rob recently asked for musical recommendations for his lengthy roadtrip to Colorado. Offering musical opinions is one of my core competencies here. And postcount is huge. So here are some suggestions.
Starting in-house, you should check out We Defy Augury, especially the one about Charismatic Megafauna because you probably never think about these beasts. Also, Les Coole and the Cukes, available here on Spotify. I celebrate their entire catalog. And our resident professional musician, Rootstone.
We also have recurring bits of derivative in-house content including Whitney's 6-pack, zshazams, layzman's filler, and top 10.
Sometimes I let someone else do the driving musically when I'm driving automotively--I let the folks on the radio pick the music for me. I've touted WFMU here many times, and you can stream it from your phone to your car. In fact they have four different streams at all times: their radio live stream, Rock 'n Soul Radio, Give the Drummer Radio, and Sheena's Jungle Room. And they have an insanely deep archive. Rex Doane's Fool's Paradise is my personal favorite and he has over twenty years of shows available to stream. The Halloween and Christmas specials are always outstanding. You can also stream WBGO--Felix Hernandez's Rhythm Review on Saturday and Sunday mornings is my favorite. They have archives too but the interface is clumsy. I've found myself listening to WFUV during the day lately and you can stream them too.
Those three stations will take care of you. To w(h)it, whilst running a few errands yesterday and flipping between FMU and BGO (FUV is useless on Sundays, they play Irish folk music), I heard "Revolution Rock" by the Clash, "Me and My Baby Brother" (on BGO) and "Summer" (on FMU) by War, "Too Busy Thinking About My Baby" by Marvin Gaye, "Never Can Say Goodbye" as done by Gloria Gaynor, "Brick House" by the Commodores, "If I Were Your Woman" by Gladys Knight and The Pips, "Master Blaster" by Stevie Wonder, and "You Outta Be Here With Me" by Annette Snell. I even heard "Don't Cha Wanna Ride" by Joss Stone and the song that it samples, "Soulful Strut" by Young-Holt Unlimited.
I don't listen to a ton of podcasts but I greatly enjoy The Bulwark's offerings. Charlie Sykes is always good. Here's one with Chris Krebs and Adam Kinzinger. Anything involving Tim Miller is fun, like this one with the Tribe's own Jen Psaki. Mona Charen will irritate you but I do think it's good to hear opinions that conflict with my own. Will Saletan's "The Corruption of Lindsey Graham" is a three-part tour de force.
Anyone with other/better ideas should list them in the comments. I eagerly await photographic reports from rob along the way.

