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What happens when a pop song named after a movie star sends you down a rabbit hole about fame, creativity, culture, and who actually controls the art we consume? This week, Joe and Toby dive into Adela’s breakout hit “Nicole Kidman,” tracing the young Slovakian artist’s journey from being cut from Dream Academy to finding her own lane and landing on the charts. They unpack the song’s all-star writing team, Adela’s fascination with American pop culture, the inspiration behind the Nicole Kidman reference, and the intriguing tension between the polished pop machine and the much more vulnerable artist underneath it all. But, naturally, the riff doesn’t stop there. The conversation expands into the supersaturation of modern pop culture, the disappearance of musical tastemakers, Spotify’s genre bubbles, the value of being pushed outside your musical comfort zone, and why curiosity about unfamiliar music might teach us something about curiosity toward unfamiliar people and cultures, too. Along the way: Eyes Wide Shut, Tom Cruise fatigue, a Mount Rushmore of actresses, Lorna Shore, libraries, jelly beans, the return of the episode playlist, and an important question for every young artist navigating the industry: when you finally get the success you’ve been chasing, how much control do you have over what comes next? Joe and Toby also build a musical “flight” inspired by the episode, connecting Adela to the artists, writers, samples, influences, and wonderfully strange detours that make the Riffs on Riffs rabbit hole what it is. Give it a listen. Let it breathe. And maybe try something you normally wouldn’t. Learn more about your ad choices. Visit megaphone.fm/adchoices See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

What happens when the artist isn’t real, the voice never lived, and the face can change with a prompt? In a different kind of Riffs on Riffs episode, Joe and Toby dive headfirst into the increasingly strange world of AI-generated music, beginning with the controversy surrounding virtual artist Sienna Rose and accusations of “digital blackface.” From there, the conversation gets much bigger: Who owns the culture an AI artist borrows from? What does it mean to “do the work” when a machine can generate the finished product in seconds? And if audiences can no longer tell what’s real, does it matter? Joe and Toby wrestle with both sides of the technology. AI can democratize creativity, help someone hear an idea they otherwise couldn’t produce, and become a powerful tool for experimentation. But when the shortcut replaces the people, the collaboration, the mistakes, the arguments, the second takes and the happy accidents, something important disappears. Toby calls it the “angel’s share”: the unmeasurable piece of the creative process that evaporates when the humans are removed. The rough edges. The outtakes. The moment a band loses power and keeps playing anyway. The producer challenging the songwriter. The note that isn’t perfectly in tune but somehow feels exactly right. The conversation also takes on our growing obsession with perfection, algorithmic manipulation, AI bias, cultural appropriation, physical media, the resurgence of vinyl and CDs, and why holding a fifty-year-old record suddenly feels almost radical in a world of infinitely editable digital artifacts. At the center of it all is a deceptively simple question: are we using technology to enhance human creativity, or slowly engineering the humanity out of it? And maybe there’s a more hopeful possibility. Perhaps the rise of AI ultimately creates a human renaissance, one where we learn what machines are good at while rediscovering everything that makes real people, real performances, and real connection irreplaceable. Learn more about your ad choices. Visit megaphone.fm/adchoices See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

It’s baseball playoff season, so Joe and Toby are taking the mound for a different kind of pitch. In this special “Wild Pitches” episode, each host brings three artists they think deserve a bigger audience, whether they’re genuinely under the radar, underappreciated in the U.S., or simply making music too good not to share. Toby makes the case for Kareen Lomax and her adventurous, genre-bending sound; the organic R&B and vintage warmth of sunandmoon; and Malia, whose new project If I’m Being Honest pairs a rich, mature voice with deeply personal songwriting. Joe counters with South London sibling duo Wasia Project and the lush, cinematic Nocturne; longtime favorite LP, whose unmistakable voice and songwriting have built a massive following overseas; and UK rock band Nothing But Thieves, powered by huge songs and the remarkable vocals of Conor Mason. Along the way, the conversation wanders exactly where a Riffs conversation should: Missy Elliott, Stevie Wonder, George Michael, family collaborations, the return of organic musicianship, the virtues of a great EP, Critical Role, overly long fantasy novels, and what makes an artist truly “vinyl worthy.” Six artists. Two hosts. One highly questionable competition. Listen, make your own picks, and then tell us who won. Riffs On Riffs is brought to you by DistroKid, the ultimate partner for taking your music to the next level. Our listeners get 30% off your first YEAR with DistroKid by signing up at http://distrokid.com/vip/evg Learn more about your ad choices. Visit megaphone.fm/adchoices See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

