Actor, writer, economist, and lawyer Ben Stein joins Chelsea to discuss his iconic acting role on Ferris Bueller's Day Off, hosting Win Ben Stein's Money, writing speeches for Nixon, meeting his wife, being wealthy, and much more.
Comedian Earl Skakel sits down with Chelsea to relate his experience acting on I’m Dying Up Here, growing up amongst the Hollywood elite, getting metoo’d, dressing to impress, navigating social and professional dynamics at The Comedy Store, visiting “massage parlors”, and more.
Chelsea and actress Molly Tarlov, of MTV's Awkward, discuss the paranormal, attending strip clubs with a significant other, crystals, tarot cards, wedding planning, phobias, Halloween costumes, spas and more.
Chelsea sits down with comedian, techie and podcast producer Brian Redban, detailing his instrumental roles behind the scenes at The Comedy Store, producing The Joe Rogan Experience, and creating the Deathsquad podcast network. Among many other things, they discuss phobias, dieting, Chelsea’s bizarre food aversions, and simulation theory
Comedian Sara Weinshenk joins Chelsea to discuss her (and her dad’s) fashion sense, musicals, vulnerability vs. shame, Esther Hicks, Dr. Pat Allen and other self-help gurus, writing, Mac Miller, and much more.
Nicholaus Goossen, director of Grandma’s Boy, joins Chelsea to discuss DNA, Chelsea’s wedding, growing up in a boxing gym, working with Adam Sandler, and various ins and outs of film directing and screenwriting.
Writer, musician, and television personality Nick Simmons talks to Chelsea about his life on reality TV with his father, KISS frontman Gene Simmons, AKA The Demon. They discuss stand-up comedy, the tongue myth, going through teenage years on television, Nick’s writing for Vice and the Huffington Post, and much more.
Instagram and Twitter: @NickTSimmons
Musician Dave Navarro joins Chelsea to share his views on meditation, social media, dating apps, yoga, sobriety, trauma therapy, ayahuasca, body suspension and marriage advice.
Comedian, actress and model Kate Quigley sits down with Chelsea to talk about hosting, hecklers, "edgy" jokes, crowd work, morning radio, hookups on the road, hosting the Playboy Channel's Undercover, sex in public, hosting the AVN Awards, and what it’s like dating a porn star.
Hanna Dickinson, comedian and writer for Comedy Central's Comedy Knockout, lounges around in a robe, chatting with Chelsea before she hosts the red carpet of the Bruce Willis Roast, standup performance and booking, therapy, Chelsea's upcoming wedding, birth control and much more.
Writer/actor/director/boxer Justin Gilbert tells Chelsea all about his time growing up with wild people in Oklahoma, being the Comedy Store security guard, a celebrity bodyguard, living in the slums of Los Angeles, and more.
Chelsea sits down with artist Julia Fox to discuss Julia’s past experience with drug addiction, being a dominatrix, domestic violence, growing up in Italy, staging her own funeral, making a film about Reno sex trafficking, and manifesting goals.
Chelsea chats with writer/comedian Andrew about his upbringing in Colorado, moving to Los Angeles, talk therapy, romantic relationships, auditioning, Hereditary, meditation, Chelsea's childhood anorexia & much more.
Chelsea talks with transgender actor and reality TV star Cassandra Cass about her journey from Iowa boy to Hollywood lady, discussing her gradual shift in identity, family relations, breaking into show business, trans surgery and anatomy, anal sex tips, dating, and much more.
Actor, writer, director, comedian and visual artist Andre Hyland joins Chelsea to reminisce about his childhood assaults on teachers, being kicked out of multiple schools, adolescent video productions and graffiti, leading up to more recent creative exploits including a documentary, creating his character Jesse Miller, getting a short into Sundance, and much more.
Chelsea and defiantly unique comedian Brent Weinbach discuss the intricacies of water, dental care, cell phones, pranks, fashion, germs, hugging, pets, dancing, comedy and more.
Chelsea and fashion designer Laura Sfez, of L’ecole des Femmes, discuss Laura’s teenage expatriatism, how she created her own clothing line, writing, confidence, uniform fetishism, inspiration and creativity, the key to dressing sexy while still being elegant, and why it’s better to shoot with female photographers.
Playboy journalist and comic Bridget Phetasy tells all about her unbelievable experiences in the Osho sex cult (as seen in the Netflix series Wild Wild Country) as well as forays into orgasmic meditation and other shady new age brainwashing schemes.