Did Justin Timberlake’s 2006 Raise the Bar for Pop Stardom in the Mid-’00s?

This week, Billboard is publishing a series of lists and articles celebrating the music of 20 years ago. Our 2006 Week continues here with a look back at the incredibly triumphant ’06 from the guy who we originally named our Greatest Pop Star for the entire year: Justin Timberlake.

By 2006, Justin Timberlake had already been at the center of the fastest-selling album, the most successful (male) solo-career launch, and the most public-scandalizing moment of the early 21st century in pop music. He didn’t have a ton left to prove among his peers in 2006 — so instead, he set his sights on the all-time greats, with a reinvented sound and image and an album that intended to change a game that was in somewhat desperate need of being changed. And by just about any statistical or intangible measurement, he succeeded wildly.

On this Vintage Pop Stardom episode of the Greatest Pop Stars podcast, 2006 Week continues with a tribute to the Greatest Pop Star of 2006. Host Andrew Unterberger is joined by Billboard executive digital editor and longtime JT superfan Katie Atkinson to discuss Timberlake’s career year, where he topped the charts, defined cool in both music and celebrity, and gave both pop music and pop stardom a long-overdue push forward.

Along the way, we ask all the most pressing questions about 2006 Justin: Did “SexyBack” end up proving itself dated or timeless? Are we gonna give T.I. the benefit of the doubt on being called “Candle Guy”? How catastrophic was the “What Goes Around” music video? Was the stealth Prince beefing more funny or regrettable? How the hell did Black Snake Moan (or Southland Tales) get made? Is “Dick in a Box” still as funny as it was 20 years ago? Does Justin still watch Grey’s Anatomy? And perhaps most importantly: Was there any way that JT could have held on to his cool just a little while longer?

Check it out above, and subscribe to the Greatest Pop Stars podcast on Apple Music or Spotify (or wherever you get your podcasts) for weekly discussions every Thursday about all things related to pop stardom!

Also, check out our editorial staff’s 100 Best Songs of 2006 and 40 Best Deep Cuts of 2006 lists.

And as we say in every one of these GPS podcast posts — if you have the time and money to spare, please consider donating to any of these causes in the fight for trans rights:

Transgender Law Center

Trans Lifeline

Destination Tomorrow

Gender-Affirming Care Fundraising on GoFundMe

Human Rights Campaign – In Your Area