Greatest Pop Stars of the 21st Century Podcast: Miley Cyrus (No. 15) & Justin Timberlake (No. 14)

On this week’s (Sept. 6) episode of the Greatest Pop Stars of the 21st Century podcast, we take a look at a pair of Tennessee natives: Fictional pop superstar turned IRL pop superstar Miley Cyrus (No. 15) and *NSYNC spotlight-stealer-turned-solo game-changer Justin Timberlake (No. 14).

First, host Andrew Unterberger is joined by Billboard Social Media Manager Danielle Pascual and Billboard Pride Editor Stephen Daw to talk about Miley Cyrus’ one-of-a-kind career path from Hannah Montana to “Flowers.” We discuss why the Billboard staff (and its Zillennials in particular) seems to have a particular rooting interest in Cyrus’ career, revisit the highs and lows of the unforgettable Bangerz era, and defend some personal favorites from her long journey back to the top of the charts. We also introduce a new category to our closing lightning round of questions to be able to properly ask: Are we sure “Flowers” was really that good?

Then, we welcome back a pair of returning GPS podcast guests in Billboard Executive Director of Music Jason Lipshutz and R&B/Hip-Hop Chart Manager Trevor Anderson to talk about the two uneven halves of Justin Timberlake’s 21st century-spanning career: 15 years of near-uninterrupted ascendance, followed by a last decade that’s seen him take a bit of a tumble. We share memories from the late days of *NSYNC and early days of his solo breakout, zoom in on what made him the top pop star in the entire game for at least one album cycle, and explain why his 20/20 Experience era was both the absolute peak for his career and a foreshadowing of his decade to follow. And of course, we offer Super Bowl memories — from both 2004 and 2018 — and ask what, if anything, JT can do to turn around his career momentum in present day.

Listen to our latest below, catch up on our past episodes here, and be sure to subscribe to Billboard‘s Greatest Pop Stars of the 21st Century series wherever you get your podcasts! (New episodes will be revealed every Friday, following the publishing of our two new Greatest Pop Star rankings for that week.)