Actor, producer, writer, and Robot Chicken co-creator Seth Green digs into David Bowie’s landmark 1971 album Hunky Dory, exploring Bowie’s transformation into a global icon, the brilliance behind songs like “Changes” and “Life on Mars?,” and how the record’s fearless creativity still resonates today.

Drew Carey does a deep dive into Aftermath, the electrifying album that launched The Rolling Stones into a bold new era of fully original songwriting.

When comedian Holly Anabel Brown was 17, her dad was dying of cancer when he dropped a bombshell: she had twin brothers she never knew existed - young boys her entire extended family had kept secret. After his death left her with more questions than answers, Holly sets out to uncover how a secret this big could be hidden, and why the sitcoms that raised her were often the only way to make sense of a life stranger than TV.

Roddy Bottum of Faith No More unpacks the raw charm and lasting influence of Loaded, the record that turned The Velvet Underground’s downtown art-rock spirit into something generations of outsiders could sing along to.

Josh sits down with his ex-girlfriend Brittany Furlan for a funny and unexpectedly personal conversation about love, history, and why The Bends remains one of Radiohead’s most emotionally resonant records.

Comedian Beth Stelling breaks down The Mamas and the Papas’ 1966 debut, If You Can Believe Your Eyes and Ears, exploring how its sun-soaked harmonies and era-defining hits like “California Dreamin’” captured a cultural moment and helped shape the sound of a generation.

What happens when one of rock’s greatest drummers dives into one of its most influential albums? Stewart Copeland joins The 500 With Josh Adam Meyers to unpack Cream’s Disraeli Gears, from its psychedelic breakthroughs to the riffs that changed rock forever.

Josh sits down with Dethklok creator Brendon Small to explore The Who Sell Out by The Who, diving into the album’s pirate radio concept, Pete Townshend’s early rock opera ambitions, Keith Moon’s explosive drumming, and how satire, storytelling, and theatrical rock helped shape the future of heavy music and concept albums.

Wayne Federman returns to dive into The Rolling Stones’ breakthrough album Out of Our Heads, exploring its blues roots, the creation of “Satisfaction,” and how it helped define rebellion, identity, and the sound of rock music in the 1960s.

Cody Tucker joins the show to unpack the album where Eric Clapton essentially wrote a 77-minute diary entry about desperately wanting his best friend's wife, and somehow it became one of the greatest rock records ever made.

Comedian Sam Jay joins the show for a deep and unfiltered conversation about Kanye West’s Late Registration, breaking down its orchestral ambition, political fire, vulnerable family moments, and the cultural forces that made it one of hip-hop’s most pivotal sophomore albums.

Comedian Wayne Federman joins the show to explore At Last!, unpacking Etta James’ life, voice, and cultural impact, and how this timeless album bridged blues, soul, pop, and emotional truth in American music history.

Comedian and cultural obsessive Wayne Federman returns to The 500 to dig into Sweetheart of the Rodeo by The Byrds, unpacking how a rock band’s leap into country music reshaped American songwriting, sparked controversy, and quietly changed the future of popular music.

Loni Love returns for her fifth appearance on the podcast to discuss the groundbreaking album that showed pop music could embody both celebration and protest, Sly and the Family Stone's Stand!

Jackie Fabulous joins the podcast for the first time to discuss the The Harder They Come Motion Picture Soundtrack, the record that brought reggae to the world, and to decide if Jimmy Cliff belongs on the Mount Rushmore of reggae.

Erik joins the podcast for the second time to discuss one of the most influential records in hip-hop history that redefined Run D.M.C.’s career and cemented hip hops place in pop culture.

Over time, this album has been considered one of the great lost masterpieces that wasn’t appreciated in its time. Wayne Federman makes his 25th appearance to break it down.

Greg Fitzsimmons makes his third appearance to discuss one of the iconic voices and artists of the 1960s.

Ian Edwards makes his third appearance on the podcast to discuss the album that pushed The Wailers to global status.

Craig Shoemaker makes his debut on the podcast to discuss The Byrds album that features “So You Want to Be a Rock ’n’ Roll Star”.

Maria Bamford makes her debut on The 500 to discuss the album that was a turning point for Iggy and The Stooges

Greg Proops makes his return to The 500 to discuss the most influential album from the Talking Heads' catalog.

Wil Wheaton makes his debut on The 500 to discuss Television’s debut album that bridged the gap from New York Punk to the post-punk and indie guitar sound

Jim Norton joins Josh & some special guests offer their thoughts to discuss the landmark Black Sabbath sophomore release