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

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.

https://5calls.org/

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