Singing and Songwriting, with The Wailin' Jennys

Key takeaways

The evolution of the band’s live performance approach reflects growing comfort and a desire to offer meaningful connection, especially during challenging times.
Vocal harmony and collaborative songwriting are central to The Wailin' Jennys’ identity, influenced by traditional folk, jazz improvisation, and iconic groups like the Indigo Girls.
Creativity often stems from spontaneous inspiration, routine, and deliberate practice, challenging the myth of divine inspiration and emphasizing active engagement with music.
Small lyrical and musical choices—like word order or phrasing—can significantly alter a song’s emotional effect, highlighting the importance of ownership and authenticity in songwriting.
Listening deeply and diversely influences creative work, illustrating that exposure to varied music broadens artistic horizons.

Summary

Introduction and Band Background

The episode begins with the host expressing excitement about the interview with The Wailin' Jennys, a talented folk group with over two decades of history. The band members—Ruth Moody, Heather Masse, and Nikki Mehta—discuss their formation, the origin of their name, and their rise to prominence through radio and live performances. The host shares his long-standing familiarity with Ruth Moody and expresses admiration for their vocal harmony and musical journey.

Creative Process and Live Performance Dynamics

The band members talk about their preparation for upcoming shows, including setlist decisions and how their approach to live performances has evolved over the years. They reflect on being more relaxed and less focused on perfection compared to earlier days, influenced by the global situation and their desire to offer comfort through their music. The conversation highlights the importance of song choices and listening to audience needs in their setlist planning.

Vocal Arrangements and Songwriting Approaches

The discussion explores vocal harmonies, with Heather Massey sharing her experience integrating into the band and their processes for rearranging vocal parts. They discuss experimenting with song structures—such as sharing leads—and writing songs with multiple narrators or characters, considering traditional story-songs and the influence of songwriting on storytelling. The band members also reflect on their evolving approaches over time, including improvisational techniques stemming from jazz backgrounds.

Influence of Music and Song Crafting Techniques

A detailed exploration of influential artists like the Indigo Girls and their impact on the band’s harmony and songwriting. They analyze specific songs, emphasizing lyrical and musical choices like phrasing, melody, and harmony. The conversation extends to songwriting inspiration, including spontaneous ideas, the importance of routine, and philosophical views on creativity—such as the concept of inspiration as a shared universal resource.

The Creative Spark and Songwriting Challenges

The host and guests delve into the moment when ideas turn into finished songs, describing it as a critical and almost magical process. They talk about how external influences, like travel or emotional states, can trigger inspiration, and how routines can sometimes block that spark. They also discuss the importance of trusting oneself, the influence of external tools like listening to good music, and the myth versus reality of divine inspiration versus deliberate craft.

Crafting Lyrics and Musical Nuance

The group examines the significance of subtle lyrical and musical decisions, like word order and phrasing, emphasizing how small changes can profoundly affect the song’s emotional impact. They touch on the importance of owning one’s choices as a songwriter and the challenge of balancing artistic authenticity with technical considerations, including how improvisation and confidence shape final performances.

Wrapping Up with Music Recommendations and Final Thoughts

To conclude, each band member shares a favorite recent music discovery or personal playlist, highlighting the influence of listening habits on songwriting and musical growth. The episode ends with gratitude expressed for the interview, encouragement to support the show via Patreon, and a tease of upcoming episodes.

Show notes

The Wailin' Jennys have been singing together for more than two decades - recording albums, touring the world, and filling venues large and small. After all these years, the trio—Ruth Moody, Heather Masse, and Nicky Mehta—have reached both a plateau and an inflection point. What's it like for a musical group that's been together for that long; for singers who've found such perfect vocal harmony for one another? How do they each think of songwriting, and of creative work in general? On their recent west coast tour, they stopped by the studio for a chat about those things and more.

THE WAILIN' JENNYS ARE:

Ruth Moody - Banjo, Guitar, Vocals
Nicky Mehta - Guitar, Drums, Vocals
Heather Masse - Bass, Vocals

Featuring excerpts from the Jennys' albums Bright Morning Stars, iTunes Session - EP, 40 Days, and Firecracker

FEATURED/DISCUSSED:

"Total Eclipse of the Heart" by Jim Steinman, sung by Bonnie Tyler and Rory Dodd
"Paradise by the Dashboard Light," "I'd Do Anything For Love (But I Won't Do That)," "Objects in the Rearview Mirror May Appear Closer Than They Are" - by Jim Steinman sung by Meat Loaf
"Closer To Fine" and "Love's Recovery" by Indigo Girls from Indigo Girls, 1989
Big Magic: Creative Living Beyond Fear by Elizabeth Gilbert, 2016
Kirk's essay on creativity, "Follow The Spark"
Jeff Tweedy talking songwriting on The Ezra Klein Show
"What Am I Here For" by Jade Bird

MUSIC PICKS:
Heather: Bonny Light Horseman, Keep Me On Your Mind/Set You Free, 2024
Ruth: Aaron Neville, "Louisiana 1927"
Nicky: Afghan Whigs, Black Love

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AUGUST 2025 WHOLE-NOTE PATRONS

Melissa Lucas – Thomas McIlheran – Andy – Lisa Crotty – Rick Keeler – Elizabeth Culver – Meryl Allison – Robyn Metcalfe – Cesar – Corpus Frisky – Ben Barron – Catherine Warner – Damon White – Jay Swartz – Rush – Daniel Hannon-Barry – Christopher Miller – Jamie White – Christopher McConnell – David Mascetti – Joe Laska – Ken Hirsh – Melanie Andrich – Jenness Gardner – Nathaniel Bauernfeind – Paul Delaney – Sami Samhuri – Jeremy Dawson – AccessViolation – Dave Florey

AUGUST 2025 HALF-NOTE PATRONS

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