If you were alive in 1999, you were watching MTV and the channel’s show Total Request Live. Okay, that might be a slight exaggeration. But the fact of the matter is that TRL boasted many viewers, and they were all drawn to the show’s display of pop music videos.
Videos by American Songwriter
That’s just what we wanted to explore below. We wanted to dive into three music videos from 1999 that were both frequently on TRL and that today still live in our brains rent-free. That’s the power of pop, and that was the power of MTV in 1999! Let’s take a look at some killer pop tunes.
“I Want It That Way” by Backstreet Boys from ‘Millennium’ (1999)
Three words: “TELLLL MEEE WHYYYYYEEEEEEE…” With that short phrase, you were an unofficial member of the pop boy band Backstreet Boys. Indeed, these five-person singing groups were all the rage in the late 90s (and early 2000s), but it was The Backstreet Boys who often claimed the top spot on TRL‘s music video charts. Why? Indeed…. TELLLL MEEE WHYYYYEEEEE!!!
“Genie In A Bottle” by Christina Aguilera from ‘Christina Aguilera’ (1999)
In 1999, pop music was everywhere, and one of the genre’s stars was the up-and-coming vocalist Christina Aguilera. Thanks to her alluring and eye-catching music video for the single “Genie In A Bottle”, Aguilera captured the minds and hearts of many music fans. She was a mainstay on MTV, TRL, and every other music channel known by a three-letter acronym. And she’s still a legend today.
“…Baby One More Time” by Britney Spears from ‘…Baby One More Time’ (1999)
This might be the most famous music video…ever. MTV couldn’t share this offering fast enough when it came out in the late 90s. The vid, along with the single and Britney Spears’ performance, made her an instant star on the pop culture and pop music landscapes. It wasn’t often that you heard people talking about a new music video in the 90s, but high schools were abuzz and all atwitter when this one from Spears dropped.
Photo by Jim Smeal/Ron Galella Collection via Getty Images











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