In 2022, at 75 years-old, Loudon Wainwright III released Lifetime Achievement—an aptly titled album from a songwriter whose debut came more than fifty years earlier.

Over the decades, Loudon has built a reputation for his confessional style, writing candidly about the struggles and absurdities of family life, failed relationships, and the scars of parental abandonment. While his subject matter can be heavy, he often balances it with wit and humor. You’ll hear that today when he performs “Fam Vac” and “Back in Your Town” from Lifetime Achievement.

In this conversation with Bruce Headlam, Loudon reflects on how he leaned into his upper-class upbringing when he first began performing professionally, what it was like collaborating with guitar virtuoso Richard Thompson in the 1980s, and the magical feeling of stepping on stage for the very first time.

You can hear a playlist of some of our favorite Loudon Wainwright III songs HERE.

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Great musical chemistry often starts at home. Think of family bands like Sly and the Family Stone, The Beach Boys, the Bee Gees, Haim, Oasis, AC/DC, and The Jacksons. Infinity Song, our guests today, carry on that tradition. Siblings Momo, Abraham, Angel, and Israel Boyd grew up between Detroit and New York City, sharpening their sound wherever they could: in church, in the park, on subway platforms, even around the kitchen table.

Their devotion to performing eventually carried them to bigger stages, guided by their father and manager John Boyd and supported by Jay-Z’s Roc Nation. Along the way, they’ve developed a unique blend of R&B and folk that they describe as modern-day soft rock.

For today's episode, Justin Richmond sat down with the Boyd siblings live at the Tribeca Festival in New York. They talked about the role music has always played in their family, the pivotal moment when their dad saved the day in a high-stakes meeting with Jay-Z, and they performed a couple of tracks from their album Metamorphosis Complete.

You can hear a playlist of some of our favorite tracks from Infinity Song HERE.

And you can hear our Fall playlist HERE.

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Margo Price’s new album, Hard Headed Woman, was recorded in the heart of Nashville at the legendary RCA Studio A—the very place where the “Nashville Sound” was born, and where greats like Merle Haggard, Dolly Parton, and Charley Pride have all recorded. It’s the perfect setting for Margo, who’s as much a student of country’s rich history as she is a fan of its fearless rule breakers. She’s never taken the straight path herself, a journey she tells in her 2022 memoir, Maybe We’ll Make It.

On today’s episode, Bruce Headlam talks with Margo Price about the making of her new album and her creative partnership with her husband and longtime collaborator, Jeremy Ivey. Margo also shares her thoughts on the inauthenticity of mainstream country, and why she continues to stay committed to pouring both extreme craft and care into every song she writes.

You can hear a playlist of some of our favorite Margo Price songs HERE.

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Soaring, lush and steeped in soul, Annahstasia has a voice that feels distant and intimate all at once. She was scouted in high school for a career in pop music but after some strange dealings set out down the road of self discovery.

You can hear what she uncovered about herself and her artistry on her serene new album, Tether. The album was recorded live in studio and is stripped to the bone allowing her voice and poetry to shine through unencumbered by any hint of pop production.

Justin Richmond spoke to Annahstasia about her journey through music, which includes earning a four-year degree, opening for the great Lenny Kravitz, and co-starring in Kendrick Lamar’s “Luther” music video.

You can hear a playlist of some of our favorite Annahstasia songs HERE.

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Chrystia Cabral is the experimental, often mystically-inclined Oakland artist who records as Spellling. Since her 2019 debut, she’s built a reputation for richly imaginative music that defies easy categorization. Her third album, The Turning Wheel, earned a rare perfect 10 from notoriously discerning online critic Anthony Fantano, who called it “stunning and beautiful.”

Today, Spellling joins Justin Richmond to talk about the making of her latest release, Portrait of My Heart—a bold evolution that deepens her blend of avant-garde, pop, and rock by adding new layers of mysticism and theatricality. She also reflects on her transition from teaching to touring, the intention behind every element of her sound, and the early days of her music-making, when she first began experimenting with gear.

You can hear a playlist of some of our favorite Spellling songs HERE.

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Daron Malakian first made his name as the enigmatic guitarist and songwriter behind System of a Down. Between 1998 and 2005, the band released five albums—three of which debuted at number one on the Billboard charts. In 2006, System announced an indefinite hiatus.

Eager to keep creating, Daron launched a new project: Scars on Broadway. Their debut album arrived in 2008 to critical acclaim.

Since then, he’s reunited with System for a series of live performances—including a recent South American tour that drew massive crowds. Their final stop in São Paulo, Brazil, attracted an estimated 75,000 fans.

Now, after seven years in the making, Daron is releasing Addicted to the Violence, the third Scars on Broadway album—featuring what he considers some of the best songs he’s ever written.