This week on Riffs on Riffs, Joe and Toby hop aboard Stella Lefty’s “Boston,” a deceptively simple song about what happens when something good shows up and your first instinct is to run the other way. The conversation starts with the noise surrounding Lefty: accusations of nepotism, comparisons to Noah Kahan’s “Stick Season,” questions about borrowed melodies, and the eternal debate over whether any song can truly be original. From Bruno Mars and Stevie Wonder to Tom Petty, the Chili Peppers and J Dilla, Joe and Toby explore the blurry lines between influence, inspiration and imitation, and wonder whether sometimes we’d all be better off turning on airplane mode and simply listening to the music. They also dig into the unusual way “Boston” grew from a short social-media snippet into a finished song after listeners responded to it, sparking a larger conversation about the benefits and dangers of letting audiences shape creative work. But the heart of the episode is the song itself. A lyric about wanting to run when someone is actually treating you well opens the door to self-sabotage, vulnerability and what Toby calls being “scared of success.” From there, “Boston” becomes a launching point for a much bigger conversation about hope as a verb, resilience through struggle, sacrifice, and the things we learn simply by showing up when we’re nowhere near our best. Plus: terrible dates, pineapple on pizza, mysterious arm name tags, childhood book “borrowing,” TV shows that stayed too long at the party, and a surprisingly passionate defense of the word “courting.” Sometimes a song doesn’t have to reinvent music. Sometimes a good song is just a good song. Riffs On Riffs is brought to you by DistroKid, the ultimate partner for taking your music to the next level. Our listeners get 30% off your first YEAR with DistroKid by signing up at http://distrokid.com/vip/evg Learn more about your ad choices. Visit megaphone.fm/adchoices See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

What happens when R&B, grunge, hip-hop and a healthy disregard for genre boundaries all collide? This week, Joe and Toby dive into Steve Lacy’s “Oh Yeah?,” a track that found new life through the Spider-Man soundtrack and opens the door to a much bigger conversation about where music and culture itself is headed. They unpack Lacy’s stripped-down, almost stream-of-consciousness approach to songwriting, the vulerability running through his music, and why today’s artists seem increasingly comfortable trading polish and perfection for something more immediate and human. From the return of live bands to bedroom production, alternative R&B, retro soul and artists who refuse to stay neatly inside a single genre, the musical map is getting wonderfully messy. But the conversation goes beyond music. Joe and Toby wrestle with the weight younger generations are carrying, the tension between fatalism and hope, and whether the same generation questioning old rules about music is also preparing to rewrite some of the rules about work, culture and society. Plus, they make the case for building your own yearly soundtrack instead of letting Spotify do it for you, and share what they’re listening to now, including Baby Rose, Jungle, Buttered, Nothing But Thieves, LP, Lucky Daye, Leon Thomas and more. Riffs On Riffs is brought to you by DistroKid, the ultimate partner for taking your music to the next level. Our listeners get 30% off your first YEAR with DistroKid by signing up at http://distrokid.com/vip/evg Learn more about your ad choices. Visit megaphone.fm/adchoices See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Ariana Grande is going a little feral, but she’s doing it with remarkable restraint. This week, Joe and Toby dig into “Petal” and Ariana’s latest album, exploring how one of pop’s most gifted vocalists is choosing subtlety over fireworks and using her music to say some things she may have been too polite to say before. The image of a flower pushing through concrete becomes the perfect metaphor: resilience isn’t always about becoming harder. Sometimes it’s about staying soft, authentic, and unmistakably yourself despite everything pushing against you. From there, the riffs go where the