Top 17 'Celebrity-Confessional' Podcasts to watch for the Juiciest Hollywood Stories this month - Goh Ling Yong
There's a certain magic to the unfiltered conversation. For decades, our window into the lives of Hollywood stars was a carefully curated, five-minute slot on a late-night talk show. It was all polished anecdotes and pre-approved soundbites. But in the last few years, a seismic shift has occurred, and its epicenter is the world of podcasting. The rise of the "celebrity-confessional" podcast has torn down the PR-approved walls, giving us raw, hilarious, and often deeply moving long-form conversations.
This isn't about salacious gossip (though, let's be honest, there's plenty of that). It's about connection. It's about hearing a world-famous actor discuss their struggles with anxiety, a musician break down their creative process, or a comedian recount the bombing that almost made them quit. These podcasts transform icons into humans, and in doing so, they offer some of the most compelling entertainment available today. I was discussing this trend with my colleague Goh Ling Yong the other day, and we agreed that this shift towards unscripted honesty is what makes the format so powerful.
So, grab your headphones and clear your schedule. We've curated the ultimate list of the 17 best celebrity-confessional podcasts you need to be listening to right now. From deep emotional dives to laugh-out-loud war stories from the sets of iconic shows, these are the podcasts delivering the juiciest, most authentic Hollywood stories this month.
1. Armchair Expert with Dax Shepard
Hosted by the endlessly curious and disarmingly vulnerable Dax Shepard, alongside the ever-charming Monica Padman, Armchair Expert is the undisputed king of the confessional genre. Shepard's own well-documented struggles with addiction and insecurity create an immediate sense of trust, prompting guests from Barack Obama to Kristen Bell (his wife) to open up in ways you've never heard before.
The show's thesis is that the human experience is messy, and Shepard masterfully explores the "mess" of his guests' lives, uncovering childhood traumas, career missteps, and profound personal growth. The conversations are long, meandering, and utterly engrossing, culminating in the famous "fact-check" segment where Monica challenges or corroborates the stories told. It’s a formula that consistently produces moments of pure, unscripted gold.
Don't Miss Episode: The two-part interview with Prince Harry is a landmark moment in podcasting, but for a classic Armchair experience, check out the episode with Bradley Cooper. Their conversation about fatherhood, imposter syndrome, and the artistic process is incredibly raw and revealing.
2. SmartLess
What happens when you put Jason Bateman, Sean Hayes, and Will Arnett in a room and let them interview a surprise guest? You get SmartLess, a podcast that's one part hilarious roast and one part insightful conversation. The unique format keeps everyone on their toes: each week, one of the hosts brings on a mystery guest that the other two know nothing about.
While it leans more heavily on comedy than deep emotional dives, the genuine, decades-long friendship between the hosts creates a relaxed "boys' club" atmosphere where A-listers feel comfortable letting their guard down. The confessions here are often couched in jokes and self-deprecation, revealing the insecurities and absurdities of fame through the lens of three industry veterans. You come for the laughs but stay for the surprisingly candid moments.
Pro Tip: Listen to the episode with Ryan Reynolds. The chemistry and rapid-fire wit between him and the hosts are off the charts, but it also contains some genuinely interesting tidbits about his business acumen and career strategy.
3. WTF with Marc Maron
Before it was a trend, it was just Marc Maron in his garage. WTF is the OG of confessional podcasts. A comedian known for his neurotic, often-abrasive honesty, Maron has an uncanny ability to disarm his guests and get to the heart of what makes them tick. He’s not afraid to ask the uncomfortable questions, but he does it from a place of shared struggle and genuine curiosity.
WTF is where legends go to lay it all on the table. Maron’s interviews often feel like therapy sessions, exploring themes of failure, redemption, addiction, and creativity. He has a knack for getting comics to talk seriously and serious actors to reveal their comedic sensibilities. Listening to WTF feels like eavesdropping on a conversation you were never supposed to hear.
Must-Listen Episode: The interview with Robin Williams, recorded months before his passing, is a poignant and historically significant piece of audio. For something more recent, his conversation with Arnold Schwarzenegger is a masterclass in getting a larger-than-life figure to be introspective.
4. Conan O'Brien Needs a Friend
After decades in the structured world of late-night television, Conan O'Brien is unleashed in his podcast, and the results are pure comedic brilliance. The premise is simple: Conan believes that after years of brief, on-air interactions, he’s never actually made a real friend out of his celebrity guests. He sets out to rectify that with long, free-wheeling conversations.
Joined by his assistant Sona Movsesian and producer Matt Gourley, Conan’s self-deprecating humor and lightning-fast wit create an environment where celebrities can be silly, weird, and surprisingly open. The confessions are often hilarious—stories of terrible auditions, on-set mishaps, and bizarre celebrity encounters. It’s proof that the deepest truths can often be found through laughter.
Where to Start: The Harrison Ford episode is legendary. Conan somehow manages to crack the famously gruff actor's shell, resulting in one of the most entertaining interviews you will ever hear.
