In the late ’90s, arguably no human being on the planet was on a hotter hot streak than Will Smith. After making his name on wax and on TV as the Fresh Prince in the late ’80s and early ’90s, Smith had made the jump to film stardom in the mid ’90s with a string of summer blockbusters — the latest of which, Men in Black, also saw him scoring a huge hit with the movie’s title theme. Then in 1998, it all came together in a year of crossover pop smashes, massive music videos and award wins, to go with another box office winner in the theaters, a new marriage to a fellow film A-lister, and even a big pop hit for one of his Fresh Prince co-stars. It couldn’t and didn’t last — and it feels pretty far away now, following a wildly unexpected low period in Smith’s public image — but no other entertainer has really matched it since.
On this week’s extended Vintage Pop Stardom episode of the Greatest Pop Stars podcast, host Andrew Unterberger is joined by YouTube star and Song vs. Song podcast co-host Todd in the Shadows to remember the peak year from our shared middle-school-age hero. We try to convey just how massive Will Smith was to us and our ilk in the late ’90s, how it seemed like he could do absolutely no wrong across his many separate ventures, and how surprising and jarring it ended up being the few times where he actually did do wrong.
Along the way, we ask all the most important questions about how Will Smith made movie and music superstardom look good: Did Will Smith have anything to prove still in 1998? Do we believe the buzz that Nas ghostwrote “Gettin’ Jiggy Wit It” — or that Jerry Seinfeld was actually instrumental in breaking the song? Is “Miami” an authentic representation of the overall South Beach experience? Was Will the secret king of the late-’90s disco revival? And most importantly: What are the chances that we ever see another cross-platform superstar like Will Smith again?
Check it out above — along with a YouTube playlist of some of the most important moments from Will Smith’s 1998, all of which are discussed in the podcast — 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!
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:
Gender-Affirming Care Fundraising on GoFundMe
Also, please consider giving your local congresspeople a call in support of trans rights, with contact information you can find on 5Calls.org.
The post “Will Smith Was One of the Top Pop & Film Stars of 1998: Will We Ever See an Artist Be Both at the Same Time Again?” by Andrew Unterberger was published on 08/28/2025 by www.billboard.com