It was a real magic moment to connect with Aimee Mann, a musician I’ve listened to for decades. She indulges my curiosities about lyric choices and instrumental training, and I learn how much goes on behind the scenes of an Aimee Mann production. We talk about the traumas of her past, which hardships do and do not influence her work, and why there feels like a creative imperative to turn pain into art. Then, to lighten things up (at least a little) we bond over some of our favorite artists of years past, like the sneakily somber Steely Dan.
Gillian Anderson and I share a connection unlike any other. The Dana Scully to my Fox Mulder, we are the only ones who understand what the other was going through during those X-Files years. But so much was left unsaid — until now. We got a chance to open up about the ways we might have failed one another during that wild ride, and we both examine the ways we’ve grown since. Gillian also caught me up on all her ventures and adventures — her work, her writing in the sexual fantasy compilation Want, and her cheeky new “unconventional wellness” line of soft drinks. It’s good to rediscover an old friend.
Jia Tolentino has the internet to thank for some of her biggest successes. In the 2000s, it offered her connections beyond her strict religious community and gave her a place to share her writing with her millennial peers. Her “online” insights carved out a niche at The New Yorker, and her 2019 essay collection, Trick Mirror: Reflections on Self-Delusion, made a big splash with readers who felt similarly mired in digital disillusion. But these days she’s swearing off social media and seeking out the sublime elsewhere. Jia and I discuss the joys and perils of living life online (or even adjacent to it), the unexpected impacts of digital surveillance, and what all of this means for raising children.
Nate Silver is a risk taker. On top of boldly and publicly forecasting elections as part of his website FiveThirtyEight, he’s a regular poker player, and in just one season of basketball, he bet nearly 2 million dollars on games. He still doesn’t have the foolproof winning formula figured out – even though that’s the ultimate forecaster’s promise – but that doesn’t mean I wouldn’t bet on him, or along with him. I have no interest in Vegas, but I can still apply Nate’s life lessons about how to work hard, ask the right questions, and embrace failure as information.
I’ve known Jason Beghe for 50 years and counting, ever since we met one fateful day in a high school biology class. I watched as this rambunctious and rebellious kid grew up and carved his own path, never following trends. But when Jason became heavily involved in the Church of Scientology, we drifted apart — and I felt like I’d failed him as a friend. For the first time, we unpack what went on between us during that period of our lives, and why our friendship endured. These days we’re close as ever, and I couldn’t be more proud of Jason’s unparalleled success as Sgt. Hank Voight on the long-running NBC series Chicago P.D. From the halls of our high school to the set of Californication, we reflect on a lifelong friendship the same way we always have: with heart and lots of childlike laughter.
Rosie O’Donnell’s famous friends tell her she’s no good at being a celebrity. And if she’s honest, she’s never really felt like one. Despite her iconic roles and mass appeal, Rosie says she always identified more with the viewers at home rather than the stars she was interviewing on her long-running talk show. We got together in person to discuss all this, plus the devastating loss she suffered as a child, and what we both think about meeting fans at conventions. Rosie might feel iffy about fame, but that doesn’t mean the “it” factor that propelled her there isn’t still a driving force in her creative and personal life. And she’s continued to inspire others, too — just ask Eminem.
Lisa Loeb has the mind of a student — a straight-A, Grammy-winning student. As we talk, she moves between earnest curiosity and a dogged determination to succeed, and it’s clear to me that Lisa’s robust musical career (extending way beyond her hit song “Stay (I Missed You)”) has a lot to do with how hard she fought to open the doors that were closed on her. From less than ideal musical collaborations to the iffy vicissitudes of press, Lisa knows conflict when she sees it. And while she doesn’t necessarily embrace these challenges, she knows she learns a hell of a lot once she reaches the other side.
When a young Andy Cohen sat in front of his family’s TV watching hours and hours of soap operas, his mother grew increasingly concerned about his future: Was he destined to become an “airhead”? But Andy’s obsession with melodrama paid off. He’s defined modern television as executive producer of the Real Housewives reality show franchise, and he’s spent 15 years as the host of the boundary-pushing talk show Watch What Happens Live. We discuss the little moments that could have changed everything for Andy, how he decides what to share and keep private, and why he has so much respect for actors — and I for reality show editors.
As a veteran late-night guest, I know a phony host when I see one — and Seth Meyers is as genuine as they come. He’s been a professional funny guy on TV for decades, first joining the cast of Saturday Night Live in 2001, then hosting his own late-night talk show since 2014. Over the years, he’s learned the hard way what works and what doesn’t, stumbling through creative missteps in front of millions of people and, even worse, in front of Lorne Michaels. We discuss standout skits, the legacy of late night, and how having good taste often means knowing when to step aside.
Here’s something a little different this week, before I come back next week with more interviews. At the end of each episode, you hear a snippet of my thoughts on the interview, usually a day or so later after I’ve had time to sit with it. I share the full version of those freeform, reflective monologues with our Premium subscribers, and today I wanted to share some of my favorites to give you a glimpse.