Dive into the thrilling world of bobsledding as Conan chats with DeVaughn in Calgary. They share wild sledding tales, including hilarious workout routines and the chaos of crashes. Enjoy whimsical winter adventures and the joys of hosting on Airbnb, plus playful banter about beer and Valentine's Day shopping. The conversation also touches on the challenges of funding Olympic sports and the cleverness needed for personal branding. Lastly, reminisce about childhood memories and the excitement of unexpected encounters in comedy.

Kaitlin Olson, celebrated for her role as Dee Reynolds in 'It's Always Sunny in Philadelphia,' joins the conversation to share her quirky experiences. She dives into her new ABC crime series 'High Potential,' cooking with husband Rob McElhenney, and the hilarious challenge of introducing their kids to the show's unique humor. There’s also a fun quiz on trucker lingo that showcases the absurdity of CB slang, blending nostalgia with humor. Expect laughter and candid moments as she and Conan navigate the ups and downs of her career and family life.

A lively conversation unfolds as guests dive into the lighter side of medical training, sharing laughs about colonoscopies and fasting for eight days. The chaotic dynamics of proposing to a partner with jeweler parents spark humorous exchanges about engagement ring negotiations. They tackle food cravings after fasting and explore the intersection of modern medicine and cultural practices. The camaraderie among friends shines through in comical discussions about proposal traditions, blending heartfelt moments with laughter.

Ben Stiller, the renowned actor and filmmaker behind hits like Tropic Thunder and the series Severance, returns for a candid chat with Conan. They delve into the hilarious process of convincing Tom Cruise to join Tropic Thunder and the journey of documenting his parents' comedic legacy. Stiller shares thoughts on the anticipated second season of Severance and reflects on the creative challenges faced during the pandemic. Amidst laughter, they connect over the absurdities of fandom and an amusing burglary involving Conan's merch. It's a delightful ride through comedy and creativity!

Civil War historian Cooper Wingert shares his passion for history with wit and humor. He and Conan explore whimsical ideas, like how to integrate Civil War chatter into a first date. They ponder Conan's battlefield skills while laughing about creative reenactment strategies. The duo also delves into captivating ways to engage younger audiences with history, by mixing pop culture into educational tours. Their playful banter reveals the charm of embracing unique interests, making history both entertaining and accessible.

Three hosts share their emotional journeys following devastating wildfires, highlighting personal losses and the resilience of their community. They discuss the absurdity of grieving possessions while finding moments of humor amidst the chaos. The importance of supporting vulnerable populations is emphasized, along with the challenges of navigating technology and family dynamics. Ultimately, they express gratitude for support systems that emerge during crises, shedding light on the power of connection, hope, and recovery.

Donovan, a minor league professional wrestler known for his Conan O'Brien-inspired persona, Danhausen, discusses the amusing and creative sides of wrestling. He dives into the evolution of characters in the sport and how humor captivates audiences. The conversation also touches on family dynamics and the influence of mothers on their comedic journeys. Banter about mental health and Canadian culture adds a relatable flair, while a witty exchange about guitar playing and unexpected legal threats wraps up the lively discussion.

In this entertaining chat, Jeff Goldblum, the iconic actor known for his roles in Jurassic Park and Independence Day, shares his whimsical dreams and explores the emotional connection of music and friendship. He and Conan discuss memorable movie moments, the joys of Airbnb travel, and the significance of classic films in their lives. Goldblum opens up about reprising Dr. Ian Malcolm in Jurassic World: Dominion, while their playful banter showcases Goldblum's unique charm and improvisational brilliance.

In this engaging discussion, relationship expert John Gottman, co-founder of The Gottman Institute, shares fascinating insights into marriage stability and conflict resolution. He humorously explores the dynamics of relationships, using an iceberg analogy for life's challenges. The conversation also dives into the importance of effective communication, highlighting how humor can strengthen connections. Gottman provides practical tips for navigating grievances, emphasizing empathy and understanding in partnerships. Tune in for laughs and valuable relationship wisdom!

Conan chats with Eugenia Fernandez de los Ronderos Jiménez, a physician resident in Madrid, who shares her experiences of cross-cultural love with her Irish-American fiancé. They discuss the quirks of public displays of affection and how cultural differences shape their relationship. Eugenia brings humor to the challenges of navigating intimacy and societal norms. The conversation also veers into entertaining travel stories and wedding chaos, providing a light-hearted examination of romance and the complexities of connecting across cultures.