In 2004, Entertainment Tonight did an interview with 19-year-old Ashlee Simpson the day after she performed her first official show for her debut album, Autobiography. In the interview, Simpson is wearing a classic pop-rock-grunge outfit—rings, dark nail polish, a raglan ¾ sleeve tee with “Fancy Pants City” gracing the front, a shiny bell necklace, eyeliner tracing her eyes paired with a touch of grey eyeshadow, and her iconic shaggy mullet. The pop star talks to ET about her nerves for her first-ever show. But when she realizes she’s performing in a room filled with her agents, friends, and family, Simpson “came alive and became a different person.”

Twenty-one years and three kids later, Ashlee Simpson is back in her element—performing for crowds at her “I Am Me” Las Vegas residency, where she’s breaking out fan favorites from her entire discography, such as “La La,” “Boyfriend,” and her smash hit “Pieces of Me.” Originally scheduled exclusively for September 2025, “I Am Me” at the Voltaire Venetian Resort was received so well by fans that Simpson decided to add more dates during the last two weeks of January.

Photography by Jamie Bruce

Simpson is thrilled to return to her pop-star era and reconnect with her devoted fanbase. Much of that bond was forged during The Ashlee Simpson Show, her MTV reality series that chronicled pivotal moments in her early music career. “This is why I do this. It’s been such a reminder to me of that feeling and how we’ve all grown up and evolved, and people have stuck with me throughout all these years,” Simpson says. She points to a recent moment that felt especially meaningful: working on vinyl releases with a fan who has followed her since the Autobiography era. “That was definitely a full-circle moment to get to have that experience of getting to work with her… We gotta do the ‘I Am Me’ (Las Vegas residency) vinyl now!”

Autobiography celebrated its 20th anniversary in July of 2024, and Simpson’s sophomore album I Am Me celebrated its 20th anniversary in October of 2025. Now in the midst of revisiting her past for her Vegas residency, the singer is reconnecting with her younger self. Looking back 20 years, Simpson admits how fearless young Ashlee was. There’s that classic question masters of work get asked: “If you could go back to the moment it all began, what would you say to that version of you?” Simpson responds by saying she would tell 20-year-old Ashlee to trust her instincts and not rush the process. The older and wiser Ashlee also follows with this: “It’s OK to make mistakes. The wins and the mistakes are what shape you and define who you will be.”

Photography by Jamie Bruce

Speaking about her loyal fans, she adds, “They saw what I went through. They were at my shows as I was like ‘that’s not me…’ they were always there. So that was a beautiful experience for me.” Returning to the present, Simpson states that experiencing strong levels of hate during her “I Am Me” era taught her to be tough and resilient. “For me now, having kids, I think it’s something you want to instill in your children.”

Simpson’s daughter Jagger is now a preteen, and she has begun watching episodes of The Ashlee Simpson Show and listening to her mother’s early albums. Seeing Jagger engage with that era has been unexpectedly reflective for Simpson, who recognizes how those songs and stories—once shaped by her own coming of age—are now becoming part of her daughter’s understanding of the world. It also underscores a shift she knows is coming: in just a few years, Simpson will be guiding Jagger through experiences of her own. “It’s such an interesting dynamic being a parent and being a mom, especially to a daughter where you’re like, ‘Oh, I remember feeling this way at that time, at this age.’ At least you’ve got the tools to help them through it.”

Photography by Jamie Bruce

Watching Jagger grow up, Simpson is beginning to notice both echoes of her younger self and clear differences between them. Jagger shares her mother’s silly, playful spirit and loves watching her perform. When Simpson was young, she looked to artists like Blondie and Pat Benatar for inspiration; now, during rehearsals for her I Am Me residency, Jagger and her friends watch wide-eyed from soundcheck (the show itself is 21+), newly discovering the Y2K artists Simpson once shared the charts with. “It’s actually so fun to see her and her friends discover this era of music,” Simpson says.

At the same time, Simpson is enjoying experiencing today’s pop landscape through her daughter’s eyes—especially artists who were inspired by her own music and fearless attitude. When she took Jagger to see Olivia Rodrigo, Simpson found the current pop-rock star to be “such a badass.” “I’ve got to be that for some of my fans and now, to get to see my daughter experience that and who she loves and who she’s drawn to is very exciting,” she adds.

Stylistically, mother and daughter couldn’t be more different. Simpson has always leaned tomboy, while Jagger is unapologetically girly. “She’s definitely way more girly than I am. She’s like, ‘I would never put that look together, Mom.’ Fine!” Simpson laughs. Jagger controls the aux in the car—a G-Wagon, the same model Simpson drove at 20—meaning Simpson is now well-versed in everything from K-Pop Demon Hunters to the global girl group KATSEYE. As for her own listening habits, Simpson has recently been drawn to Lily Allen for her raw honesty, especially on West End Girl and the track “Pussy Palace.”

Photography by Jamie Bruce

As fans speculate about the possibility of new music, Simpson remains creatively active—even while balancing motherhood and her Las Vegas residency. She finds inspiration in quiet moments, especially during car rides, echoing the way she wrote some of her earliest songs in her vintage G-Wagon. Meditation has also become an important way for her to reconnect with herself, a practice that’s hard to sustain in a lively household but especially meaningful when she can carve out moments of silence.

As a believer in New Year’s resolutions myself, I asked Simpson about hers. She recalled welcoming the new year at an early, rainy evening gathering at her sister Jessica’s house—putting the kids to bed, falling asleep before midnight, working out the next day, and once again calling it an early night. From that experience, Simpson summed up how she’s entering 2026 in four words: “Grounded, focused, inspired, and open.”

Photography by Jamie Bruce