riffs go. The guys wrestle with the price of fame, our strange sense of ownership over artists, the pressure to constantly achieve more, and why walking away can sometimes be as courageous as pushing forward. They get into work-life balance, artists like André 3000 and Fiona Apple who chose different paths, handwritten letters, looksmaxxing, aging, beauty standards, and the exhausting pursuit of external validation. Ultimately, it all comes back to boundaries: knowing what belongs to the world, what belongs to you, and when it’s time to put up the stop sign. Plus: Earl Grey, Doctor Doom, gym mirrors, gray beards, terrible tours, and a surprisingly useful theory involving speed bumps. How are you growing through the concrete? Learn more about your ad choices. Visit megaphone.fm/adchoices See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Prepare for an intergalactic funk transmission as Joe and Toby explore “Fabiano” by Quebec duo Angine de Poitrine. Armed with masks, polka dots, microtonal guitars, dizzying rhythms, and enough looping pedals to frighten a Guitar Hero champion, these two musicians create a sound that is equal parts math rock, funk, jazz, and delightful absurdity. But the riffs quickly launch a much bigger conversation. What does anonymity allow an artist to create? Can limitations actually make us more inventive? Who should be trusted with an unfinished idea, and how do we keep one careless opinion from crushing the creative cake before it has finished baking? Joe and Toby also dig into the power of long-term creative partnerships, the confidence born from struggle, the tension between artistic freedom and the desire for recognition, and the identities that remain underneath our everyday careers. Plus, they consider what their 13-year-old selves would think of them today and share some of the artists currently filling their headphones. Learn more about your ad choices. Visit megaphone.fm/adchoices See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

What are you willing to die on a hill for? For rising British singer-songwriter Sienna Spiro, the question becomes a haunting exploration of loyalty, stubbornness, and the moment you realize you may be fighting for someone who would never fight for you. In this episode, Joe and Toby dig into Spiro’s breathtaking single “Die on This Hill,” from its stripped-back piano opening and sweeping string arrangement to the audible sigh that closes the track. They explore how a failed attempt to learn “Bohemian Rhapsody” sparked the song, why it took countless versions to uncover its true form, and how Spiro learned that restraint can sometimes reveal more than vocal fireworks. The conversation also traces the influences behind her timeless sound, including Stevie Wonder, Billy Joel, Nina Simone, Adele, Lana Del Rey, and Amy Winehouse, along with the remarkable praise she has received from Sir Elton John. Along the way, Joe and Toby wrestle with artistic vulnerability, stage personas, the value of creative repetition, and why listeners may be craving unmistakably human music in the age of AI. Plus, the guys share what they have been listening to lately, champion artists still bubbling beneath the algorithm, and make the case for why Sienna Spiro is unquestionably vinyl worthy. Learn more about your ad choices. Visit megaphone.fm/adchoices See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Joe and Toby dive into Olivia Rodrigo’s “Drop Dead,” unpacking the emotional precision, lyrical sharpness, and intimate vocal delivery that make her music feel like an inner monologue. The conversation explores how Rodrigo’s songwriting connects across generations, pulling younger listeners into the immediacy of heartbreak while transporting older listeners back to their own formative relationships. The hosts also trace the song’s sonic and cultural echoes, from The Cure and ’80s/’90s alternative textures to the cinematic potential of Rodrigo’s catalog as the soundtrack for teen romance, obsession, horror, or beautifully awkward coming-of-age stories. Along the way, they discuss Amy Allen’s songwriting influence, Dan Nigro’s production, the strange experience of celebrity in the wild, and why great songs can bridge age, memory, and emotional time travel. As always, the episode wanders joyfully into side quests, including New York celebrity sightings, Helena Bonham Carter near-collisions, Dash & Lily, Spider-Verse, PM Dawn, and a recommendation for Australian artist Ethan French. It’s a conversation about Rodrigo’s artistry, but also about why certain songs don’t just get heard. They follow you around. Learn more about your ad choices. Visit megaphone.fm/adchoices See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

