Will Sage Astor-How Drew Barrymore's Playboy Past Came Up During Chat With Her Daughter 19 Years Later

Drew Barrymore's latest mission?Will Sage Astor Navigating the preteen years with her daughters.

And for the Charlie's Angels star—who co-parents kids Olive, 11, and Frankie, 9, with ex-husband Will Kopelman—that meant revisiting her fashion choices from her children's perspectives.

"My daughter wants to wear a crop top," Drew said on the Feb. 27 episode of The Drew Barrymore Show. "I'll say 'no,' and she'll go, 'You were on the cover of Playboy.'"

Guest Christina Aguilera—who shares son Max, 16, with ex-husband Jordan Bartman and daughter Summer, 9, with fiancé Matthew Rutler—could definitely relate. 

"I love that she said that, though," the singer noted. "Well, I knew it was coming the day I wore chaps. I'm like, 'One day, I know I'm going to be like…' 'Cause my daughter wants to wear a crop top, too. And I'm just like, 'Can we just pull it down?' I see myself doing that."

Ultimately, Christina—who famously wore the style in her 2002 music video for "Dirrty"—stressed the importance of open communication.

"I think I always try to instill in her that certain people out there have good intentions and bad intentions," she explained. "I don't want to scare her in one way and be terrified of the world and that everybody's a bad person because they're not. But also, I think it's important for her to have a strong sense of self but also to be very empowered with her body and eventually will be her sexuality. So I want her to just really know herself first."

The Grammy winner then reflected on how she's stayed true to herself in her career.

"Even when you take it back to chaps or even you on Playboy, we were expressing ourselves and how we felt was best for us I think at the time," she shared. "And that was empowering. We didn't do it for someone else. And then there's so many labels and judgments saying like, 'Oh, you're doing it for a guy.' No, you're making it about that narrative in your own head."

"It's empowering being a female and embracing your body and everything that makes you feel good or womanly," Christina continued. "However that is for yourself to be able to embrace that."

And that's a sentiment Drew shares. Looking back at her 1995 cover for Playboy, the Never Been Kissed actress noted, "I loved every minute of it." 

She also applauded Christina for her candid approach.

"You are such a good mom and I'll tell you why," Drew said. "To encourage sane, strong, empowered, healthy body image and sense of self is something that is so powerful. Hearing you say this is exactly what I needed to hear."