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

MTV’s biggest night — and now officially Music’s Most Iconic Night — is just around the corner (Sept. 7), as the Video Music Awards come 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 should be a memorable one — but for no one moreso than whichever artist gets to become the latest 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 this year’s nominees would all be more than happy to add theirs to.

Will that list come to include a repeat winner, like Kendrick Lamar, Lady Gaga or The Weeknd? Perhaps a long-overdue first-timer, like Ariana Grande, Bruno Mars or Billie Eilish? Maybe a newer crossover star like ROSÉ, Sabrina Carpenter or Playboi Carti? We’ll see on Sunday, but before then, take a look back at Billboard‘s ranked list of the 41 videos that have already received MTV’s greatest honor — 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.