Revisiting Pamela Anderson & Tommy Lee’s Most Cringeworthy Y2K Looks

No, you haven’t stepped into a wormhole back in time to 1999. Pamela AndersonAnd Tommy Lee have returned to the mainstream media—or their story has, at least.

Canadian model Anderson’s career started at Playboy in the early ’90s. Soon after, she began appearing on TV sitcoms like Home Improvement. She cemented her stardom with her iconic designs in 1992. Baywatch role. 

Anderson’s wild child partner and father to her two sons, Tommy Lee, is a founding member of Mötley Crue. The heavy metal band’s debut album was released in 1981. They have remained in the shadow of other rock giants since. 

This duo became famous for another reason in 1997. Amid a turbulent marriage, the couple’s private sex tape was leaked to the internet. 

Hulu’s new miniseries Pam & Tommy looks back on the couple’s tumultuous history. In honor of the show and the cringe-fest that was Y2K, we revisit Pam & Tommy’s wildest looks of the late ‘90s and early 2000s. 

Are you ready to bring back some of your repressed memories

1996: Velour And Glitter

(Vinnie Zuffante/Michael Ochs Archives/Getty Images)

Ah, the look that young love has: eggplant velour and glitter platforms. After their wedding, Anderson and Lee attended the 23rd American Music Awards. Oh, and they got married shortly after they met—about 96 hours later. 

This is how we all came to know and love Pam & Tommy. Why is Tommy wearing an eggplant-velour shirt and leather pants with his leather pants? I believe it is the same reason Pam has Baby Spice-level Platforms on: it was 1996. 

The tiny, tiny facial hair and the sunken forehead feature are a matter of opinion. Well, that’s timelessly Tommy.

1997: No Hat Is Too Big

Tommy Lee and Pamela Anderson at 24th AMAs
(Vinnie Zuffante/Michael Ochs Archives/Getty Images)

A year later, they were at the same event again with a different look. They knew that their sex tape had been stolen at this point. However, the couple knew that nothing was yet out in the open. 

A porn site online obtained the tape and aired it on loop in November 1997. But that was still many months away when this photo was taken. There were still many large hats to wear—the largest, apparently. 

The AMA was graced by the rowdy couple in comically large hats, leather pants (obviously) and fuzzy fur coats (sans shirt). Sex tapes aside, I want to know how Anderson’s fellow passengers fared that night.

1999: Leather, Expanded

Tommy Lee and Pamela Anderson announcing at awards show
(Pascal Guyot/AFP via Getty Images

The year was 1999, Y2K was fast approaching, and Pam & Tommy were still the world’s favorite couple to judge. Anderson and Lee were at a high point in their careers. Their relationship was also at the forefront of their careers. 

And when you’re front and center, you have to put your best face forward. Tommy did this by changing his leather pants to leather overalls. Also, did anyone else forget how much of Tommy Lee’s nipples we had to see in the late ‘90s? 

Anderson looked blonde, buxom, and beautiful—her usual. Still, even she couldn’t escape the Y2K-ness of pencil-thin brows and frosted lips.

1999: The Return of the Statement Hat

Tommy Lee and Pamela Anderson at MTV Music Video Awards
(HennyRay Abrams/AFP via Getty Images

Later that year, Anderson and his wife attended the MTV Music Video Music Awards. Honestly, Anderson’s bottom half slayed. The white corset and sparkly skirt combo look like a Wild West burlesque masterpiece—but the Hats. Why are the hats always the best?

This time, Anderson’s hat is smaller yet louder. It is very similar to the ones that you can buy with 10,000 tickets at your local arcade. Lee arrived in a baggy trench and belted, absolutely zero-tightened outfit. [email protected]$%s given. 

His rubber banded braids are a nice touch to his ecru outfit. So, there’s that.

2003: Beauty and the Beastly

Tommy Lee and Pamela Anderson at Scream 3 premiere
(Frederick M. Brown/Getty Images)

We end our trip down Mötley memory lane with the 2003 premiere of Scary Movie 3. (Yes, it means the Third19 years ago, this franchise was launched. I’m fine, you’re fine, we’re all fine.) 

Again, Anderson looks like a bombshell. Her style might be vampy, but it’s polished. Lee, however? I truly don’t know where to begin. His MO was to make his date look better. 

Lee’s outfit Screams2003 in a way only silky striped tops, baggy trousers and wallet chains can. I would argue this isn’t even the loudest of Lee’s outfits. 

Ultimately, Pam & Tommy were victims of their time. Their wild antics were great tabloid fodder. Combined with Y2K’s rampant sex-shaming, those antics made it easy to forget that the sex tape leak was illegal and non-consensual. 

The love story of Tommy Lee and Pamela Anderson is definitely historic. Its longevity is confirmed by the fact that we’re still talking about that infamous sex tape almost three decades later. 

Hopefully, hindsight can help us illuminate the story’s threads of non-consensual exploitation, misogyny, and hypersexualization. But as for those damned big hats, well, there’s no defending those.

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