prairies of Canada. … It is so flat there that you can watch your dog run away for three days.” 

Comedy bits like that were entertaining enough for most of the spectators already familiar with their material (surprising the trio with a loud vote of confidence to confirm their attendance at previous Jennys concerts). Judging by the show of support throughout the rest of the evening, expect the Colorado crush hours to continue, hopefully for many more anniversary celebrations. 

Anthony da Costa
Guitarist Anthony da Costa has electrified Wailin’ Jennys’ audiences since joining the touring band in 2021.

Genuine Jennys’ Lovefest

Here’s a sample of some of the Best of Boulder 2022 from the Wailin’ Jennys during a show that included 18 songs over two sets (followed by two encores), several more punch lines, one 30-minute intermission, a fundraising drawing, and an earnest display of social awareness. 

Ride ’em, cowboy: Before delivering her spirited lead vocal on “When I Was a Cowboy”, Masse, unexpectedly the night’s funniest Jenny, explained that the family’s move to Taos was a result of realizing that living in Southern California “just really is not our vibe.” She then confessed, “I’ve always had a thing for cowboys. … I’m married happily, mostly you know, but (big laughs) my husband is not a cowboy. But since we’ve moved to Taos, there’s this glimmer of hope. (laughs) I’ve not quite hit ‘Buy’ but I’ve had a pair of chaps in my Amazon [shopping] cart for quite a while. (more laughs) Life is about to get a lot better, I think.” 

Speaking out: As part of the band’s work with the National Alliance on Mental Illness and New York Times bestselling author (The Explosive Child) and child psychologist Dr. Ross Greene, Mehta asked concertgoers to participate in a drawing to support that cause. “What this organization does, his works, what he writes a lot about is the idea that there’s no such thing as a bad kid,” she said. (The drawing’s winner, announced during the second set, received Jennys’ signed merchandise and an autographed copy of Greene’s book.) Published in 2018, Mehta’s own illustrated book Away But Never Gone, its title taken from her Bright Morning Stars song she’s described as a lullaby, covered similar ground, while serving as “a grief aid” for young children. The dedicated activist also brought attention to National Day for Truth and Reconciliation that’s recognized on 30 September every year in Canada. Calling out the mistreatment “of our indigenous people” in her country, and “that we must stop it,” she performed her song “Starlight” (from 2006’s Firecracker), addressing the victims of horrible atrocities that have taken place in Canadian provinces such as Saskatchewan. 

The Wailin' Jennys
The Wailin’ Jennys perform for the first time at the Rocky Mountain Folks Festival in Lyons, Colorado, in 2017.

Cover stories: Splendid a cappella renditions of songs written by Dolly Parton (“Light of a Clear Blue Morning”) and Paul Simon (“Loves Me Like a Rock”, including finger snaps and rhythmic claps) were popular choices. Yet Petty’s “Wildflowers” proved to be the Fifteen selection that drew the loudest cheers. That was even after the mention of another Petty number turned high expectations into temporary disappointment (and a collective “awwwww”) when Masse gently told the crowd, “We’re not gonna do that song.” Resurrecting her intro to a 2017 Folks Festival audience, Masse did draw hearty laughs when she disclosed that “Mary Jane’s Last Dance” was her favorite in middle school until she finally realized as an adult “that Mary Jane really was not who I thought she was. It just had this whole new meaning.” 

New-worthy: Masse’s “Ida’s Song” and Mehta’s “I Tried” were new tunes, giving Jennys fans hope that another new album might be on the way in 2023. A poignant song (with sweet harmonies) she wrote after the “beautiful home birth” of her daughter Ida on 14 January 2019, Masse confessed she was brought back to reality, adding to a crowd laughing after every line, “I was just so excited to meet this little person when I pulled her out of the water. And she just started SCREAMING REALLY LOUD! And she just continued to scream for the next four months. So it was a bit challenging. But it was a magical, peaceful time — when she was asleep.” 

