My current guilty pleasure* is Whistlestop, a podcast about historical presidential elections.
I've always been fascinated by campaigns. Obviously I love history and (not so) obviously I love politics, but just learning about the personalities, the trends, the gaffes, the opportunities--it's all so interesting to learn what people like and hated and let sway their opinions. Saying phrases like "Rum, Romanism and Rebellion" or "Ma, Ma, Where's My Pa?" to an old history nerd like myself will get you the appropriate response in return**, so you can both talk about WIlliam Jennings Bryan in the corner while everyone else at the party is getting laid.
The podcast takes a single aspect of an election and tells the story behind it. Hosted by Slate magazine and narrated by the wry, amusing, and authoritatively John Dickerson of Face the Nation fame (so he's legit and all), they tend to be about a half hour where he delves into the details and the framework of an election.
Previous episodes include the infamous "Dean Scream," the inability of Mario Cuomo to jump in the race, Ed Muskie crying like a little girl, and Bill Clinton feeling your pain.
Even if you aren't a fan of either politics or history, I suggest listening to an episode or two. They are entertaining in and of themselves and aren't just dry bits of history chopped up for ease.
It does sadden me a bit to know that in anther generation or two, an episode of Whistlestop (or its functional equivalent) will be talking about the size of Donald Trump's penis. So goes the nation, and all that.
*Apparently, I don't know what "guilty pleasure" means. Listening to a historical podcast is rather enlightening, don't you think? It's not like I'm streaming Kim Kardashian Nudes on my phone. Well, not at this exact moment.
**"Gone to the White House, ha ha ha!"