How to Train Your Dragon: Toothless Then & Now- Let Your Geek Sideshow Podcast

Susan and Kitty are spreading their wings and reaching new heights as they discuss the legacy of the How to Train Your Dragon franchise, the evolution of everyone’s favorite flying lizard Toothless, and more! Join us as we travel to the isle of Berk for How to Train Your Dragon: Toothless Then & Now.  This podcast is HTTYD: The Hidden World spoiler-free!


What happens when pop culture enthusiasts from different generations swap tales of their favorite modern and classic stories? Let Your Geek Sideshow presents… Then & Now– a pop culture podcast!


Press play above to listen along!

Who doesn’t love discussing dragons?  From humble beginnings as a children’s book series to capping an epic and beloved movie trilogy, Toothless and Hiccup have soared to new heights over the last decade. From books to movies and streaming cartoons, Toothless and the dragons of Berk have bonded not only with their riders, but our minds and hearts.

Are they misunderstood? Possibly, but aren’t we all? The ability to bridge the gap between what we think we know and what is true is what we ultimately take away from these stories.

Take a listen as we dive into the deep lore of Berk, Hiccup Horrendous Haddock III, Toothless the Night Fury (or Seadragonus Giganticus Maximus?), and more.


If you are interested in following the world of How to Train Your Dragon, check out the following sources:

  • How to Train Your Dragon (2010)
  • How to Train Your Dragon 2 (2014)
  • How to Train Your Dragon: The Hidden World (2019)
  • How to Train Your Dragon by Cressida Cowell
  • DreamWorks’ Dragons: Race to the Edge (Netflix)

You can check out the full Then & Now podcast on iTunes, or subscribe to our Youtube channel.  You can also find our channel hosted on Pippa at side.show/thennow.  Keep an eye out for new episodes and more ways to listen coming soon.  If you like the show, be sure to subscribe and leave a 5-star review so that other fans can find the podcast!

What other characters, films, or events would you like to see covered in upcoming episodes?  Let Your Geek Sideshow and tell us in the comments!


We are proud to bring you pop culture content completely AD FREE, but that doesn’t mean we don’t need your support to help keep us going. If you enjoy Then & Now, please take a moment to leave us a 5-star review on iTunes, Spotify, or your favorite podcasting platform and help spread the word about our podcast.

Be sure tune in for our other pop culture podcasts: Take a peek into geek culture and check out our Top 10 fandom favorites in the Geek Culture Countdown. Hear exclusive interviews with celebrities and pop culture industry leaders as they let their geek side show in Look Who Showed Up. Then, get all the latest pop culture news with our Daily Briefing, a two-minute breakdown of the biggest geek headlines perfect for your Alexa or Google news briefings.

We wouldn’t exist without your continued support. Thank you for listening, and don’t forget to Let Your Geek Sideshow!