What Made Madonna’s 1995 Such a Fascinating Transition Year in Her Pop Stardom?

As 1995 began, Madonna was still an A-plus-list superstar and one of the most famous people in the world — but she was no longer at the absolute center of pop music. A half decade of increasingly controversial (though often brilliant) albums, singles, videos, movies and appearances had left the public divided and unsure about the Queen of Pop’s standing, while the dance-pop she’d conquered the world with in the ’80s had fallen out of fashion in a top 40 landscape dominated by alt-rock, hip-hop and R&B. But ’95 saw her reclaim her radio supremacy, while still taking huge artistic chances and pivoting to a more mature cross-platform star persona — though hardly all at the same time.

In this week’s Vintage Pop Stardom episode of the Greatest Pop Stars podcast, host Andrew Unterberger is joined by Keith Caulfield, Billboard‘s Managing Director of Charts & Data Operations (and co-host of the Billboard Pop Shop Podcast, and longtime M disciple) to express ourselves and not repress ourselves about Madonna’s incredibly fascinating 1995. We pick up mid-Bedtime Stories rollout with Madonna, as she improbably scores the biggest Billboard Hot 100 hit of her entire storied career, and we make it through her LP’s experimental final two singles (and their rather notable music videos), through getting cast in the film role of a lifetime, through the ’95 Video Music Awards, and finally end with her Something to Remember era, while she preps the world for a year of Oscar campaigning.

In the meantime, we brace the most important questions about La M as she reached the midpoint of her 1990s: Which super-cool-and-acclaimed European act made for better Madonna collaborators, Björk or Massive Attack? Why does nobody remember that “Take a Bow” was her longest-running No. 1? Should “Human Nature” have been a bigger hit? Was Evita worth shutting down her mid-’90s touring plans for? Did she really deserve a Razzie for her Four Rooms appearance? And of course: How did she fare in her infamous interview showdown with Courtney Love following the ’95 VMAs?

Check it out above — along with a YouTube playlist of some of the most important moments from Madonna’s 1995, all of which are discussed in the podcast — and subscribe to the Greatest Pop Stars podcast on Apple Music or Spotify (or wherever you get your podcasts) for weekly discussions every Thursday about all things related to pop stardom!

And if you have the time and money to spare, please consider donating to any of these causes in the fight for trans rights. (Madonna would want you to!)

Transgender Law Center

Trans Lifeline

Gender-Affirming Care Fundraising on GoFundMe

Also, please consider subscribing to the trans legislation journalism of Erin Reed, and giving your local congresspeople a call in support of trans rights, with contact information you can find on 5Calls.org.

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