Which Pop Stars Won October 2025? Taylor Swift, Olivia Dean, Tame Impala (?!) and More
On this Who Won the Month episode of the Greatest Pop Stars podcast, host Andrew Unterberger is joined by Billboard staffers Kyle Denis and Stephen Daw to discuss the big pop stars, rising prospects and veteran greats who were heard from loudest in October 2025 — which, spoiler art, was absolutely dominated by Taylor Swift. We each choose our top fives for the month that was, then we talk some disappointing recent performances, and look ahead to who we're most anticipating hearing more from in the final months of the year ahead.
If you enjoy the pod, check out out the rest of our 2025 Who Won the Month recaps here:
https://www.billboard.com/t/who-won-the-month/
Find our YouTube playlist for our October 2025 pop stars here:
https://youtube.com/playlist?list=PLwFs58D1XAMYzWxaQlHOdO2GmvhAaKjml&si=x9oUDOn92fTy-Kkk
And please consider donating to the following causes:
Transgender Law Center
https://transgenderlawcenter.org/
Trans Lifeline
https://translifeline.org/
Destination Tomorrow
https://secure.givelively.org/donate/destination-tomorrow-inc
Gender-Affirming Care Fundraising on GoFundMe
https://www.gofundme.com/c/gender-confirmation-surgery-fundraising
Also, please consider giving your local congresspeople a call in support of trans rights, with contact information you can find on 5Calls.org.
https://5calls.org/
Learn more about your ad choices. Visit megaphone.fm/adchoices
In 2000, D'Angelo was leveling up from R&B phenomenon to full-fledged crossover superstar, with a chart-topping album and a MTV-dominating video — but nearing pop stardom might quickly proved not the best thing for his art or for his spirit. In this third episode of our Vintage Almost-Pop Stardom mini-series — a spin on our usual Vintage Pop Stardom, with four episodes this month looking at close-but-not-quite pop stars during their biggest years — Vulture's Craig Jenkins helps us look back at the late great D'Angelo during the era of 'Voodoo' and "Untitled (How Does It Feel)," and how he helped briefly define the mainstream before pushing away from it to a degree no one could have quite anticipated.
2000 D'Angelo:
In 2011, the worlds of indie and pop were starting to overlap in new and interesting ways — and one of the biggest beneficiaries of the merging universes was Justin Vernon, otherwise known as alt-folk cult phenomenon Bon Iver. In this third episode of our Vintage Almost-Pop Stardom mini-series — a spin on our usual Vintage Pop Stardom, with four episodes this month looking at close-but-not-quite pop stars during their biggest years — Billboard's Kristin Robinson (of the excellent new Billboard on the Record podcast) looks back at Eau Claire's finest during the year when he brushed against pop stardom, both as one of Kanye West's go-to collaborators, and as one of the most-acclaimed, best-selling and most culturally unavoidable artists in all of indie.
2000 D'Angelo Playlist:
https://youtube.com/playlist?list=PLwFs58D1XAMaFV5ppR8JEQ8z5zPiw5X7I&si=N-RxPcxN65_r9oPD
Read Craig's D'Angelo rememberance on Vulture:
https://www.vulture.com/article/dangelo-obit.html
And if you enjoy the pod, please consider donating to the following causes:
Transgender Law Center
https://transgenderlawcenter.org/
Trans Lifeline
https://translifeline.org/
Destination Tomorrow
https://secure.givelively.org/donate/destination-tomorrow-inc
Gender-Affirming Care Fundraising on GoFundMe
https://www.gofundme.com/c/gender-confirmation-surgery-fundraising
Also, please consider giving your local congresspeople a call in support of trans rights, with contact information you can find on 5Calls.org.
Learn more about your ad choices. Visit megaphone.fm/adchoices
In 2011, the worlds of indie and pop were starting to overlap in new and interesting ways — and one of the biggest beneficiaries of the merging universes was Justin Vernon, otherwise known as alt-folk cult phenomenon Bon Iver. In this third episode of our Vintage Almost-Pop Stardom mini-series — a spin on our usual Vintage Pop Stardom, with four episodes this month looking at close-but-not-quite pop stars during their biggest years — Billboard's Kristin Robinson (of the excellent new Billboard on the Record podcast) looks back at Eau Claire's finest during the year when he brushed against pop stardom, both as one of Kanye West's go-to collaborators, and as one of the most-acclaimed, best-selling and most culturally unavoidable artists in all of indie.
