Every VMA Winner for Video of the Year, Ranked: Critic’s Picks

MTV’s biggest night — and now officially Music’s Most Iconic Night — just went down this Sunday (Sept. 7), as the Video Music Awards came to CBS for the first time. Produced for the first time in a decade by longtime MTV exec Van Toffler, hosted by five-time Grammys steward LL Cool J, and featuring performances from a wide array of breakout stars and returning greats, the evening was a memorable one — but for no one moreso than Ariana Grande, who became the latest in a long line of legendary artists to take home the top prize for video of the year.

The video of the year category has a storied but imperfect track record of honoring the all-time greats of the format, acknowledging Madonna but not Michael Jackson, Pearl Jam but not Nirvana, Kendrick Lamar but not Drake. Despite the many celebrated artists and classic videos ultimately denied the distinction, the all-time winners list remains a formidable canon of prime MTV fixtures, YouTube sensations and now even theatrically premiered short films — a list of names that Grande is no doubt overjoyed to now be able to add her own to.

Take a look back at Billboard‘s ranked list of the now-42 videos that have received MTV’s greatest honor — and see where Grande’s Brighter Days Ahead short film ranks among older favorites in our updated list. There’s not a total dud in the bunch, and at least a couple dozen that remain essential pieces of pop culture history years, if not decades later.