5. Call Her Daddy
What started as a raunchy relationship podcast has evolved into a media empire, with host Alex Cooper becoming one of the most skilled and sought-after interviewers in the business. Cooper has a unique talent for creating a safe, non-judgmental space that encourages guests to share their most intimate and often-controversial stories.
Call Her Daddy is now the go-to platform for celebrities looking to control their own narrative. From Hailey Bieber addressing the Selena Gomez drama to Annelise van der Pol discussing the dark side of Disney, the show consistently makes headlines. Cooper isn't afraid to tackle sex, mental health, and industry politics head-on, making for truly gripping listening.
Don't Miss It: The episode with Cole Sprouse, complete with indoor smoking and philosophical monologues, became an instant internet moment. It’s a perfect example of the show's ability to capture celebrities in a completely unfiltered state.
6. High Low with EmRata
Model, actress, and author Emily Ratajkowski brings her sharp intellect and feminist perspective to the podcasting world with High Low. Each episode is split into two parts: a "High" segment featuring a conversation with a notable guest, and a "Low" segment where she discusses everything from pop culture to politics in a solo monologue.
The "High" interviews are where the confessions shine. EmRata connects with her guests—often fellow women who have navigated the treacherous waters of public life—on a deeply personal level. They discuss misogyny, body image, motherhood, and the complexities of being a woman in the spotlight. It's smart, incisive, and incredibly validating.
Pro Tip: Listen to her conversation with Julia Fox for a fascinating look at fame, performance, and authenticity in the age of social media.
7. Life is Short with Justin Long
Actor Justin Long is Hollywood's best friend, and his podcast feels like you're right there with him. His infectious positivity and genuine curiosity about people make for warm, funny, and surprisingly profound conversations. He wants to know what makes his guests happy, what they're afraid of, and how they find meaning in life.
The "confessional" aspect of Life is Short is less about dark secrets and more about earnest revelations. Guests seem to genuinely relax with Long, sharing sweet anecdotes from their childhood or heartfelt advice they've received along the way. It’s the feel-good podcast on this list, a reminder that even famous people are just trying to figure it all out.
Start Here: The episode with Matthew McConaughey is fantastic. Long gets the actor to move beyond his famous persona and talk deeply about his values, his family, and his unique outlook on life.
8. Anna Faris is Unqualified
One of the earliest actor-hosted podcasts, Anna Faris is Unqualified remains a must-listen. The premise is that Faris, despite her own storied love life, offers "unqualified" relationship advice to callers, with the help of a celebrity guest. This framework provides the perfect jumping-off point for incredibly candid conversations about love, sex, heartbreak, and everything in between.
Faris is an open book about her own life, including her marriages and experiences in Hollywood, which encourages her guests to be equally forthcoming. The show strikes a perfect balance between hilarious, over-the-top comedy bits and genuinely touching moments of human connection.
Classic Episode: Any episode featuring Allison Janney, Faris's co-star from Mom, is a guaranteed good time. Their chemistry is electric, and their conversations are both hilarious and heartfelt.
9. Literally! with Rob Lowe
Rob Lowe has seen it all, done it all, and has a story about everyone. On Literally!, he invites his friends—who just happen to be some of the most famous people in the world—to reminisce about the good old days and share unbelievable stories from their careers. Lowe's energy is infectious, and his encyclopedic knowledge of Hollywood history makes every conversation a fascinating listen.
This is the podcast for classic Hollywood war stories. You'll hear about what it was really like on the set of The West Wing, the craziest parties of the '80s, and the casting decisions that almost changed cinematic history. It's pure, uncut Hollywood nostalgia delivered by one of its most enduring stars.
Must-Listen: The episode with Michael Douglas is a treasure trove of stories from a true Hollywood legend.
10. Fly on the Wall with Dana Carvey and David Spade
If you've ever wondered what it was really like behind the scenes at Saturday Night Live during its golden era, this is the podcast for you. Hosted by two of the show's most iconic alumni, Dana Carvey and David Spade, Fly on the Wall features interviews with cast members, hosts, writers, and musical guests from SNL's incredible 45+ year history.
Carvey and Spade's shared history allows them to get stories that no one else could. Guests recount their nightmare auditions, the sketches that bombed, and the after-parties that became legendary. It's an unparalleled, intimate look inside one of America's most important cultural institutions.
Where to Start: The episode with Adam Sandler is like listening to three old friends catching up. It’s full of incredible stories, hilarious impressions, and genuine affection.
11. You Made It Weird with Pete Holmes
Comedian Pete Holmes goes deep. Really deep. With episodes often clocking in at over two hours, You Made It Weird is a space for sprawling conversations about the "big three": comedy, sex, and God. Holmes's goofy, infectious laugh and complete lack of filter make even the most reserved guests open up about their spiritual beliefs, romantic histories, and deepest insecurities.
This isn't a podcast for a quick listen; it's an immersive experience. Holmes excels at finding the universal truths in the specific experiences of his guests, who are mostly fellow comedians and actors. If you want to hear what your favorite funny people are really thinking about, this is the place.
