Hot Takes & Deep Dives

Jess is joined by fellow Long Islander ROSIE O'DONNELL! Topics: the inception of The Rosie O'Donnell Show, the infamous episode where Whitney Houston no-showed, her experiences with Britney Spears, being in the studio as Madonna recorded "This Used to Be My Playground" for A League of Their Own, why Barbara Walters disappointed her on The View, Kathy Griffin and Roseanne not taking her advice, The L Word, Queer as Folk and more! 

⭐ IG: @jessxnyc 

⭐ Jess' docu-series on the history, mystique & lore of Fire Island — Finding Fire Island

Jess is joined by Scissor Sisters frontwoman Ana Matronic (@msanamatronic)! Topics— first meeting JAKE SHEARS at The Slipper Room, STUART PRICE producing their "Night Work" album, the highs (and frustrations) of scoring a massive hit with "Let's Have a Kiki" while still failing to satisfy their record label, and why Ana chose not to reunite with the band on its current tour. Plus— Ana discusses losing her father to AIDS in 1990 and her work today as a Fire Island DJ and historian.

⭐ IG: @jessxnyc | @msanamatronic

⭐ Jess' docu-series FINDING FIRE ISLAND about the history, mystique and lore of Cherry Grove & The Pines.

Jess is joined by Ben Rimalower and Boy Toy Mike Fernandez to review Madonna's Confessions II! Topics: Sean Penn lore, could "Danceteria" have been the "Abracadabra" of the album, Ben & Mike's first listen midnight journey, each of our Top 3, songwriting camps & more! 

IG: @jessxnyc | @benrimalower | @mrmikefern

Jess' docu-series FINDING FIRE ISLAND about the history, mystique and lore of Cherry Grove & The Pines.

We will have our comprehensive review of CONFESSIONS II next week! But first, Jess joined by Mark Snyder & Kenny Finkle (All I Want To Do Is Talk About Madonna) and Tony Trius (MLVC) for a culture debate — MADONNA EDITION! Topics: our unpopular opinions, best live performance, best Truth or Dare moment, Tears of a Clown, how to fix Madonna, was longtime collab Mirwais trying to sabotage her? … and more!

IG: @jessxnyc | @tonytrius | @markbsnyder2026 | @mynameisfinkle

Jess' docu-series FINDING FIRE ISLAND about the history, mystique and lore of Cherry Grove & The Pines.

Jess is joined by David Kennerley to pour over his coffee-table book (Getting In) showcasing more than 200 flyers he collected from NYC queer bars & clubs of the 1990s (ie: Limelight, Splash, The Saint, Pyramid, The Roxy), with commentary from Michael Musto, Linda Simpson, Lady Bunny, Chip Duckett, Ernie Glam, Mark Allen and more! Topics: the "Disco Sucks" era, backrooms during the HIV/AIDS epidemic and more. 

⭐ IG: @jessxnyc | gettinginclubbook.com

⭐ Jess' docu-series on the history, mystique & lore of Fire Island — Finding Fire Island