Greatest Pop Stars

On this Who Won the Month episode of the Greatest Pop Stars podcast, host Andrew Unterberger is joined by Billboard staffers Kyle Denis and Rebecca Milzoff to discuss the big pop stars, rising prospects and veteran greats who were heard from loudest in May 2026 — which was largely defined by one guy with his triple album drop, but also included a couple big country stars and pop legends getting fans excited about new and old releases. 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 summer of 2026.

If you enjoy the pod, check out out our Who Won the Month recaps for the first two months of 2026 and all 2025 here:

https://www.billboard.com/t/who-won-the-month/

And please consider donating to the following causes:

Transgender Law Center

https://transgenderlawcenter.org/

Trans Lifeline

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Destination Tomorrow

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Gender-Affirming Care Fundraising on GoFundMe

https://www.gofundme.com/c/gender-confirmation-surgery-fundraising

Human Rights Campaign – In Your Area

https://www.hrc.org/in-your-area

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/
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It's late May, which means that the race for Song of the Summer is about to be officially underway! With many of the likely frontrunners already established — and some big artists about to cast their lot with much-anticipated new releases — Greatest Pop Stars host Andrew Unterberger is joined by AJ Marks of r/Popheads and the Main Pod Girl podcast to preview the battle to come. We talk about the heavy hitters — led by Ella Langley, Drake and Olivia Rodrigo — while also giving a few minutes for a few longshot contenders and some of our perfect-world picks.

Find a Spotify playlist of some of AJ and Andrew's personal summer favorites here:

https://mainpodgirl.libsyn.com/

Subscribe to Main Pod Girl here:

https://mainpodgirl.libsyn.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

Human Rights Campaign - In Your Area

https://www.hrc.org/in-your-area

Also, please consider giving your local congresspeople a call in support of trans rights, with contact information you can find on ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠5Calls.org⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠.
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The entire music-listening and social-media-habitating world was stormed this past weekend by the man who calls himself Tsunami Papi, with Drake dropping three new albums at once: 'Iceman,' 'Maid of Honour' and 'Habibti.' On this week's Pop Star Performance Review episode of the Greatest Pop Stars podcast, host Andrew Unterberger is enjoyed by Billboard Hip-Hop's own Big Three — Carl Lamarre, Michael Saponara and Angel Diaz — to analyze what the triple-release means, how it's been received thusfar by the online masses, and what it might do to finally take Drake out of the precarious position he's been in for the past two years.

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

Human Rights Campaign - In Your Area

https://www.hrc.org/in-your-area

Also, please consider giving your local congresspeople a call in support of trans rights, with contact information you can find on ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠5Calls.org⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠.
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Today, we wrap up our Janet Jackson Vintage Pop Stardom Week on the Greatest Pop Stars podcast! After visiting Janet in her 'Control,' 'Rhythm Nation,' 'janet.' and 'The Velvet Rope' eras of '86, '90, '93 & '98, we now find the pop icon single and feeling good in her 'All for You' run, and being celebrated simultaneously as a contemporary hitmaker and pivotal legacy artist. Host Andrew Unterberger is joined by Billboard senior charts and data analyst Trevor Anderson as we do it all for Janet one more time, recapping her final year of no-doubt superstardom and imagining a future where everything doesn't go so wrong just a few years later. Check it out here and make sure to catch up on the rest of our Janet Jackson week right before her 60th birthday this Saturday.

Check out a YouTube playlist of Janet's biggest 2001 moments, all of which are discussed in the episode, here:

https://youtube.com/playlist?list=PLjyxjlx5MpVAuy5Fuy2byWaAIFmBihbch&si=3AJJ94-iV8yJDqZe

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

Human Rights Campaign - In Your Area

https://www.hrc.org/in-your-area

Also, please consider giving your local congresspeople a call in support of trans rights, with contact information you can find on ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠5Calls.org⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠.
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We're four years into Janet Jackson Vintage Pop Stardom Week on the Greatest Pop Stars podcast! After visiting Janet in her 'Control,' 'Rhythm Nation' and 'janet.' eras of '86, '90 & '93, we now find the pop icon rejecting her ever-growing bigness for something more personal and intimate. Host Andrew Unterberger is joined by Lina Morgan of the Song vs. Song podcast as we head past the 'Velvet Rope' and deep into one of Janet's richest and most rewarding eras, based around an album that underwhelmed commercially and critically but is now rightly considered perhaps her finest overall work. Check it out here and come back for one final look at the pop icon's peak run — in 2001, at her legacy peak — right before her 60th birthday this Saturday.

Check out a YouTube playlist of Janet's biggest 1998 moments, all of which are discussed in the episode, here:

https://youtube.com/playlist?list=PLjyxjlx5MpVBqA9Ho--37APhqO2E7JFxP&si=5DvQBrDIKb3ZrotM

And make sure to subscribe to Song vs. Song here:

https://www.patreon.com/songvssong

And follow Lina on Bluesky here:

https://bsky.app/profile/alinaisyou.bsky.social/post/3mlniu4vsys2e

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

Human Rights Campaign - In Your Area

https://www.hrc.org/in-your-area

Also, please consider giving your local congresspeople a call in support of trans rights, with contact information you can find on ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠5Calls.org⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠.
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