Drew Barrymore and Hilary Duff Look Back At Their Fashion Hits And Flops In Game “Y2K Yay Or Nay” On ‘The Drew Barrymore Show’: “Who Did That To Me?”

On today’s episode of The Drew Barrymore Show, host Drew Barrymore welcomed actress and fellow former child star Hilary Duff onto her show. In between Duff promoting her children’s books and new home fragrance line, she joined Barrymore for a game called “Y2K Yay or Nay,” which had them reflecting on some of their looks from the early aughts to decide whether or not they should bring certain items back in vogue.

“I remember in the ’90s, the ’70s were really hot, and now it’s 20 years later and the Y2K is all the rage,” Barrymore began shortly before kicking off the game with the first two images, depicting younger versions of each actress wearing a skinny scarf.

“You look so much cooler than me!” Duff said, prompting Barrymore to take her hand and push back to assert that Duff looked good, too. Duff, however, wasn’t so easily subdued.

“You guys, my hair color. Who did that […] to me?”

Still, they both ended up saying “Yay” to the skinny scarf look before turning to an audience member decked out in a vibrant sweater to help them decide on the next look, a sweater poncho. While the audience member said “Yay,” both Duff and Barrymore reacted to their past looks with regret.

The next look of choker necklaces produced a much more favorable response from all, including the next chosen audience member, who Barrymore dubbed “the most stylish gentleman here.” A unanimous “Yay” had the two swiftly moving on to the next look, “newsie caps: Yay or Nay?”

The images of the actresses capped up even prompted Barrymore get out of her seat as she recalled what her particular look was for. “I was going to the Rolling Stones concert in Vegas with Cameron [Diaz] and Lucy [Liu],” she said, referring to her two Charlie’s Angels co-stars.

“And I got way too drunk and was in the hallway late that night going, ‘I’m an independent woman!’ And they were like ‘Yeah, yeah, yeah, get in the room,’ and I was like, ‘No, no, no, I’m an independent woman. I’ll do what I want. I’ll let you know when I’m ready to go back in the room,’ and they just shuffled me in,” she recalled.

When Barrymore turned the question back around on Duff to ask where she was going in her cap, the latter didn’t have quite as vivid a recollection. “I have no idea,” Duff responded. “There’s a whole part of my life that I don’t recall where the photos are from.”

However it was their last debate over scented lip gloss that spurred the greatest tangent. While it was an immediate “Yay” for both Duff and the studio audience, Barrymore still made sure to bring out some samples to make sure.

“I mean, I’m going cherry,” Duff said, “Cherry, like Katy Perry, the cherry chapstick.” Barrymore immediately leaned into the discussion of Perry’s hit song, “I Kissed a Girl,” responding, “Why is that lyric so gosh darn sexy? It’s so hot.”

Duff laughed, “Drew had an experience that she’s remembering,” prompting Barrymore to double down, adding “Because girls are so sensual, too.”

Barrymore then pulled out a different flavor and claimed it smelled like “doll hair,” but when Duff took a whiff for herself, she had to disagree. “I can’t smell that,” she said, before trying again to no avail. “What is it? Do I have COVID? What’s wrong with me?”

After they went back and forth sniffing, Barrymore ended the segment trying to put her guest at ease, joking “I’m getting doll hair. Maybe something’s wrong with me!”