Two Generations of Pop, One Trophy: Carpenter and Madonna Take the Duet Prize

Sabrina Carpenter and Madonna left the VMAs with a trophy, taking the award for Best Collaboration for their song "Bring Your Love." The category is judged on the pairing as much as the record, and this one puts two pop names from different eras side by side. For a desk that files red carpets and crowns next to each other, a shared statuette gets the same careful note as a solo win: who won, what they won it for, and on which night.

With reporting from Harper's Bazaar.