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The Nightly
Category Is: Sleep w/ Bob The Drag Queen
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Wils Pelton and Josh Gondelman welcome Bob the Drag Queen for a surprisingly heartfelt late-night chat about Broadway, stand-up comedy, internet outrage, and whether the universe actually cares about any of us.
What You’ll Hear
Broadway Dreams, Broadway Schedules: Bob reflects on performing in Moulin Rouge, surviving eight shows a week, and why exhausting experiences can still feel deeply worth it.
The Internet Is Yelling Again: A conversation about accidental AI art drama, public scrutiny, and the strange emotional math of being perceived online by millions of strangers.
Karma, Nihilism, and Bedtime Thoughts: The trio wanders into a warm existential detour about meaning, bad luck, grief, and the tiny frameworks people build to get through the day.
CHAPTERS
00:00 Intro & Bob the Drag Queen arrives
01:45 Broadway life and Moulin Rouge
05:45 Building a stand-up tour
09:00 Reality TV and staying authentic
12:30 AI poster backlash and internet outrage
16:00 Karma, grief, and existential bedtime thoughts
19:20 Good nights and six-fingered posters
What You’ll Hear
Broadway Dreams, Broadway Schedules: Bob reflects on performing in Moulin Rouge, surviving eight shows a week, and why exhausting experiences can still feel deeply worth it.
The Internet Is Yelling Again: A conversation about accidental AI art drama, public scrutiny, and the strange emotional math of being perceived online by millions of strangers.
Karma, Nihilism, and Bedtime Thoughts: The trio wanders into a warm existential detour about meaning, bad luck, grief, and the tiny frameworks people build to get through the day.
CHAPTERS
00:00 Intro & Bob the Drag Queen arrives
01:45 Broadway life and Moulin Rouge
05:45 Building a stand-up tour
09:00 Reality TV and staying authentic
12:30 AI poster backlash and internet outrage
16:00 Karma, grief, and existential bedtime thoughts
19:20 Good nights and six-fingered posters
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More episodes
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Finally, An Umbrella She Loves
28:43|Josh Gondelman talks with Caller Sarah about embracing daylight saving time, finding the clear umbrella that changed her rainy days, and feeding peanuts to a flock of blue jays.What You'll Hear:Sweater Weather Math: Josh opens with his yearly scramble to wear every cardigan and light jacket before the Northeast's brief, beautiful autumn disappears.Springing Forward, On Purpose: Sarah explains how moving from sunny California to the Pacific Northwest flipped her feelings about daylight saving time.Peanuts, Umbrellas, and Baby Blue Jays: From a life-changing clear umbrella to a backyard full of peanut-hoarding birds, Sarah shares the small rituals that keep her feeling tuned in to the seasons.CHAPTERS:00:00 Josh's case for sweater weather02:31 Welcome, caller Sarah!05:00 Falling back, springing forward, and chasing daylight09:17 The umbrella that changed everything16:14 Baby blue jays and the peanut economy23:11 Good nightsSunday Edition: Dogs in Costumes w/ Fern Watt
26:31|Greta Johnsen talks with writer Fern Watt about the Tompkins Square Halloween Dog Parade and why dogs make the best icebreakers with strangers.What You'll Hear:A Parade Grown Too Big for the Park: Greta learns how a scrappy dog run tradition outgrew its space to become the 36th annual Tompkins Square Halloween Dog Parade.Gumshoe and the Odyssey: Fern walks through some of this year's most gloriously absurd costumes, proving New Yorkers will go to any lengths for their dogs.Named After a Dog, Apparently: Greta and Fern realize they both carry names more commonly found on a leash, and talk about what dogs teach us about loving, and losing, well.CHAPTERS:00:25 A zombie dress leads to an unexpected dog tangent01:24 Welcome, Fern Watt!03:41 Thousands of dogs, surprisingly calm chaos09:13 Pre-registration and an inbox full of inspiration21:31 Good nights!Costume Making is Her Passion
26:14|Greta Johnsen talks with Caller Nicole about Halloween costume-making for her daughter, from a papier-mâché submarine to this year's sparkly, spandex-heavy Boo.What You'll Hear:From Dolly Parton to Boo: Nicole walks Greta through her daughter's costume history, including a full Dolly Parton era complete with bedazzled boots and street performances.The Papier-Mâché Deep Dive: The two trade notes on wheat paste, balloons, and cardboard structures, proving that craft chaos is half the fun of Halloween.Two-Headed Freaks and Hobo Ghosts: Nicole and Greta swap stories of strange childhood costumes, from a Styrofoam head stuffed in a jacket to a very confusing hobo ghost.CHAPTERS:00:00 Halloween Week continues!01:20 The costume countdown02:45 Remembering Dolly Parton 05:39 Papier-mâché technique talk11:34 Dream family costumes, Totoro style21:24 Goodnights!Father-Daughter Halloween Costumes