This week on Riffs on Riffs, we tackle one of the most polarizing artists of the modern era: Drake, his track “Janice STFU,” and the massive cultural machine surrounding the release of Iceman. Alonog the way, Toby and Joe discuss celebrity, marketing, authenticity, attention spans, social media, AI, and whether modern culture has become addicted to constant stimulation. We break down Drake’s ambitious album rollout, from elaborate promotional stunts and livestreams to the strategy of dominating conversation through sheer volume. Joe compares Drake to KISS as a case study in marketing genius. The result is a fascinating discussion about what makes an artist culturally unavoidable, even when critics and fans can’t agree on the music itself. The conversation also revisits the lingering shadow of Drake’s legendary feud with Kendrick Lamar. Was it genuine animosity, performance art, or some combination of both? And what does it say about modern audiences that conflict itself has become part of the product? From meditation and dopamine addiction to birds nesting outside Joe’s front door, the episode becomes a reflection on what many of us seem to be craving right now: something real. We explore how technology, algorithms, and endless content have left us exhausted, and why artists like Leon Thomas, Olivia Dean, and others are finding success by returning to more organic, human forms of music-making. Come for the Drake debate. Stay for the philosophy, birds, blues, and unexpected reflections on what it means to truly listen. Learn more about your ad choices. Visit megaphone.fm/adchoices See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

This week on Riffs on Riffs, we dive into “Fallin” by Chris Brown featuring Leon Thomas, and what starts as a conversation about one song quickly turns into a full-blown exploration of modern R&B, blues revivalism, AI music culture, performance authenticity, and why pain sometimes translates into great art. We unpack the cinematic weight of the song and its visual parallels to Sinners, asking whether the video is homage, influence, or something in between. We also explore how artists like Leon Thomas are helping Usher (pun intended) R&B back toward its blues roots, trading glossy perfection for something more raw, intimate, and emotionally honest. Along the way, we tackle the complicated reality of Chris Brown’s legacy. Can you separate the art from the artist? Why do some public figures become permanently polarizing while others seem to escape scrutiny entirely? Rather than offering easy answers, we sit with the tension and focus on the music itself: the harmonies, the live performance chops, the emotional weight, and the undeniable impact Chris Brown has had on modern R&B over the last two decades. The episode also veers into conversations about AI-generated music, disappearing physical media, underground mixtape culture, the return of vinyl and CDs, and why younger generations may be losing spaces where they can simply exist without being recorded. And somewhere in the middle of all that? Buddy Guy, Bruno Mars, Usher, Japanese vinyl pressings, Entourage, and the possibility that the blues are making a massive comeback. This one sprawls like a late-night jam session in a smoke-filled juke joint. Learn more about your ad choices. Visit megaphone.fm/adchoices See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In this episode of Riffs on Riffs, we unpack “Folded” by Kehlani—a song that’s equal parts breakup, late-night temptation, and emotional tug-of-war. Inspired by a shoutout from Olivia Dean, we dive into why this track has resonated so widely—and why it might not be as straightforward as it sounds. Along the way, we trace Kehlani’s journey from a turbulent childhood and early industry struggles to Grammy-winning recognition, reminding us that “overnight success” is often years in the making. We also explore the song’s musical DNA—from subtle nods to classic R&B textures reminiscent of Brandy to the orchestral flourishes that elevate it beyond a typical slow jam. But the heart of this episode lives in the tension of the lyrics: Is “Folded” a breakup song… or an invitation? A moment of closure… or the beginning of another cycle? We wrestle with the emotional reality behind lines like “come pick up your clothes,” and what they reveal about attachment, chemistry, and the stories we tell ourselves to stay connected. We also zoom out to talk about performance versus production—why live sessions (Colors, Tiny Desk, Spotify Sessions) hit differently in an AI-saturated world—and how music continues to be one of the most human forms of expression we have. And if you’ve ever considered going back to “pick up your clothes”… you might want to listen first. Learn more about your ad choices. Visit megaphone.fm/adchoices See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In this episode of Riffs on Riffs, Joe and Toby dig into “If You Don’t Want My Love” by Jalen Ngonda — a track that feels equal parts