Greatest Pop Stars Podcast
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.
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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.
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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.
It’s been a long lead-up to Lady Gaga‘s new album Mayhem. Aside from the collaborative Love for Sale LP with Tony Bennett and the Joker: Folie a Deux-accompanying Harlequin set — both of which mostly consisted of covers of pop standards — Mayhem is Gaga’s first official album in nearly half a decade, since the […]
Though February is the shortest month of the year, it didn’t feel that way from a pop stardom perspective in 2025. Within 28 days, we got all kinds of major pop events — the Grammys, the Super Bowl, multiple music-heavy celebrations of Saturday Night Live‘s 50th anniversary — as well as several major new releases […]
In 2025, artists from the indie and pop worlds collaborate and co-mingle regularly enough that it’s almost hard to remember a time when it was ever really that novel. But earlier this century, indie and pop were still isolated enough that in 2009, when Solange took her sister Beyoncé and Bey’s husband Jay-Z to a […]
This Valentine’s Day, Drake released his first new album since before his 2024 feud with Kendrick Lamar changed everything about his career outlook and overall narrative — the PartyNextDoor full-length team-up $ome $exy $ongs 4 U. While the final verdict on the album and what it might (or might not) do for Drake’s overall trajectory […]
After taking over Genesis frontman duties for the gone-solo Peter Gabriel in the mid-’70s, drummer-singer Phil Collins had gradually built up his popularity, his industry renown and his pop songwriting prowess over the course of a decade. He’d become a solo star after breaking off from his group in the early-’80s, but continued to gather momentum with the band as well, and also emerged as a go-to collaborator for much of the era’s pop and rock aristocracy. By 1985, it would all come together in one year that saw Collins absolutely flood the zone with hit singles, big collaborations, bigger performances, headline-capturing pop culture moments and even an acting turn on TV’s hottest primetime drama.
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On this Vintage Pop Stardom episode of the Greatest Pop Stars podcast, we look back at Collins’ singular 1985, and examine how an unassuming, plain-looking drummer became one of the most ubiquitous pop stars of the MTV generation. Host Andrew Unterberger is joined by Chris Molanphy of Slate and the Hit Parade podcast to talk all things Phil Collins, as Molanphy shares his memories of becoming a devout (if occasionally slightly abashed) Phil fan as a teen, and Unterberger explains how an unofficial New York-celebrated holiday — one coming up very soon on the calendar — expanded his own love for Phil as a young adult.
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We then dive all the way into the deep end on Collins’ 1985, which started with hits, peaked with hits and ended with even more hits — but in between, also included a gig on Miami Vice as Phil the Shill, appearances on both coasts’ Live Aid festivities (including with a quasi-reunited Led Zeppelin), and an Oscars snub so galling it still rankles the nice-guy pop star to this day. And of course, we do get into those hits, including the agony and the ecstasy of “Do They Know It’s Christmas,” the possibly purloined groove and confusing (in more ways than one) title of “Sussudio,” and the underappreciated knife-in-the-gut divorce rock of “Separate Lives.” We end with the unlikely question: Was Phil Collins actually the Greatest Pop Star of 1985?
Check it out above — along with a YouTube playlist of some of the most memorable moments of Phil’s 1985, 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:
Transgender Law Center
Trans Lifeline
Gender-Affirming Care Fundraising on GoFundMe
The Trevor Project
It’s been a near-year-long road to the Big Game for Kendrick Lamar, whose 2024 crescendoed from March onward, to the point where the rapper — who had long seemed conflicted about the idea of crossover success — ended the year as our editorial staff’s pick for the year’s Greatest Pop Star. He’s picked up right […]
We’re now over a month in 2025, and it’s been an absolutely packed beginning to the year in pop stardom. We’ve already gotten plenty big album drops, tour announcements, breakout hits and viral moments — and then of course, in the last week alone, we’ve gotten two major star-studded events in the FireAid benefit concert […]
On February 8, 2015, nearly everyone in attendance at the Staples Center in Los Angeles expected the top prize at the 57th Annual Grammy Awards to go to Beyoncé. The pop and R&B superstar had changed the game 14 months earlier with the surprise drop of her self-titled album, topping the Billboard 200, drawing unanimous raves and dominating the culture for the entire year to follow. But when it came time for Prince to announce the winner for album of the year that night, a different solo “B” name was called – confusing many in the crowd and watching at home, infuriating one easily excited fellow superstar, and setting into motion many of the narratives that continue to define the Grammys a decade later.
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This week, on the Greatest Pop Stars podcast, we debut our Great Moments in Pop History series, looking at some of the pivotal moments throughout the decades that have come to define our perception of pop music, pop culture and pop stardom. On the precipice of the upcoming Grammys – airing this Sunday (Feb. 2), with one of the most loaded nominee classes in recent memory – we flash back to 10 years earlier, when one of 2025’s preeminent nominees (and the biggest overall winner in Grammy history) lost an album of the year race she was the heavy favorite to win, with Beck’s acclaimed-but-less-impactful Morning Phase instead taking home top honors. It’s a snub the Recording Academy still has not yet made good on, with Beyoncé being nominated and losing in the category twice in the years since.
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Host Andrew Unterberger is joined by Billboard executive digital director (and Pop Shop Podcast co-host) Katie Atkinson – who was in the building that memorable night – to recall everything there is to recall about the 2015 Grammys. We start with everything else of note that happened during those Grammys – like Sam Smith’s early-career-peak night of dominance, the cavalcade of pop megastars performing (but somehow playing zero of their signature hits) and an A-plus-list trio of legends united for one time only. We also run through some of our favorite less-starry performances of the night, including Hozier with a towering Annie Lennox, and Sia with both a wig and Kristen Wiig.
And then, we dig into the nitty gritty of Beck beating Beyoncé – and Kanye nearly crashing the stage in protest – and the impact it all ended up having on the Grammys’ next decade. We remember the double-shock of Beck’s longshot victory combined with Kanye’s oh-no-not-again fakeout, and give context for how bizarre it was (and remains) that Beck, of all people, became the face of Grammy-approved establishment rock. Then, of course, we set our sights on the 2025 awards – where Beyoncé is once again an album of the year nominee, for 2024’s Cowboy Carter – and ask: Is it finally time for the Queen to take home the crown? (And if she finally does this year, will it actually be… kinda weird?)
Check it out above — along with a YouTube playlist of some of the most memorable moments from the 2015 awards — 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!
Welcome to a brand new year of pop star greatness! Our Greatest Pop Stars of the 21st Century and Greatest Pop Stars of 2024 lists are now over and done with, but the race for 2025 has just begun. Explore Explore See latest videos, charts and news See latest videos, charts and news On this […]