I started listening to podcasts when podcasts first became podcasts.
Way back in 2005, as Elysha and I were moving from an apartment on one side of the street to an apartment on the other, I was listening to podcasts. In the beginning, I was listening primarily to This American Life and tech podcasts (which were popular and plentiful back then, given that listening audiences required a background in technology in order to download episodes onto MP3 players and pre-iPhone cellular phones).
After listening to tens of thousands of hours of podcasts, it's impossible to choose a single best episode of all time, but this episode of the very excellent podcast Heavyweight is one of my favorites of all time.
I cannot recommend it highly enough.
If you're wondering what Heavyweight is about, it's hard to say. From Gimlet Media's website:
Maybe you’ve laid awake imagining how it could have been, how it might yet be, but the moment to act was never right. Well, the moment is here and the podcast making it happen is Heavyweight. Join Jonathan Goldstein for road trips, thorny reunions, and difficult conversations as he backpedals his way into the past like a therapist with a time machine.