Despite its ironic title, Mehta, who likes to kid about her own kids, takes her latest song seriously, harkening to when she worked with at-risk youth. A supervisor’s statement specifically about troubled youngsters that also pertained to people in general — “Everybody is doing the best they can with what they have and where they are” — was always worth contemplating. And over time she changed her initial opinion — “I’m like, ‘Nope! Absolutely not!’ — saying, “But as I get older, I think it’s true.” Handling lead vocals and drums simultaneously on “I Tried”, Mehta earned the crowd’s huge round of applause. There also was praise from Masse, who said, “I don’t know how she does it. She can play those things and sing at the same time.” Mehta drolly responded, “After you’ve had twin boys, you can pretty much do anything.”

More baby banter: After Masse’s birth anecdote near the end of the first set, Moody, the gentlest Jenny, shared her not-so-pleasant experience, saying, “I had a baby a few years ago now. And let me tell ya, it was not a water home birth. (big laughs) Nope. Let’s just leave it at that. It turned out OK but anyone who was not feeling it when Heather was telling that story, I gotcha.” Adding that five-year-old Woodson is playing piano and guitar, and making up songs on his own, Moody revealed she and her son now argue over who wrote her newest number, the free-and-breezy “Easy Way”, which hit all the high notes, including her lead vocals and banjo playing, in the second set. “Essentially, it’s about motherhood, parenthood, so he kind of did help me write it,” she conceded.

The Wailin' Jennys
Nicky Mehta, Ruth Moody and Heather Masse share a laugh during their Boulder Theater debut performance in 2015.

 Departing shots: Facing what they called a “hard curfew” at Chautauqua (nearing 10:00 on a Friday night, no less), the Jennys quickly returned for a double encore shot, beginning with a pretty version of Neil Young’s “Old Man” (age-appropriate for most of this audience, myself included) that included da Costa’s powerfully electric guitar solo, an element they could have used on the tranquil 40 Days track. Ending with their customary closer “The Parting Glass”, a tender and traditional Irish tune also on 40 Days, Moody prepared the audience by saying,If they turn off the power, it will be OK because we’re coming up there.” 

The Jennys have been known to transform into giggling schoolgirls at previous shows for this solemn swan song, like their first Boulder stop in 2015 which led to some false starts and apologies, and a consideration to scrap it completely until determination won out. Back then, I wrote, “That element of surprise and display of perseverance not only brought down the house but made its impressed inhabitants fall even more head over heels” for Mehta, Moody, and Masse. 

This time around, though, there were no cackles or chuckles, only slight smiles, as the Jennys walked to the foot of the stage, past the microphones and instruments, and confidently gathered themselves with hands at their sides. Their trance-like gazes and a cappella singing hypnotized the crowd for two minutes of heavenly bliss. Professionalism, maturity (and probably realizing there was an early wake-up call ahead of a long drive to Steamboat Springs the next day) prevailed in front of a full house. That just goes to show that after all these years, three’s a charm for a trio possessing 20/20 vision while still living in the moment. 

The Wailin’ Jennys’ Set List 

30 September 2022, Chautauqua Auditorium, Boulder, Colorado

Song (released album)
1. “Swing Low Sail High” (2011’s Bright Morning Stars)
2. “By Way of Sorrow” (Julie Miller cover on 2011 iTunes Session EP)
3. “Arlington” (2004’s 40 Days)
4. “Loves Me Like a Rock” (2017’s Fifteen)
5. “When I Was a Cowboy”
6. “Beautiful Dawn” (2004’s 40 Days)
7. “Ida’s Song” 
8. “Glory Bound” (2006’s Firecracker)

INTERMISSION (30 minutes)
9. “Light of a Clear Blue Morning” (Dolly Parton cover on 2017’s Fifteen)
10. “Bird Song” (2011’s Bright Morning Stars)
11. “Starlight” (2006’s Firecracker)
12. “Easy Way” 
13. “I Tried” 
14. “Cherry Blossom Love” (2011’s Bright Morning Stars)
15. “Wildflowers” (Tom Petty cover on 2017’s Fifteen)
16. “One Voice” (2004’s 40 Days)

“Old Man” (Neil Young cover on 2004’s 40 Days)
“The Parting Glass” (Traditional Irish tune on 2004’s 40 Days)

Heather Masse, Ruth Moody
Heather Masse and Ruth Moody greet fans at the Rialto Theater merch table during one of their first Colorado shows in 2011.