The legendary Loudon Wainwright III, whose career has spanned over five decades, is known for his deeply personal songwriting and sharp wit – and oversharing. The patriarch of the Wainwright folk dynasty (which includes Rufus, Martha, their late mother Kate McGarrigle, as well as Lucy and her mother Suzzy Roche), Loudon reflects on the balance between oversharing and maintaining privacy in his music in this episode of Basic Folk. He candidly discusses the lines he draws when writing about family and how his experiences with grief have shaped his art. I'm proud to say that I think we found a line he would not cross in our conversation! Listen in to hear history in the making.

We also discuss his latest live album, 'Loudon Live in London,' and his unique ability to unsettle and surprise his listeners during performances. We talk about his late father and namesake, Loudon Wainwright Jr., the famous writer for LIFE Magazine, who is present in everything LW3 does. We dive into his early days, including insights on his debut album thanks to a recent essay by Morrissey that highlights its significance. Moz points out that Wainwright has "the pep and readiness of someone who knows we will all soon be skeletons." After reading Loudon's very detailed memoir, Liner Notes, I had to ask him about his relationship to memory and also his reputation for memory. Loudon also touches on his acting career, revealing how roles in popular films – especially Big Fish and Knocked Up – have introduced him to new audiences. Elsewhere he reveals that he was at the 1965 Newport Folk Festival where Dylan went electric and shares his memories of that fateful day.

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Olivia Ellen Lloyd's latest album, 'Do It Myself,' sees the West Virginia-born Brooklyn-based songwriter reflecting on the powerful imagery of water. She shares how it has been a source of grounding and calmness in her life, from childhood memories spent on the Potomac River to her current love for the ocean, these elements have shaped her artistic journey. In an interesting twist, it was her friends and family that pointed out that she's always trying to get around water. From there, she reflected on the positive impact that being in and around water has had on her mental state.

Olivia also opens up in our Basic Folk conversation about her complex relationship with her hometown of Shepherdstown, West Virginia, where she's experienced both hardships and good memories (her grandfather was actually the mayor and there's a street named after him). Ultimately she decided to leave, but she still spends about half the year there. She talks about how, especially on the new album, her sound is impacted by the duality of small-town life versus her evolving relationship with New York City. We also discuss the foundation of her musicality, which was strongly influenced by her late father, who stressed the importance of learning music by ear. As she navigates her identity as an independent woman in the music industry, she discusses the challenges of societal expectations and the importance of self-reliance. With humor and vulnerability, Olivia Ellen Lloyd explores themes of resilience, love, and the struggles many women face in finding their voice and place in the world.

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Will Oldham, also known as Bonnie "Prince" Billy, has led an illustrious, sometimes mysterious career which has spanned decades and genres. Hailing from and still living in Lexington, KY, in our Basic Folk conversation Will reflects on his journey from a young artist struggling to find his place in the music world to a seasoned musician who embraces collaboration and creativity.

We dive into his latest album, 'The Purple Bird,' discussing the pivotal role of producer David Ferguson in Will's artistic evolution. He reveals how working with Ferguson and a host of talented Nashville musicians transformed his songwriting process and solidified his sense of belonging in the music community. With a mix of humor and heartfelt honesty, Will describes the joy of collaboration and the unique energy that comes from working with seasoned artists, particularly those from older generations.

Throughout this episode of Basic Folk, Will also touches on the contrasting emotions evoked by his songs, especially when dealing with serious themes wrapped in upbeat melodies. He draws parallels to the works of Phil Ochs, highlighting the importance of addressing difficult subjects through art. As we wrap up, he shares personal anecdotes about his family and the influence of his daughter on his music. Thanks to Will for making a wonderful record and being so willing to get seriously deep into some of its themes!

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Rose Cousins and Edie Carey's friendship has blossomed for over two decades. On the occasion of Rose releasing her new album, 'Conditions of Love - Vol 1,' the pair appear on Basic Folk to discuss the new music. They reflect on their early days and their first meeting as well as the ways they’ve influenced each other's careers and personal growth.

To witness Rose's new album through the eyes (and ears) of her best friend feels like a huge privilege, a front row seat looking into what the human heart and mind are capable of. Edie prompts Rose to expand on the challenges of balancing love and freedom, the complexities of navigating midlife, and why the piano is her soulmate. With humor and depth, they tackle the big questions of life, love, and the creative process, revealing the layers of their artistic identities.

