Last year, we ran a super-sized competition to determine the greatest pop song in modern history, from the ’80s to today. Now, we’re back — and this time, it’s all about honoring the best and boldest in music videos.

Madonna has managed to reinvent herself throughout the length of her impressive career, becoming a master at keeping things fresh and innovative for the past few decades -- not an easy feat. But her earliest music videos remain some of her best, and the video for "Vogue" -- which features her iconic Jean Paul Gaultier “cone” bra -- is no exception.

Britney Spears emerged on the pop scene with a bang following the release of the MTV staple  "...Baby One More Time" video, which remains, undoubtedly, the most iconic of her career. Her schoolgirl outfit is one of the most recognizable in pop history, and fun fact: Her assistant Felicitous Culotta played the role of Britney’s teacher, who appears at the start of the video, and the two still work together to this day.

Those are your two choices -- which deserves to move on to the next round? You can vote once per hour until the poll ends on November 25 at 5 PM ET.

Plus, be sure to vote in these other video-battles!

1990s Bracket Semis