Madame X was Madonna’s return to angry political messaging, not unlike American Life. But the 2019 release’s embrace of Portuguese, Brazilian, and Latin music influences distinguishes it as a unique sonic landscape for the artist, as Tristan and author, screenwriter, and producer Abdi Nazemian discuss.

Rebel Heart is probably the purest example of the trend the past few episodes of the show have addressed: that of Madonna’s, shall we say, extensive array of producing and songwriting collaborators. While Tristan and friend of the show JT_Lizzard differ somewhat on how successfully that comes out in the wash, the maligned 2015 release still has some distinct pleasures.

MDNA, released in 2012, defines Madonna’s approach to production collaboration in the 2010s; that is to say, with a wide array of songwriting “camp” teams. Tristan and Michael Dango, Associate Professor of English at Rice University and author of Madonna’s Erotica (an installment of the 33 ⅓ series), discuss the heights born out of this diffused working style as well as the questionable moments of the album.

Released in 2008, Hard Candy noticeably carries the production and songwriting tendencies of its all-star collaborators. Music writer Sydney Urbanek and Tristan discuss the good and bad of those tendencies and how Madonna’s own presence is integrated, or subsumed, in an unprecedented way.

For quite a few, Confessions on a Dance Floor, released in 2005, is Madonna’s “last great album.” While that may not exactly be the conclusion Tristan and film historian and cultural critic PT Klein come to, they certainly find its distillation of music that makes you move and sweat exhilarating.

Not since Erotica had Madonna faced as much controversy as she did with American Life. Her artistic statement on the state of the country and world, released in 2003 in the midst of the “Bush II era,” is often intentionally abrasive but has many fascinating and enjoyable facets, as Tristan and Giulio Mazzoleni, author of Madonna Songbook and host of the podcast of the same name, explore.

Released in 2000, Madonna’s Music ushered in the 21st century for the everlastingly iconic pop star. And it did so with still-impressive forethought and freshness, which Tristan and friend of the show Trevor Bermingham constantly appreciate even for all its nostalgic qualities.

Ray of Light is often cited as Madonna’s greatest album. That’s a heavy expectation, but as basically Madonna novices Tristan and Caitlin Casiello, Assistant Professor of Japanese Film and Media Studies at the University of Florida, discuss, it’s one that the 1998 release could understandably live up to.

Evita was a major push for Madonna’s film career as well as her musical artistry, notably stretching her voice to new ranges to accommodate the Andrew Lloyd Webber sound. Tristan and theater artist and writer Ben Gierhart discuss the expansiveness, the messiness, and the moments of brilliance to come from the 1996 release, Madonna’s final soundtrack album to date.

Discussion about Bedtime Stories, released in 1994 and two years after Erotica, is defined by the conscious “softening” of Madonna’s image. And as Tristan and former film critic and podcaster Michael Snydel address, that shift, especially in her embrace of contemporary R&B sounds, isn’t always successful, even as the record has a bit more edge than its been given credit for.