At 28 years old, New Milford, Connecticut native Jackson Olson has gone from chasing the traditional baseball dream to becoming one of the most recognizable faces of the Savannah Bananas — and now he’s trading Banana Ball for the ballroom on Season 35 of ‘Dancing with the Stars.’ Jackson joins us to talk about how he landed a spot on the Bananas, finding his personality as a performer in his early 20s, and the team’s mission to inject fun back into baseball. He breaks down how Banana Ball actually works, the social media machine behind the team, founders Jesse and Emily Cole’s PT Barnum-inspired approach to entertainment, his lingering MLB ambitions, and what he makes of critics — including Dave Portnoy — who think the Bananas are ruining baseball.

Then it’s time to dance. Jackson talks about partnering with Emma Slater on ‘Dancing with the Stars,’ training for five hours a day until his feet were shredded, and why learning to dance has been one of the hardest things he’s ever done. He also opens up about dealing with anxiety, using box breathing to cope, meeting Derek Hough, and setting his sights on the Mirrorball Trophy. Plus, we get into kids dressing up as him for Halloween, John Cena and Kristen Bell, his love of Hugh Jackman and ‘The Greatest Showman,’ becoming a very late musical-theater convert, his relationship with Maggie Sajak, why he wants kids watching him to feel free to show a little more personality, and so much more.

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Too $hort joins us to look back on more than four decades in hip-hop and the stories behind one of the genre’s most enduring careers. He takes us back to Oakland in the ’80s, when he was selling $20 custom raps on cassette to local drug dealers, and explains how his voice and name became famous around the Bay Area before people even knew what he looked like. He also gets into the stories behind songs like “Freaky Tales” and “Blowjob Betty,” his mother’s reaction to his music, the meaning of being a “player,” and why his supposed retirement in 1996 was never quite what it seemed.

Now 60 years old and still going strong, he breaks down his place in hip-hop history, from the ’90s East Coast–West Coast rivalry and the rise of hyphy to the Lil Jon collaboration that changed the course of his career and the making of “Blow the Whistle.” Too $hort shares what it was like recording with The Notorious B.I.G., Tupac and JAY-Z (the only rapper to do so!), including watching Biggie work without writing down his verses and the incredible speed of Tupac’s process. Plus, he talks working with Snow Tha Product, forming Mount Westmore with Snoop Dogg, Ice Cube and E-40, becoming a father later in life, and so much more.

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AWICH and ONE OK ROCK frontman Taka join us to introduce YAO, the new Japanese supergroup bringing together AWICH, ONE OK ROCK, CHICO CARLITO and Paledusk. They explain how the collective came together, the Japanese philosophy behind its name, spending a month in Biarritz creating together and the story behind debut single “777.” Plus, working with RZA, JAY-Z and Linkin Park, and the differences between Japanese and American artists.

AWICH opens up about growing up in Okinawa, writing poetry, becoming a rapper at 14, moving to America, motherhood and returning home after the death of her daughter’s father. Meanwhile, Taka reflects on growing up with two famous singers as parents, facing assumptions about his success, getting kicked out of J-pop group NEWS and eventually becoming the frontman of ONE OK ROCK. Plus, learning English, why Taka once planned to quit at 35, Ed Sheeran at the Sphere, Backstreet Boys, Vegas, and taking Japanese music global.

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The Warning join us in the studio for a second time to discuss their fifth album, Everything's Falling. Hailing from Monterrey, Mexico, sisters Daniela, Paulina and Alejandra Villarreal stop in fresh from Japan to talk about making the record, taking six months off the road to process the past five years, and what they've learned after 13 years together as a band. We also get into why they write in English, how Monterrey still comes through in their music, and the ways they've continued to get to know each other through the songs they make.

Plus, we dig into the specific songs on the record, from catastrophic thoughts and industry tunnel vision to growing up in public and the double standards still being felt for women in rock. The sisters also discuss fear of dying, the influence of Sean Paul, which of them is the most opinionated and confrontational, getting back on the road, and so much more.

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The legend that is Sara Bareilles joins us to talk about ‘Good Grief,’ her first album in seven years, and the new documentary of the same name. She opens up about navigating some incredibly difficult years, and the tenderness, humor and humility she’s found along the way. During that time, she’s said goodbye to several close friends while also embarking on IVF, and she’s open in her music — and in person — about the complicated emotions that can accompany the path to parenthood. The documentary captures the intimate recording of the album in Woodstock, NY, with her close collaborators, alongside incredibly candid conversations exploring many of the same themes. She also discusses the story behind the song “Home,” which was inspired by a podcast conversation between Anderson Cooper and Stephen Colbert about Colbert losing his father and two brothers when he was just 10 years old.

Sara also looks back at the songs and projects that have shaped her career, from “Gravity” and “Brave” to “Love Song”; the origins of ‘Waitress’ and what writing musical theater taught her about collaboration; and her connection to poet and activist Andrea Gibson, both in song and through the documentary ‘Come See Me in the Good Light.’ Kelsey pops in to go deep on Sara’s hilarious Netflix show ‘Girls5eva,’ and Sara leaves us with some real food for thought: the idea at the heart of ‘Good Grief’ is that the life you have isn’t somewhere else waiting for you — you have to wake up to the one you’re already living.