"I just had a really moving, hilarious, enlightening conversation with my best friend Rose Cousins," Edie reflects. "We talked about vulnerability, middle aged gardening, accidentally putting in one another’s eye contacts, and befriending our own mortality. We also talked about her stunning new record, 'Conditions of Love - Vol 1.'"

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When mandolinist Sierra Hull was little, her dad told her she was really good "for a ten year old." The older Hull knew Sierra had a fiery passion for the instrument and he knew exactly how to motivate his daughter. He went on to say that if she wanted to go to jams and porch-play for the rest of her life, she'd learned enough. He gave her realistic advice that, if she wanted to dedicate her life to music, she would have to work really hard. Because "that 10 year old cute thing is gonna wear off." Sierra, who would draw pictures of herself playing at the Grand Ole Opry with Alison Krauss and doodle album covers with the Rounder Records logo, took his advice to heart and got to work.

Since then, Hull has shared the stage with more heroes than one could count, she's inspired a new generation of younger players, she's released five albums, and is considered a master of the mandolin. Originally from the small town of Byrdstown, Tennessee, her new album, 'A Tip Toe High Wire,' is set for release March 7. In our Basic Folk conversation Sierra reflects on how growing up in a small town shaped her musical identity alongside bluegrass, gospel, and family traditions. She shares memories of family gatherings filled with music featuring Aunt Betty and Uncle Junior, the profound influence of church hymns, and how these experiences continue to resonate in her playing and songwriting.

Sierra also discusses the significance of 'A Tip Toe High Wire,' her first independent release, highlighting the freedom and growth that come with that independence. She emphasizes the importance of authenticity in her music, allowing herself to explore new sounds while remaining grounded in her bluegrass roots. Elsewhere in the episode, she opens up about her personal growth, the pressures of being labeled a child prodigy, and her journey toward embracing imperfection in her art. We also dive into what we'll call her "Stevie Nicks Era" with the amazing cover-art on the new record. Sierra enjoys playing with elaborate styles in her album artwork and red carpet looks (helloooo CMA Awards). With a candid perspective on the challenges of the music industry, she encourages listeners to find joy in the process while appreciating the beauty of vulnerability

Also woo hoo!!! Happy Basic Folk 300!!!!

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Editor’s note: Basic Folk is pleased to introduce our listeners to one of our favorite podcasts by sharing an episode in our feed!

Folk Files is a podcast hosted by Olivia Harding that seeks to uncover the mysteries of folk music through the ages and dive deep into the tangled history of murder ballads, sea shanties, rebel songs, and other music that has withstood the test of time.

 “Shady Grove” is an Appalachian folk song that is often linked to the English ballad “Matty Groves”. But what is the actual relationship between them? This episode of Folk Files discusses the meaning of “Shady Grove” and untangles the origins of these two songs.

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You probably know Gary Louris as the leader of The Jayhawks – or as they refer to themselves, “a band from Minnesota.” The Jayhawks are pioneers of roots rock, alt-country, and Americana. Whatever you wanna call it, they’ve been making records where rock, pop, country, and other forms of American roots music overlap since the mid-1980s.

But Louris’s hidden superpower is that he’s kind of like a musical Swiss Army knife – he’s basically got a creative skill for any application. Want him and his band to serve as accompanists for some of the most distinctive singer-songwriters, like Wesley Stage and Joe Henry? He can do that. Looking for achingly-perfect, near-fraternal harmonies on hit songs like Counting Crows’ “Mr. Jones”? He can (and did) do that. If you’re the Tedeschi Trucks Band or The Chicks and you’re looking for someone to write you some catchy, melodic, roots-pop songs? Gary’s your guy. If that’s not enough, he has also produced records for artists like Dar Williams, The Sadies, and The Jayhawks, too. Whatever your musical need may be, chances are that Gary Louris can do it.

In between all these varied musical roles, Louris has also found time to release several solo albums, the newest of which – 'Dark Country' – was released earlier this month. He recorded it mostly solo in his home studio and the word on the street is that this collection of songs, inspired by his wife, is his most intimate and romantic album yet. I’ve been a big fan of Gary Louris for basically my entire adult life and enjoyed our wide-ranging Basic Folk conversation, touching on the way technical limitations can shape an artist’s style, what he’s learned from a career’s-worth of collaborations, his process working on his new solo album, the relationship between versatility and longevity, and what the influence of romance on his songwriting looks like now, in the fifth decade of his music career.