On today’s episode, Leah Rose sits down with Daron to talk about why he believes he was destined to be a rock star, and how his parents’ journey from Baghdad to Hollywood helped make that dream possible. He also explains what people often misunderstand about his relationship with System frontman Serj Tankian—and reveals the surprising contrast between his outrageous onstage persona and who he really is offstage.

You can hear a playlist of some of our favorite Daron Malakian songs HERE.

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Here’s a preview from a new podcast, Charlie’s Place. How did a Black man in 1940s Jim Crow South open a club where Black and white people danced together? Charlie’s Place was revolutionary, and that meant it was dangerous. Host Rhym Guissé explores the unbelievable true story of Charlie Fitzgerald, a mysterious Black businessman whose nightclub became an unlikely site of integration in 1940s Myrtle Beach. Charlie broke down racial barriers through the power of music and dance, hosting some of the greatest musicians of our time: Little Richard, Count Basie, Ray Charles, Duke Ellington, and many more. But who was Charlie? How did he rise to power? And what price did he pay for achieving the impossible—an integrated club in the Jim Crow South? This is a story of joy and passion that erupted into violence and changed a community forever.

Listen to Charlie’s Place wherever you get your podcasts. Binge the entire season early and ad-free by subscribing to Pushkin+. Sign up on the Charlie's Place show page on Apple Podcasts or at pushkin.fm/plus.

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Today, we’re joined by one of the most inventive and electrifying vocalists in modern soul music: Bilal. 

Since the release of his debut album 1st Born Second in 2001, Bilal has defied categorization by design and by circumstance. With a voice that shifts effortlessly from a whisper to a wail, and from jazz to gospel to outer space, he’s carved a singular path through the world of music. Whether lending hooks to Kendrick Lamar or collaborating with Erykah Badu, Bilal has long been your favorite singer’s favorite singer.

Now, he’s back with a brilliant new project: Adjust Brightness. Bold, cinematic, and emotionally raw, it’s his most cohesive work since his debut—a swirling, psychedelic blend of soul, jazz, hip-hop, and feeling. And as if that weren’t enough, Bilal has also just released Live at Glasshaus, an intimate and explosive set that captures the unpredictable energy of his live shows.

Today, Bilal opens up to Justin Richmond about the making of Adjust Brightness, how he prepares for those electrifying live performances, and why chasing musical and spiritual freedom has always been his true north.

You can hear a playlist of some of our favorite Bilal songs HERE.

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Mike Shinoda took a bold step last fall when he reintroduced Linkin Park with a new lineup featuring drummer Colin Brittain and singer Emily Armstrong as lead vocalist—taking on the role once held by Chester Bennington, who died by suicide in 2017.

Mike, who co-founded Linkin Park in 1996, has long served as the group’s de facto producer, as well as its MC and keyboardist. The band rose to massive success in the 2000s, with a run of genre-blending albums that have collectively sold more than 100 million copies worldwide.

In November, Linkin Park released From Zero, their eighth studio album and the first with Emily Armstrong as frontwoman. The record has already surpassed three billion streams online.

On today’s episode, Leah Rose talks to Mike Shinoda about why he chose not to retire Linkin Park—and instead took the creative risk of reinventing the band nearly 30 years after its formation. Mike also shares his favorite Linkin Park songs of all time and explains how the band managed to stand apart from the bro-centric, frat-boy culture that defined much of early-2000s nu-metal.

You can hear a playlist of some of our favorite songs from Mike Shinoda and Linkin Park HERE.

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Jesse Malin quite literally came of age onstage in the gritty clubs of New York City. At just 12 years old, he fronted Heart Attack—one of the earliest hardcore punk bands. After the band broke up in ‘84, Jesse went on to play in other groups, including Hope, and later co-founded D Generation, a glam-punk band that toured extensively through the '90s, opening for acts like Kiss, the Ramones, and Social Distortion.

In the early 2000s, Jesse launched a solo career, trading hardcore for a more singer-songwriter-driven approach. As a solo artist, he’s collaborated with a wide range of musicians, including Bruce Springsteen, Lucinda Williams, and Billie Joe Armstrong. A true musician’s musician, Jesse has long been a beloved figure in the rock community.

So when he suffered a rare spinal stroke in 2023 that left him temporarily paralyzed from the waist down, that community rallied around him. The result was Silver Patron Saints: The Songs of Jesse Malin—a 2024 tribute album featuring covers of his songs by friends and admirers. Jesse is also debuting a musical this fall called, Jesse Malin’s Silver Manhattan: A Musical Guide To Survival, at the Gramercy Theatre in New York.

On today’s episode, Bruce Headlam talks with Jesse Malin about his colorful upbringing in Queens, how he found the nerve to try out for a gig at CBGB’s at age 12, and what it was like during the formative years of New York’s hardcore scene. Jesse also shares how his “positive mental attitude” helped him through the toughest chapter of his life—recovering from the stroke that nearly ended his ability to walk.

You can hear a playlist of some of our favorite Jesse Malin songs HERE.

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