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Owen Thiele has stories for days. We could have kept him chin-wagging on the couch for another hour, but the actor, podcaster, and all around hilarious human stopped by primarily to talk about the hotly anticipated second season of ‘Adults,’ which, by the way, blows season 1 out of the water.

We discuss the show in-depth, working with his now-bestie castmates and the arc of Anton’s story, not to mention the entrance of Raven Symone as his sister (and the cultural importance of ‘That’s So Raven.’ But then things get really good: there’s talk of peptides, SoulCyle sharting, his fascinating childhood and family history — from his adoption story, to his mom as his best bud, to his star-studded LA high school — and just what is going on with his in-development series ‘Off Color’ based on his real life. And of course we get into his podcast, ‘In Your Dreams’ (Alex Cooper made him do it), his long-term love with iconic stylist-to-the-stars Jared, staying friends with exes, going to NYU with Timothée Chalamet, appearing in an Almay commercial as Rashida Jones’ assistant, and so much more.

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Maia Reficco and Fernando Lindez join us to discuss their new Prime Video romance ‘The Last Sunrise,’ based on the novel by Anna Todd. Maia stars as Ry, a college student living with a chronic illness who heads to Mallorca with her protective mother, played by Eva Longoria, and unexpectedly falls for local Julián, played by Fernando. Maia comes to the film after starring in ‘Pretty Little Liars: Original Sin’ and making her mark on Broadway in ‘Hadestown,’ while Spanish actor and model Fernando brings a very different path to the couch — from being discovered in the background of a friend’s Instagram photo at 18 to opening a Versace show in Milan.

They talk about their bad first impressions to building a genuine closeness while filming in Mallorca, intimacy coordination, the logistics of Fernando’s nude scene, (and his love of nude beaches!), and what it was like having Eva Longoria play Maia’s mom. They also unpack the film’s bigger ideas about romance, family, and how fleeting life can be.

Plus, Maia talks about her Argentine identity, her Nickelodeon past, meeting Lionel Messi, and the importance of queer representation and queer characters existing without being tokenized. Fernando opens up about playing a gay character in ‘Elite,’ the loneliness and relentlessness of his early modeling years, and why Julián might be more like him than he expected.

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At just 19 years old, Chino Pacas has already released three LPs: 'Que Sigan Llegando las Pacas' (2024), 'CRISTIAN' (2025), and now 'QSLLP V2' — a record inspired in part by John Wick. His music is yet another reason why corridos are going global and reaching new, younger audiences. He joins us on the couch for the first time to talk about his beginnings in Mexico, the essential influence of his brother Turo, moving to Florida, going viral on TikTok, and getting discovered and signed by JOP. Oh, and then there was that lil’ collab with Drake.

Plus, he discusses collaborating with FLVCKKA, wanting to experiment with bachata and cumbia — and eventually record in English — how he wound up buying a fan a Louis Vuitton bag, why “gorditas is my thing,” and so much more.

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After having Nick and Chris on the show over the years we finally bag Matt who has something he’s super proud to talk about: his memoir ‘What Happened Yesterday.’ The 23-year-old opens up about growing up as a triplet with Nick and Chris and the complicated process of figuring out who he is outside of his brothers after spending much of their lives having practically identical experiences. Plus, how the three have learned to create together while building increasingly independent lives.

Primarily though, his memoir is a candid portrayal of his experiences living with debilitating anxiety, his mental health and medication journey, not to mention therapy. He discusses the loss of his grandad, family issues, panic attacks, and how writing has become an outlet and a boon.

We also discuss the adrenaline rush of the Sturniolo Triplets’ rapid YouTube success, social media and public perception, and why he wants to talk openly about mental health while keeping some parts of his life — including his relationships — completely private. Oh! And his utter lack of FOMO, why Nick still can’t drive, Dunkin’ vs. Starbucks, asking Madison Beer for memoir-writing advice, and so much more.

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Harry Jowsey returns to discuss his new Netflix show ‘Let’s Marry Harry,’ where 20 women are competing for his heart as he searches for a wife with help from friends Amanda Kloots, Sony Henty, and his ex Georgia Hassarati. Alex Cooper also pops in with her two cents.

The Aussie-born reality TV bad boy and heartthrob has become a reality TV regular (watch out for him on ‘The Mob’ this Fall) since his 2020 break out moment on 2020’s ‘Too Hot to Handle.’ He’s since expanded into podcasting (‘Boyfriend Material’), hosting, producing, and even acting (in a film with Al Pacino?! Yeah really!). Oh and he has his own skincare brand which he founded after several skin cancer scares.

On this ep Harry opens up about losing his dad through assisted dying, continuing to navigate his grief, and how that experience reshaped the way he thinks about commitment, monogamy, and what he wants from a partner. He also talks about sobriety, his relationship with alcohol, his infamous dating history, and what it’s been like trying to grow out of the “reality TV bad boy” label while still living a very public life. Plus, he gets into what really happens behind the scenes of reality TV, looksmaxxing, OnlyFans, and why ‘Let’s Marry Harry’ is one of the first projects he feels genuinely proud of.

Has Harry finally graduated from boyf material to hubby material? See what you think.

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