Former Obama speechwriter, comedian, and co-founder of Crooked Media Jon Lovett is making one of the biggest changes to his podcast’s history, and he’s doing it with all the Hollywood desire he can muster. If you like progressive podcasts, Lovett or Leave It has been a fan favorite for years. Now, the show is starting a new episode that is bigger, faster, and definitely more movie-like.
From the Hollywood Improv to Interwoven Studios
The show originally started as a live comedy quiz show recorded at the Hollywood Improv and released as a podcast. Over the course of 500 episodes, it evolved and grew as Crooked Media built an impressive audience and community, home to conversations you simply can’t find anywhere else.
Now, that era is giving way to something far more ambitious. Starting on April 30th, Lovett or Leave It is recording in front of a live audience on a stage at Interwoven Studios Hollywood, and the show is expanding — beginning with two episodes each week, recording live on Tuesdays and Thursdays. The monologues will air immediately on YouTube on Tuesday and Thursday nights, with full episodes posting on Wednesday and Thursday mornings wherever podcasts are available.
This is not a minor venue upgrade. It’s a fundamental reimagining of what the show can be.
Why the Move? Too Much News, Not Enough Episodes
The reasoning behind the expansion is refreshingly straightforward. There is simply too much news to cover in one weekly episode. The move to a brand new studio gives the show the ability to produce more episodes and turn those episodes around much faster. The new stage setting also gives the show the ability to reimagine its production for viewers at home, while keeping the weird, wild energy of America’s best live audience.
In an age when political news cycles churn relentlessly, a once-a-week comedy recap simply doesn’t cut it anymore. Lovett’s decision to double the cadence reflects a genuine responsiveness to the media moment — and to his deeply engaged audience.
The Show: Comedy Meets Politics at Its Sharpest
For the uninitiated, Lovett or Leave It is a one-of-a-kind format. Former Obama speechwriter, self-described comedian, and Pod Save America co-host Jon Lovett takes the stage for a show that has dared guests from Danny DeVito to Amy Klobuchar to ask “What is this?” and “Where am I?” Each week, Jon breaks down the biggest and dumbest stories in politics with big guests and surprising conversations you won’t find anywhere else.
The show is proudly the only place where you’ll find drag queens and senators equally confused as to where they are.
The show has popular recurring segments like “The Rant Wheel,” where Lovett picks a topic at random from a list or an idea from the audience; “Too Stupid to Be True,” where an audience member tries to guess whether quotes given by the panel are real or fake; and “Gay News,” where Lovett and a guest read news stories and jokes about LGBTQ celebrities and culture.
A Guest List That Spans All of Hollywood and Washington
What really separates Lovett or Leave is what makes it unique is the wide range of people it brings together on stage. Comedians Sarah Silverman, Brett Gelman, Ira Madison III, and Paul Scheer, author Wil Wheaton, and reporters Lauren Duca, Ronan Farrow, and Katie Nolan have all been on the panel. Recently, comedians Brett Gelman and Rheeqrheeq Chainey, Guy Branum, and Aida Osman have been speakers.
The breadth of that roster — politicians, comedians, journalists, actors — is exactly what the new Hollywood studio format is designed to amplify.
Crooked Media’s Growing Empire
Lovett or Leave It doesn’t exist in isolation. It’s part of an increasingly powerful media operation. Crooked Media, launched in 2017 by former Obama administration staffers Jon Lovett, Jon Favreau, and Tommy Vietor, has become a destination for progressives as podcasts exploded as a top platform in the political space.
That influence has caught the attention of major television networks too. In a notable video podcast pact, highlights from Crooked shows such as Pod Save America and Lovett or Leave It now air on MS NOW Saturdays at 9 p.m. ET, as video podcasts gain in popularity and take up a greater share of the media landscape.
Who Is Jon Lovett?
America’s Jonathan Ira Lovett is a podcaster, comedian, reporter, and former copywriter. He helped start Crooked Media with Jon Favreau and Tommy Vietor. The three of them worked together in the Obama White House during the political campaign. In addition to podcasting, he co-created the NBC sitcom 1600 Penn and wrote for HBO’s The Newsroom during his move from the West Wing to Hollywood. These roles showed off his versatility and sharp comedic voice, which continues to shape political commentary for millions of viewers.
How to Watch or Attend
If you’re in LA, you can attend a live taping at the new home at Interwoven Studios Hollywood, be part of the studio audience, and see what gets cut from the show — and what doesn’t. For everyone else, the show is available on YouTube and wherever you listen to podcasts.
