Anjelah Johnson-Reyes celebrates Buddy Holly’s 20 Golden Greats, exploring the timeless songs, unmistakable sound, and enduring influence of one of rock and roll’s most groundbreaking pioneers.

Finesse Mitchell joins Josh to explore Prince’s genre-defying masterpiece Sign “” the Times, unpacking the music, artistry, and enduring brilliance behind one of the Purple One’s most celebrated albums.

Actor and musician Lukas Haas to explore the timeless heartbreak, honky-tonk spirit, and enduring influence of country music legend Hank Williams through his essential collection 40 Greatest Hits.

Comedian James Mattern is back to dive into Miles Davis’ groundbreaking Bitches Brew, exploring the album’s fearless fusion of jazz, rock, and experimentation as well as the lasting impact of a record that changed the course of modern music.

Comedian Jeff Arcuri joins for a hilarious and insightful deep dive into The Who's groundbreaking rock opera Tommy, exploring its lasting impact on rock music, storytelling, and pop culture.

Join Josh and comedy legend Lewis Black as they dive into Bob Dylan's The Freewheelin' Bob Dylan, exploring the groundbreaking songwriting, cultural impact, and timeless protest anthems that helped redefine American music and launched one of history's most influential artists.

Josh is joined by the Sklar Brothers to dive into Elvis Costello's explosive 1978 classic This Year's Model, exploring its razor-sharp songwriting, punk energy, and the album's lasting influence on rock music.

Legendary comedian Luenell drops in to explore There's a Riot Goin' On, the groundbreaking album's raw emotion, revolutionary sound, and lasting influence on funk, soul, and popular music.

Comedian, actor, and comedy historian Wayne Federman is back for a deep dive into The Zombies' timeless 1968 masterpiece Odessey and Oracle.

Actor Steve Schirripa explores Frank Sinatra's landmark 1955 album In the Wee Small Hours, discussing its timeless songs, groundbreaking concept, and enduring influence on popular music.

Comedian Wayne Federman returns to dive into Cream’s groundbreaking debut album Fresh Cream.

Comedian James Mattern to explore the brilliance and lasting influence of John Coltrane's groundbreaking 1960 masterpiece, Giant Steps.

Grammy-winning singer-songwriter Jason Mraz explores the timeless songs, deeply personal storytelling, and enduring legacy of James Taylor's landmark 1970 masterpiece, Sweet Baby James.

Actor, comedian, writer, and director Ken Marino explores Ray Charles' groundbreaking 1962 classic Modern Sounds in Country and Western Music, unpacking how the legendary artist transformed country music, shattered genre boundaries, and created one of the most influential albums in American music history.

Anthrax drummer Charlie Benante blasts into the Ramones’ 1977 punk landmark Rocket to Russia, exploring the album’s lasting influence on punk, thrash, and the sound of rebellious rock and roll.

Aisha Tyler celebrates Sam Cooke’s Portrait of a Legend 1951–1964, exploring the timeless voice, groundbreaking soul legacy, and unforgettable songs that changed popular music forever.