21:40|Matt Bragg talks with caller Mike about father-daughter Halloween costume pairings, the economics of trick-or-treating candy, and the surprisingly spooky history of turnip jack-o'-lanterns.What You'll Hear:A Very Expensive Feather: Matt kicks things off with a frantic vet trip, a questionable hairball, and a bill steep enough to rival a nice dinner out.Eevee, Ash, and the Art of the Pairing: Mike shares how he and his seven-year-old daughter plan their matching Halloween costumes months in advance, from Wolverine and X-23 to a very cozy Pokémon duo.The Original, Unsettling Jack-o'-Lantern: Before pumpkins took over, people carved something far creepier, and Matt can't quite get over it.CHAPTERS:00:00 Matt's bloated black cat and Halloween chaos02:03 Welcome, caller Mike!03:17 Eevee, Ash, and family costume themes09:47 Planning months ahead for costume pairings15:53 Pumpkin carving memories and turnip jack-o'-lanterns18:14 Good nightsThe Ultimate Halloween Movie Marathon
28:26|Josh Gondelman talks with Caller Tim about his elaborate October movie marathon, from Witchy Wednesday to Sequel Saturday, and the campy gems most people have never heard of.What You'll Hear:A Calendar Built for Spooky Season: Tim explains the themed structure he's refined since the COVID days, complete with alliterative names like Macabre Monday and Fleshy Friday.The Deep Cuts Worth Digging Up: From a forgotten 1989 camp classic to the kitschy gimmicks of director William Castle, Tim shares the recommendations most of his friends had never heard of.When a Classic Doesn't Quite Fit: Josh and Tim debate whether beloved horror films like The Shining and Psycho belong in an October lineup at all.CHAPTERS:00:00 Josh's spotty horror movie education02:36 Welcome, Caller Tim!03:18 How Tim's October movie calendar began07:25 A tour through this year'd themes14:50 Underrated gems and campy favorites23:28 Goodnights!Her Wedding Dress, Zombified
28:51|Greta Johnsen talks with Caller Lauren about turning her wedding dress into a zombie bride costume and planning a Dracula-themed murder mystery for her husband's Halloween birthday.What You'll Hear:Zombie Bride and Groom, COVID Edition: Lauren tells Greta about the Halloween she and her new husband decided to reuse their wedding attire.Six Years, Two Daughters, One Dress: Looking back at those photos now, Lauren reflects on how much simpler Halloween costumes used to be before toddlers entered the picture.Dracula Turns 500: With her husband born on Halloween, Lauren shares plans for the ambitious murder mystery party she's throwing.CHAPTERS:00:00 Welcome to The Nightly01:15 Caller Lauren joins us!02:00 The zombie bride and groom plan05:00 Looking back six years later11:21 Planning a Dracula murder mystery18:25 Goodnight Lucy & Marcy!What Makes A True Halloween Wedding?
18:45|Matt Bragg talks with caller Alex about her Halloween wedding, two guests in hyper-realistic pigeon heads, and the great debate over what percentage dead is appropriately spooky.What You'll Hear:The 30% Dead Rule: Matt lays out his personal Halloween philosophy, which involves a strict minimum level of decomposition for any costume to count.An Aspen Tree Walks Down the Aisle: Alex describes her Halloween wedding's surprisingly elegant nature theme, plus the eight-foot talking jack-o'-lantern that now guards her front yard.Planning a Spooky First Anniversary: The two try to invent a Halloween-themed version of the traditional paper anniversary, with mixed results.CHAPTERS:00:00 Welcome back, caller Alex01:07 The Halloween wedding reveal03:18 The 30% dead costume rule05:00 Two guests in pigeon heads07:05 The eight-foot jack-o'-lantern from Target13:28 Planning a spooky anniversaryThe Neighborhood That Wins Halloween
27:14|Josh Gondelman talks with Caller Kathryn from Wichita, Kansas about her neighborhood's over-the-top Halloween traditions, from giant skeletons and fog machines to buses full of trick-or-treaters pouring in from out of town.What You'll Hear:A Childhood of Tinfoil and Felt: Josh remembers his mom's scrappy homemade costumes, from a cardboard robot to a Where's Waldo win that made him the talk of the block.Halloween Town, USA: Caller Kathryn describes her Wichita neighborhood's wild Halloween scene, complete with bussed-in trick-or-treaters, police blockades, and even a lost kids' station.The Great Candy Count: Kathryn breaks down exactly how many Costco bags it takes to survive an evening of nonstop doorbell rings, and why fun size is the only way to go.CHAPTERS:00:00 Josh's homemade Halloween costumes as a kid03:20 Welcome, caller Kathryn!04:07 A Hocus Pocus-level Halloween block party09:00 The candy situation14:40 A friend's legendary synchronized light show20:12 How to politely sit Halloween outSunday Edition: Bedazzling w/ Liberty Hardy
23:40|Greta Johnsen catches up with friend, book critic and crafter Liberty Hardy about the art of bedazzling.What You'll Hear:A Bedazzled Bucket Begins It All: Liberty traces her sparkly obsession back to a cracked drag-show confetti bucket that sat in her house for years before it sparked a whole new hobby.Eighteen Hours, One Neon Dog: Liberty walks through the surprisingly long, strangely meditative process of bedazzling a portrait of Greta's dog Buffy, gem by tiny gem.Permission to Have a Useless Hobby: At 50 years old, Liberty reflects on learning to relax, make things just for fun, and let herself waste time wisely.CHAPTERS:00:00 The inspiration for this week's Sunday Edition01:40 Say hello to bedazzler, Liberty!02:24 How a cracked confetti bucket started it all06:05 The 18-hour sparkle marathon16:16 Permission to have a useless hobby19:52 Goodnight, Buffy!