While I love listening to music on road trips, I do get bored listening to Mike Will Made It songs (see: every song on the radio) for 5+ hours. To combat this, I throw on some podcasts. If you aren't familiar with podcasts, you're probably thinking of this or this. OK, so you wouldn't be entirely wrong. Fortunately, there are tons of decent podcasts out there. Here are the ones I like to listen to during long drives, train rides, and flights.
I like to think of Radiolab as like This American Life + science. Hosts Jad Abumrad and Robert Krulwich focus on science and philosophy themes (like time and morality) in an accessible and (sometimes) light-hearted way. Jad fancies himself a sound designer and soundscapes the episodes -- sometimes it works and sometimes it doesn't (in my opinion).
This podcast, produced by Slate, is a clever and funny take on linguistics. Host Bob Garfield and producer Mike Vuolo talk about language, from pet peeves, syntax, and etymology to neurolinguistics and the death of languages. The last one that I listened to was a little while back called "Learning to Say No" (how we learn from a young age to master negation) and it was fantastic.
At this point most people are familiar with Ira Glass and his storytelling podcast (hell, it was even a series on Showtime a few years back), but its still a solid listening choice. Each week's show has a theme, which is explored in several "acts." Though content varies widely by episode, most stories are first-person narratives.
This podcast about economics is actually produced by the TAL guys, so you know its worth listening to. Here's how they describe the podcast: "Imagine you could call up a friend and say, 'Meet me at the bar and tell me what's going on with the economy.' Now imagine that's actually a fun evening. That's what we're going for at Planet Money." That's a pretty accurate description. I haven't listened to this podcast too much, but my favorite of the ones I've heard is the episode about setting up an offshore shell company. It's hilarious, informative and frankly, a little frightening.