How We Made Your Mother

In this episode of How We Made Your Mother, Josh, Craig, and Alek dive into Season 2’s “Columns,” which explores the unexpected loneliness of becoming the boss. The conversation centers on Ted Mosby’s role reversal with Hammond Druthers (played memorably by Bryan Cranston), drawing directly from Craig and Carter Bays’ real experiences suddenly becoming showrunners with no training and realizing that success can be isolating. The hosts reflect on gossip, power, firing people, and the strange emotional distance that comes with authority, while also celebrating writer Matt Kuhn’s first-ever TV script and his journey from writers’ assistant to successful showrunner—an example of raising your hand, doing the unglamorous work, and being noticed. Along the way, they unpack the episode’s old-school A/B story structure, the nude Marshall painting subplot, classic jokes (new d’art, Margarita Fridays), and behind-the-scenes memories, before closing with heartfelt listener letters that underscore how How I Met Your Mother continues to soundtrack people’s real lives in nonlinear, meaningful ways.

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This week’s episode is a big, warm, lore-heavy love letter to one of How I Met Your Mother’s most meaningful episodes. Josh and Craig talk about why “First Time in New York” works so well: filling in backstories, sneaking past network standards with euphemisms, and still making real present-day moves like Robin finally saying “I love you.” They dig into the Dirty Dancing sequence (yes, it cost a lot), Lucy Hale’s early guest spot, Barney’s secretly heartbreaking virginity story, Marshall and Lily’s lobby-vs-top-of-the-building debate, and Ted’s eternal romance with the Empire State Building. Along the way, they get reflective about how we edit our own memories, why stories matter, and how HIMYM has become a comfort show for people all over the world—ending with emotional listener letters, New York recommendations, and a reminder that people will, in fact, dance.

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Josh Radnor and Craig Thomas revisit Season 2, Episode 11, “How Lily Stole Christmas,” the show’s first real Christmas episode—and one of its most emotionally honest. They talk about the fallout from Marshall and Lily’s breakup, especially Ted’s complicated position as best friend to both of them, and how the episode hinges on a single censored insult (the infamous “Grinch”) caught on an answering machine—an extremely 2006 plot device. The conversation digs into what a best friend actually owes you after a breakup, why Ted’s anger at Lily is about more than just defending Marshall, and how that confrontation ends up being about friendship, hurt feelings, and chosen family. Along the way they shout out Barney’s sickness subplot, Christmas movie influences like A Christmas Story and Love Actually, and reflect on why this episode still hits hard for fans who return to it every holiday season as a comfort watch.

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Official Website (Send us your audio and written messages)

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READ JOSH’S MUSELETTERS ON SUBSTACK:

Subscribe HERE.

CRAIG’S BOOK IS AVAILABLE!

Head over to CRAIG’S WEBSITE to order your copy of THAT’S NOT HOW IT HAPPENED.

SUPPORT PEDIATRIC CONGENITAL HEART DISEASE RESEARCH:

Click HERE to learn more and donate today.

FOLLOW THE OFFICE LADIES:

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AND MORE:

Josh’s Official Website

Josh on Spotify

Craig’s Official Website (with links to his published writing)

Alek’s “Dead Fathers Society” on Substack


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In this episode of How We Made Your Mother, Josh and Craig welcome the brilliant Wayne Brady to revisit “Single Stamina,” the Season 2 episode that introduced Barney’s gay, Black brother James. Together they unpack how Wayne came to the show, what it felt like to embody this new character, and how the episode balanced outrageous comedy with genuine heart. They discuss James as both brother and father figure to Barney, the themes of aging, vulnerability, and growth that define the show, and how the episode’s subtle pro–gay-marriage message felt quietly radical in 2006. Wayne shares memories of working with Neil Patrick Harris, his nerves walking onto set, and how he approaches comedy and fear as a performer. Josh and Craig reflect on the episode’s legacy, its GLAAD Media Award nomination, and how it captured HIMYM’s mix of humor, heart, and social progressiveness.

CONNECT WITH THE SHOW:

Official Website (Send us your audio and written messages)

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READ JOSH’S MUSELETTERS ON SUBSTACK:

Subscribe HERE.

CRAIG’S BOOK IS AVAILABLE!

Head over to CRAIG’S WEBSITE to order your copy of THAT’S NOT HOW IT HAPPENED.

SUPPORT PEDIATRIC CONGENITAL HEART DISEASE RESEARCH:

Click HERE to learn more and donate today.

FOLLOW THE OFFICE LADIES:

Check out "Office Ladies" at https://officeladies.com/ or wherever you get your podcasts!

Follow on Instagram: OfficeLadiesPod

Follow on TikTok

AND MORE:

Josh’s Official Website

Josh on Spotify

Craig’s Official Website (with links to his published writing)

Alek’s “Dead Fathers Society” on Substack


To learn more about listener data and our privacy practices visit: https://www.audacyinc.com/privacy-policy

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To celebrate New Years, we are flashing back to our Season 1 rewatch of “The Limo.” Josh and Craig recall the episode’s ambition to be a “simple shoot” that turned out to be one of the most technically challenging due to the cramped limo set, and share behind-the-scenes stories like Jason Segel’s triumphant foggy entrance, the difficulty of getting camera shots in the limo, and the running joke of “the circuits are jammed.” They marvel at the Emmy-winning cinematography, the comic perfection of Bon Jovi’s “You Give Love a Bad Name,” and how the episode balances magical realism with emotional honesty. Josh highlights the cinematic final shot and the episode’s theme—that life’s unexpected detours are all part of the journey. They praise guest stars like Kathleen Perkins (Mary Beth) and JP Manoux (Not Moby), reflect on their own formative pop culture experiences, and read fan letters, including one from a Canadian listener whose wedding was filled with HIMYM references. Jordana, Josh’s wife and a clinical psychologist, closes with an insightful commentary on the spiritual lesson embedded in Ted’s narration: not everything has a happy ending, but it’s all important.

CONNECT WITH THE SHOW:

Official Website (Send us your audio and written messages)

Instagram

READ JOSH’S MUSELETTERS ON SUBSTACK:

Subscribe HERE.

CRAIG’S BOOK IS AVAILABLE!

Head over to CRAIG’S WEBSITE to order your copy of THAT’S NOT HOW IT HAPPENED.

SUPPORT PEDIATRIC CONGENITAL HEART DISEASE RESEARCH:

Click HERE to learn more and donate today.

FOLLOW THE OFFICE LADIES:

Check out "Office Ladies" at https://officeladies.com/ or wherever you get your podcasts!

Follow on Instagram: OfficeLadiesPod

Follow on TikTok

AND MORE:

Josh’s Official Website

Josh on Spotify

Craig’s Official Website (with links to his published writing)

Alek’s “Dead Fathers Society” on Substack


To learn more about listener data and our privacy practices visit: https://www.audacyinc.com/privacy-policy

Learn more about your ad choices. Visit https://podcastchoices.com/adchoices