Which Pop Stars Won June 2026? Olivia Rodrigo, Taylor Swift, Ariana Grande & More

In 1997, stateside alt-rock was in an unsure enough place that very briefly, a group of ex-ravers from the U.K. were considered the future — with explosive singles, controversial videos, incendiary statements and a truly unprecedented amount of pop star power for a dance act. In this third week of our 2026 kickoff to our annual Vintage Almost-Pop Stardom mini-series — looking at close-but-not-quite pop stars during their biggest years — Tom Breihan of Stereogum joins to talk about The Prodigy's year of MTV dominance, with "Firestarter," "Breathe," "Smack My Bitch Up" and the 'Fat of the Land' album, which the group disappeared immediately after topping the charts with.

In 1995, other alt-rock bands had bigger albums and bigger hits than Hole, but none dominated media and pop culture in quite the same way — mostly due to the increasingly high profile of explosive frontwoman Courtney Love, who became a celebrity thanks to her marriage to late rock icon Kurt Cobain, and spent '95 proving herself an equally iconic and brilliant artist in her own right. In this second week of our 2026 kickoff to our annual Vintage Almost-Pop Stardom mini-series — looking at close-but-not-quite pop stars during their biggest years — Lina Morgan of the Song vs. Song podcast joins to talk about Hole's and Love's greatest year of pop culture centrality, with "Doll Parts," "Violet," MTV Unplugged, Lollapalooza '95, and a particularly unforgettable showdown with Madonna at the MTV Video Music Awards.

In 2006, Arctic Monkeys served as the culmination of a half-decade worth of much-hyped U.K. buzz bands, and finally experienced the biggest breakthrough any group had in its home country since Oasis a decade before — although it took them nearly a decade to make anywhere near the same impact stateside. In this second half of our 2026 kickoff to our annual Vintage Almost-Pop Stardom mini-series, looking at close-but-not-quite pop stars during their biggest years — also be sure to check out part one about 2006 Lily Allen— Thomas Smith of Billboard UK joins to dive into Arctic Monkeys during the group's once-in-a-generation year of 'Whatever People Say I Am, That's What I'm Not' setting records and trends, even though the band couldn't avoid backlash even for the full year.

In 2006, Lily Allen was a much-needed breath of fresh air during a period in pop music that had gotten a little static and stale — although we didn't really get it in the U.S. until the next year, and then never to the same level as in her home country. In this first half of our 2026 kickoff to our annual Vintage Almost-Pop Stardom mini-series, looking at close-but-not-quite pop stars during their biggest years — be sure to also check out part two about 2006 Arctic Monkeys — Sophie Williams of Billboard UK joins to dive into all things Lily Allen during her singular breakout season, the year of "Smile," "LDN," 'Alright, Still,' and mini-feuds with just about the entire pop scene of 2006.

On this Who Won the Month episode of the Greatest Pop Stars podcast, host Andrew Unterberger is joined by Billboard staffers Trevor Anderson and Kyle Denis to discuss the big pop stars, rising prospects and veteran greats who were heard from loudest in September 2026 — who closed out the summer season in pop stardom in style. 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 2026.