UNSCRIPTED: Ashlee Simpson

This week, Natalie and Paige spotlight Ashlee Simpson. You know, the younger Simpson sister who stepped out of Jessica’s shadow with a side part, a punk attitude, and a reality show of her own. From her chart-topping debut to that infamous SNL moment, Ashlee’s rise was fast, messy, and unforgettable. The girls break down the highs, the headlines, and how Ashlee handled the kind of public flop that could’ve ended it all, but didn’t. She may have disappeared from the tabloid front pages, but Ashlee’s journey from pop rebel to low-key wife and mom is full of twists you might’ve missed. And yes, we’re still singing “Pieces of Me.” Our Unscripted segment will be moving to its own RSS feed starting January 2026. Until then, you can continue enjoying it right here on this feed. Be sure to follow and subscribe to the new feed so you don’t miss any of the great conversations coming your way! Learn more about your ad choices. Visit megaphone.fm/adchoices