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Did you know that hit songs in the late 1950s were regularly about gruesome death? Or that a US vice president wrote a number one hit? Chris Dalla Riva is one of my favorite music journalists out there. He writes the substack Can't Get Much Higher where he publishes pieces on the intersection of music and data.

A couple years ago he embarked on a quest to listen to every single number 2 hit from the last six decades, and wrote about what he learned in his new book Uncharted Territory. The book is part celebration, part takedown of popular music, and also provides new ways to think about your favorite songs, genres, and artists. This book is genuinely so good and changed the way I think about so many songs and just how different periods in history were reflected in the music from their time.

Chris joined me this week to discuss the past half a century of number 1 hits and what they say about our culture, political system and world at large.

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FREE SPEECH FRIDAY

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For the first time in fifteen years, there’s a real shot at ending billionaire control of American politics.

A groundbreaking legal effort spearheaded by Harvard law professor Lawrence Lessig, backed by an unlikely coalition of billionaires like Mark Cuban and Reid Hoffman, is taking direct aim at the legal foundation that created Super PACs.

I'm going to be covering this legal fight closely. Larry Lessig joined me on this week's Free Speech Friday to break down his legal fight, where things stand, and what needs to happen next in order to win this fight.

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Over the past two decades, Taylor Swift has dominated the pop charts and risen to the pinnacle of mainstream fame. She has amassed a $2 billion fortune, won 14 Grammy Awards, sold more than 100 million albums worldwide, headlined the highest-grossing concert tour in history, and built a vast real-estate and music catalog empire.

But lately, the backlash to Swift is growing louder. She has been criticized for her silence on major political issues, for palling around with Trump supporters, her carbon footprint, and many are calling her latest album a flop.

All of this raises the question, has Taylor Swift peaked, not just in popularity, but in cultural authority? Or is this just another cynical reinvention that she'll use to amass even more money and power? Journalist and Swiftie Kat Tenbarge joined me to discuss it all.

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