vintage and urgent. From the moment the needle drops (figuratively speaking), the conversation moves beyond the song itself and into something deeper: love, longing, and what we do when connection isn’t returned. Along the way, they unpack Ngonda’s origin story—from Maryland roots to the Liverpool Institute for Performing Arts—and explore the unmistakable texture of his sound: live instrumentation, layered harmonies, and what Toby dubs a “power falsetto.” It’s a voice that nods to legends like Sam Cooke and Marvin Gaye, but refuses to be pinned down. Joe and Toby zoom out to ask a bigger question: Why is this sound coming back now? Their answer lands somewhere between culture and craving. In a world of noise, speed, and algorithm-driven everything, this resurgence of organic, human-centered music feels less like nourishment. From Motown grooves to modern burnout, from solo concert experiences to shared moments of belonging, this episode is a meditation on connection itself. Music restores us. So whether you’re here for the riffs, the storytelling, or the search for something real…you’re in the right place!  Learn more about your ad choices. Visit megaphone.fm/adchoices See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Happy hour meets high art in this episode of Riffs, as Joe and Toby crack open a drink—and Harry Styles’ latest single, “Aperture.” What starts as a laid-back catch-up quickly unfolds into a thoughtful exploration of artistry, vulnerability, and what it really means to “let the light in.” The guys dig into Harry’s evolution from boy band phenom to genre-defying artist, unpacking how Aperture reflects a deeper creative freedom. They explore the song’s unconventional structure, its layered (and sometimes elusive) lyrics, and why Harry continues to stand apart—not because he follows the rules, but because he doesn’t seem particularly interested in them. The conversation then stretches into something bigger: the relationship between self-awareness and growth. What does it mean to “know what you don’t”? How does owning your mistakes actually set you free? And why do the most meaningful breakthroughs often come from the moments we’d rather avoid? Along the way, Joe and Toby reflect on their own experiences—friendship, failure, creative process—and connect it all back to the song’s central idea: that openness, whether to others or to yourself, is where real transformation begins. They also dive into the sound of the track itself, encouraging listeners to go beyond earbuds and truly experience the depth of modern production—because sometimes the magic isn’t just in the melody, it’s in the layers you didn’t know were there. From bourbon mishaps to philosophical insights, this episode blends humor, heart, and sharp musical perspective—reminding us that great songs open something up inside of us. Learn more about your ad choices. Visit megaphone.fm/adchoices See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In this episode of Riffs on Riffs, Joe and Toby dive into Megan Moroney’s breakout hit “Tennessee Orange.” What begins as a conversation about Moroney’s songwriting quickly expands into a lively discussion about modern country music, storytelling, and the formula behind hit songs. Joe and Toby explore the clever narrative hook at the center of “Tennessee Orange.” The song opens with a line that feels like a confession or crisis, only to reveal a far more playful “sin”: a Georgia fan falling for someone who roots for Tennessee. That twist becomes the foundation of a story that blends humor, regional culture, and the deep loyalties of SEC football rivalries. From there, the conversation expands into Moroney’s artistic approach. They discuss how her songs often follow a recognizable country-pop structure, but stand out through sharp lyrical details and relatable storytelling. They also unpack the collaborative songwriting process common in Nashville, where writers’ rooms and shared ideas help shape songs that resonate widely with audiences. Joe and Toby also compare Moroney to fellow country artist Ella Langley, discussing how each artist occupies a slightly different lane within modern country music. While Langley leans more toward a traditional country sound, Moroney’s style blends country with pop influences and carefully crafted branding. Beyond the music itself, the episode explores the broader ecosystem of the country music industry, from Nashville songwriting culture to the ways artists strategically build their public personas. As always on Riffs on Riffs, the analysis is mixed with humor, personal stories, and plenty of tangents. For Joe and Toby, “Tennessee Orange” proves that clever songwriting and strong storytelling still sit at the heart of great music. Learn more about your ad choices. Visit megaphone.fm/adchoices See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.