Legendary broadcast journalist Katie Couric joins our final episode to share lessons she's learned from her extraordinary career. Katie tells Brooke how she responded when CNN’s president questioned her talent, what she took from her history-making turn at CBS Evening News, and how she fought to shake the “morning news albatross.” Speaking candidly about the lingering pain from her husband and sister’s deaths, Katie also shares how standing up to cancer has become her life’s mission.See omnystudio.com/listener for privacy information.

Brooke’s hubby Chris Henchy makes his “Now What?” debut! The couple swap details about their meet-cute on the Warner Brothers lot, their parenting skills and favorite family traditions, and how Chris’ dedication to his Irish granny helped convince Brooke he was "the one." Chris also opens up about his journey from finance bro to comedy writer, and shares how he moved on from the failure of his first movie to one of his greatest successes to date.See omnystudio.com/listener for privacy information.

Writer, director, and actress Jennifer Esposito stops by to talk about her critically acclaimed new film, Fresh Kills, and shares how making her dream project helped her heal from years of abuse from industry heavyweights. Brooke and Jennifer discuss the importance of self-advocacy, Jennifer’s life-long struggle with celiac disease, and the power of art to breed greater empathy and understanding.See omnystudio.com/listener for privacy information.

Author, advice columnist, and all-around badass Cheryl Strayed joins Brooke for a wide-ranging conversation about parenting, childhood poverty, and what it means to be rich in love. Cheryl gets candid about the years leading up to her famous trek on the Pacific Crest Trail, and shares why she’s in need of another life-changing journey. Plus, the one thing Cheryl keeps in mind whenever she gives advice.See omnystudio.com/listener for privacy information.

Neurosurgeon, podcast host, and CNN’s Chief Medical Correspondent Dr. Sanjay Gupta chats with Brooke about why some brains respond more positively to “now what” moments than others, what his mom’s refugee journey taught him about resilience, and why his pivot into broadcasting was one of the biggest challenges of his life. Plus, Brooke and Sanjay share the advice they’d give their 25-year-old selves.See omnystudio.com/listener for privacy information.

Singer, songwriter, and activist Joan Baez chats with Brooke about her new documentary “I Am Noise,” and shares why she chose now to reveal intimate new details about her personal life and music. Joan also reflects on some of the biggest moments of her 60-year career (including her performance at The March on Washington), how our voices shape our identity, and what it means to be courageous.See omnystudio.com/listener for privacy information.

Cedric the Entertainer chats with Brooke about his new novel Flipping Boxcars, the origins of his "dapper style," and his pre-comedy career at State Farm. Cedric also opens up about how the industry has evolved for non-white performers and shares why he pivoted his career to be closer to his family.See omnystudio.com/listener for privacy information.

Have mercy! John Stamos and Brooke take a trip down memory lane as they reminisce about their young Hollywood days and their struggle to find legitimacy as actors. John opens up about his early “hatred” of Full House, his past alcohol addiction, and how love letters from his parents inspired him to write a memoir.See omnystudio.com/listener for privacy information.

Actress and comedian Sarah Silverman bonds with Brooke over their own parents' "sick" sense of humor, and discusses how her struggle with bedwetting as a kid made her less afraid of bombing onstage. Sarah also talks about the comedy boy’s club of the '90s, the evolution of her own material, and how aging forced her to embrace "the other parts" of herself.See omnystudio.com/listener for privacy information.

Brooke’s good friend and long-lost brother Willie Geist (Morning Joe, Sunday Today) joins the pod and shares the ways in which living in the South for 10 years changed his worldview, the moment he got (and then subsequently lost) a dream job, and what his father’s Parkinson’s diagnosis taught him about gratitude. Brooke and Willie reminisce about the origins of their friendship, including the show-stopping way Brooke first met his family (spoiler: it involves theft.)See omnystudio.com/listener for privacy information.