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Singer-songwriter Lilly Hiatt has an interesting way of working melodies and a down to earth way of telling stories about her life and about how she sees the world. All of her albums have cool, crunchy guitar parts that take folk songwriting to a new rockin' level. On her new album 'Forever,' Hiatt's diverse influences are woven into songs that touch on everything from relationships to anxiety and mental health to good old-fashioned rock & roll.

In our Basic Folk conversation, we talked about the lessons that Lilly learned growing up the daughter of legendary songwriter John Hiatt and what it meant to her to see her dad go through the ups and downs of the music business while having the humility and self belief to keep going. She also talks about how she thinks about herself as a performer – and how that's changed since the pandemic. Before the pandemic Hiatt had a couple of really big records ('Trinity Lane,' 2017 and 'Walking Proof,' 2020) that gained a lot of hype and attention. Once coronavirus hit, she had to sit in the house and ask the big questions like a lot of us did. She sat with the loneliness, alienation, and uncertainty.

You can hear in our interview just how much mutual respect and admiration we have for each other and how much belief we have in one another, not only as songwriters, but as women and as people who are in recovery. Very LYLAS vibes, lots of laughs.

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SiriusXM's folk radio programmer Mary Sue Twohy has not had a straight career path, but it's certainly been adventurous. Mary Sue, who is about to be inducted into the Folk DJ Hall of Fame, has held many different jobs over her life, most notably as a touring singer songwriter and as a beloved folk radio programmer, host and active community member. It all began in a vibrant musical and creative home in Aberdeen, New Jersey. With fond memories of family gatherings filled with guitars (and banjos!), laughter, and a distinctive 70s aesthetic, Mary Sue reflects on how her father's love for folk music has shaped her own artistic journey. We dive into how his favorite music, from Joan Baez to the Nitty Gritty Dirt Band, have resonated throughout her life.

As a seasoned musician and now a prominent figure in the radio world, Mary Sue discusses her transition from performing artist to radio programmer at SiriusXM (she currently manages The Village, the folk channel along with several other channels). She emphasizes the importance of connection in radio, both with the audience and the artists she showcases, highlighting how her background as a musician allows her to curate a unique listening experience. Her passion for folk music and her commitment to uplifting diverse voices within the genre shine through as she shares insights on compassion, community, and the healing power of music.

Throughout our conversation, Mary Sue's authenticity and warmth are evident as she navigates topics like her hobbies outside of music, the significance of compassion in her work, and her recent induction into the Folk DJ Hall of Fame. We also touch on her thoughts about the Bob Dylan movie and engage in a fun lightning round where she shares her favorite songs and memorable moments from her career.

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Although the ever-enigmatic Sam Moss is not a great swimmer, he named his latest album 'Swimming.' The folk singer with a gentle demeanor is back with thoughtful songs and captivating melodies. Hailing from New England, Sam has carved out a unique niche in the folk world, blending naturalistic themes with an introspective approach to songwriting. We explore how his New England roots continue to influence his music – despite his current residence being Virginia – and how his upbringing in a family of visual artists has shaped his artistic sensibilities.

Sam also talks about how movement and the natural world inspire his songwriting, if not with more oblique lyrics. We dig into his latest album 'Swimming,' where he boldly embraces more direct lyrical expressions; we discuss the balance between mood and narrative in his work, too. Our Basic Folk conversation touches on his journey from a shy young musician to a confident performer, as well, thanks in part to the encouragement of close friends like Jackson Emmer. He counts Emmer, who he played with in old-time duo The Howling Kettles, as one of his greatest inspirations for following his own creative arrow in music.

Elsewhere in the episode, we explore Sam's passion for woodworking, a skill he honed as a respite from musical burnout. He describes the satisfaction of crafting tangible objects and how this practice complements his musical endeavors. We also really dive into his feelings around the word "gentle," which is often used to describe his music and persona. He doesn't actually mind being known as a gentle person– in fact, he hopes people do find his music soft and tender and, in that gentleness, that they still leave feeling his songs' striking impact.

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