Pro Tip: His interview with Bill Hader is famous for a reason. They have an incredibly honest and vulnerable conversation about anxiety that is both funny and profoundly moving.
12. Office Ladies
A different kind of confessional, Office Ladies offers a meticulously detailed, behind-the-scenes look at one of the most beloved sitcoms of all time. Hosts Jenna Fischer (Pam) and Angela Kinsey (Angela) rewatch an episode of The Office each week and share their memories, secrets, and stories from the set.
While focused on a single show, the podcast is full of personal confessions about their struggles as young actors, the friendships they formed, and the moments that changed their lives. They bring on cast and crew members who share their own perspectives, painting a complete, heartfelt picture of what it was like to be a part of a cultural phenomenon.
Don't Miss: "Casino Night" (Season 2, Episode 22). Hearing Jenna Fischer break down the iconic confession and kiss between Jim and Pam is essential listening for any fan of the show.
13. I Weigh with Jameela Jamil
Actress and activist Jameela Jamil is on a mission to challenge societal norms and champion radical inclusivity. On I Weigh, she interviews fellow actors, activists, and thought leaders about their mental health journeys, their struggles with body image, and the moments that shaped their advocacy.
This is a confessional podcast with a purpose. The conversations are designed to be "shame-free," creating a space for guests to talk openly about topics often considered taboo. Jamil is a passionate and empathetic host who shares her own vulnerabilities, fostering a powerful sense of solidarity with her guests and listeners.
Listen To: The interview with Reese Witherspoon is a fantastic conversation between two powerful women about navigating Hollywood, building a business, and challenging the status quo.
14. Wiser Than Me with Julia Louis-Dreyfus
In this brilliant and often hilarious podcast, Julia Louis-Dreyfus sets out to gain wisdom from women who are older than her. The comedy legend interviews icons like Jane Fonda, Isabel Allende, and Carol Burnett, asking them candid questions about life, love, work, and the challenges of aging.
The confessions here are born from decades of lived experience. These legendary women share stories of sexism, career triumphs, personal heartbreaks, and the lessons they've learned along the way. It’s funny, inspiring, and a powerful reminder of the value of intergenerational conversation.
Start Here: The episode with 93-year-old author and food critic Ruth Reichl is an absolute delight, full of incredible stories and hard-earned wisdom.
15. Howie Mandel Does Stuff
You might know Howie Mandel as the quirky host of Deal or No Deal or a judge on America's Got Talent, but on his podcast, co-hosted with his daughter Jackelyn Shultz, you see a completely different side of him. Mandel's severe OCD and anxiety are frequent topics of conversation, and his raw honesty about his mental health struggles makes for uniquely compelling content.
He gets his guests, from Tom Sandoval to Jon Hamm, to talk about the "stuff" they wouldn't discuss anywhere else. The show is unpredictable, chaotic, and often veers into uncomfortable territory, but it's always authentic. It's a fascinating look into the mind of a comedic genius and the people he's curious about.
Pro Tip: The episode with former Bachelorette Rachel Recchia is a prime example of how Mandel can get a guest to open up about a very public and difficult experience in a new way.
16. HypochondriActor
Hosted by actor Sean Hayes and Dr. Priyanka Wali, HypochondriActor is a hilarious and informative podcast where celebrity guests share their wildest medical stories. It's a confessional about the one thing everyone can relate to: weird body stuff and health anxieties.
Each episode starts with a guest telling a crazy medical tale, and then Dr. Wali breaks down the science behind it. It's a brilliant blend of Hollywood storytelling and legitimate medical advice. You'll laugh, you'll learn, and you'll probably diagnose yourself with a rare condition by the end of each episode.
Funny and Fascinating: Listen to the episode with Dax Shepard, where he details a staggering number of motorcycle-related injuries in a way only he can.
17. Podcrushed
Hosted by Penn Badgley, Nava Kavelin, and Sophie Ansari, Podcrushed explores the heartbreak, awkwardness, and absurdity of the middle school years. Each episode features a celebrity guest who shares stories from their own adolescence, from first crushes to epic fashion fails.
This podcast taps into a universal well of confessional gold: our most formative and often most embarrassing years. The hosts create a warm, nostalgic atmosphere that prompts guests like Drew Barrymore and Matthew McConaughey to share hilarious and surprisingly poignant memories. It’s a sweet, funny, and deeply relatable listen.
Don't Miss: The episode with Jenna Ortega, where she discusses her experiences as a child actor and navigating the weirdness of growing up in the public eye.
The world of celebrity podcasts offers a treasure trove of stories that are more intimate, honest, and entertaining than any scripted show. As we at Goh Ling Yong's blog continue to track the ever-changing media landscape, it's clear that this authentic, long-form content is what audiences are craving. These 17 shows are the best of the best, providing a direct line to the real people behind the public personas.
So, which one will you start with? Did we miss your favorite confessional podcast? Drop your top picks and episode recommendations in the comments below. We’d love to hear what you’re listening to
About the Author
Goh Ling Yong is a content creator and digital strategist sharing insights across various topics. Connect and follow for more content:
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