2011 Bon Iver YouTube Playlist:
https://youtube.com/playlist?list=PLwFs58D1XAMaFV5ppR8JEQ8z5zPiw5X7I&si=N-RxPcxN65_r9oPD
Subscribe to Kristin's Billboard On the Record Podcast:
https://linktr.ee/billboardontherecord?fbclid=PAZXh0bgNhZW0CMTEAAac0zcDf0Bb1zs_FmhrZTvyHmNNTSlAycNfqX8CAKhhEkjgmz2PQAdSULlz9Kg_aem_h7A5x-8EankWuBCgfc6y8A
And if you enjoy the pod, please consider donating to the following causes:
Transgender Law Center
https://transgenderlawcenter.org/
Trans Lifeline
https://translifeline.org/
Destination Tomorrow
https://secure.givelively.org/donate/destination-tomorrow-inc
Gender-Affirming Care Fundraising on GoFundMe
https://www.gofundme.com/c/gender-confirmation-surgery-fundraising
Also, please consider giving your local congresspeople a call in support of trans rights, with contact information you can find on 5Calls.org.
Learn more about your ad choices. Visit megaphone.fm/adchoices
--------
1:26:23
--------
1:26:23
2005 Paul Wall: Vintage Almost-Pop Stardom (with Jonny Auping)
The long-bubbling Houston rap scene finally took over the mainstream in 2005, getting the entire country invested in tippin’ on four-fours and sittin’ sideways — and the guy who ended up serving as the connective tissue for pretty much the whole moment was The People’s Champ, Paul Wall. In this second episode of our Vintage Almost-Pop Stardom mini-series — a spin on our usual Vintage Pop Stardom, with four episodes this month looking at close-but-not-quite pop stars during their biggest years — Jonny Auping of the My Time Back newsletter helps us look back at the undisputed king of the parking lot during the year of “Still Tippin’,” “Drive Slow” and “Grillz,” as the white rapper-jeweler with the disco ball inside his mouth became one of the most unavoidable figures in popular music.
2005 Paul Wall YouTube Playlist:
https://youtube.com/playlist?list=PLwFs58D1XAMb63lDlLTnzzXuUCvCQwoJD&si=T73JmQ11k_b-n-Yr
Subscribe to Jonny's My Time Back newsletter:
https://mytimeback.beehiiv.com/
And if you enjoy the pod, please consider donating to the following causes:
Transgender Law Center
https://transgenderlawcenter.org/
Trans Lifeline
https://translifeline.org/
Destination Tomorrow
https://secure.givelively.org/donate/destination-tomorrow-inc
Gender-Affirming Care Fundraising on GoFundMe
https://www.gofundme.com/c/gender-confirmation-surgery-fundraising
Also, please consider giving your local congresspeople a call in support of trans rights, with contact information you can find on 5Calls.org.
Learn more about your ad choices. Visit megaphone.fm/adchoices
In 1995, Björk was a phenomenon without a genre, a critically acclaimed singer-songwriter who mixed dance beats with rock attitude and pop flair and became a near-household name without scoring any major hits. In this first episode of our Vintage Almost-Pop Stardom series — a spin on our usual Vintage Pop Stardom, with four episodes this month looking at close-but-not-quite pop stars during their biggest years — Lina Morgan of the Song vs. Song podcast helps us look back at Iceland's greatest musical export during her crossover peak, including her classic 'Post' album, unforgettable videos for "Army of Me" and "It's Oh So Quiet" and even a freelance gig writing for Madonna.
1995 Björk YouTube Playlist:
https://www.youtube.com/playlist?list=PLwFs58D1XAMZyxKrrsXZ6643UOa2BnB1b
Follow Lina on Bluesky:
https://bsky.app/profile/alinaisyou.bsky.social
And if you enjoy the pod, please consider donating to the following causes:
Transgender Law Center
https://transgenderlawcenter.org/
Trans Lifeline
https://translifeline.org/
Destination Tomorrow
https://secure.givelively.org/donate/destination-tomorrow-inc
Gender-Affirming Care Fundraising on GoFundMe
https://www.gofundme.com/c/gender-confirmation-surgery-fundraising
Also, please consider giving your local congresspeople a call in support of trans rights, with contact information you can find on 5Calls.org.
Learn more about your ad choices. Visit megaphone.fm/adchoices
Ireland