2016 was terrible for a host of reasons. Prince died. Brexit happened. Independence Day without Will Smith. And that’s not even mentioning an election full of email servers, sexist comments and two amnesia filled moments for Gary Johnson. (Actually – those were pretty funny.) But, 2016 was truly a lost cause because of the one thing that none of us knew we were missing – the Crooked Media empire.
Like the rest of us, Jon Favreau, Jon Lovett and Tommy Vietor (and weekly guest host Dan Pfeiffer) spent 2016 obsessively following politics and trying to assuage the feeling that Donald Trump was consuming America faster than a man-eating virus. Except, while we were all sitting at bars and crying into our beers, they were hosting the Keepin’ it 1600 podcast for The Ringer. (In case you’re feeling nostalgic for a simpler time, The Ringer still has some of the shows available for streaming.) When the election news knocked us all down, the boys decided that now was the time to take their audience, and their charming sense of impropriety, in a new direction. Enter Crooked Media, which they describe as a “place to talk about politics the way actual human beings talk.” They started in January with one show, Pod Save America, and have since expanded to a roster of 5 shows producing 6 episodes a week.
So what makes this grouping so magical? A show built on the idea of three young white guys sitting in a room laughing at each others jokes doesn’t immediately spell success. Part of the appeal comes from the fact that, as their mission statement suggests, they talk more like your friends at a bar than the pundits on television. In a world full of confusion and political spin, everyone from the most obsessive to the most casual news consumer is looking for a forthright option. Most, if not all of us, are looking for smart people who can help make sense of a political climate that no longer seems to add up. Little did any of us think that we would find the straightforward solution in a group that proudly wears the mantle of being ‘crooked’.
Besides being educational, Crooked Media also brings an easy candor to conversations about hard topics. After 2016 many of us thought that we would never laugh again, but the company has unabashedly and successfully staked its claim at the intersection of scholastic and sarcastic. Pod Save America episodes include a run-down of the most salient news topics plus an interview with a leading politician, organizer, journalist or other noteworthy figure, which usually begin with the boys asking their guests the loaded and appropriate question ‘Since Donald Trump is president – how are you doing?’
This popularity paved the way for the corresponding show Pod Save the World, where Tommy Vietor showcases his foreign policy capabilities with today’s experts. Friend of the Pod (a status which we all covet) Ana Marie Cox now has her own show, With Friends like These, which discusses the different ways we can bridge divides, while activist DeRay Mckesson just launched Pod Save the People. This article would be remiss (and probably called out by the man himself) if it didn’t mention that Jon Lovett also has his own spin-off, Lovett or Leave It, which is a celebrity filled game show focused solely on the news. A strange combination that, as the title implies, either you’ll love, or you won’t.
In roughly five months, Crooked Media has grown from 3 guys with a dream (or, three and a half if you count Dan Pfeiffer) to a company with at least one of their podcasts consistently in the Apple Podcast App’s Top Ten List every week. (Specific streaming numbers are hard to come by, but they have almost 14,000 reviews on Pod Save America alone.) The question remains as to whether their blistering brand of information and irritation (mostly Jon Lovett) will continue to be relevant as the Trump autocracy (excuse me, so called democracy) continues to unfold. But, for right now, it’s enough that they are hitting a nerve (and a funny bone) in a way that the American people seem to desperately need.