For Jessica Simpson, supporting Ashlee Simpson has been a public affair.
After all, the “With You” singer shared insight into joining her ex-husband Eric Johnson to cheer on Ashlee as she kicked off her “I Am Me” residency on Aug. 29 at the Venetian Resort Las Vegas.
“We are all a big, happy family, so it’s important for all of us,” Jessica exclusively told E! News on the 2025 MTV Video Music Awards red carpet Sept. 7. “We wouldn’t have missed Ashlee, are you kidding me? It was such a moment.”(See all the stars arriving here.)
As a big sister, the artist reflected on the emotional experience of watching Ashlee alongside their parents Joe Simpson and Tina Ann Drew. She admitted, “I was a mess. I cried probably seven times.”
Although Jessica—who shares kids Maxwell, 13, Ace, 12, and Birdie, 6, with the NFL alum—has her own impressive music career, she found herself bumping alongside her little sister’s tracks. The 45-year-old teased, “I think I know her lyrics better than my own old songs.”
For Ashlee, her Vegas residency was a special milestone for her and her husband Evan Ross.
“It was so cool because Evan’s never seen me play a show,” the 40-year-old told E! At the VMAs. “We’ve played shows together, but he’s never actually seen me in action.”
“He was like, ‘Wow, you’re so good,'” she recalled. “I was really touched. It was the sweetest thing I’ve ever seen.”
With Jessica also diving back into music with her new EP Nashville Canyon, Ashlee revealed that she would be interested in having a piece of Jessica in her discography.
“I definitely think that could be in the works, for sure,” she told E! on the red carpet.. “That’s something I think we’d love to do. It’s been fun, both of us in these places, revisiting it and supporting each other and loving each other. And be like little cheerleaders.”
For more stars who attended the 2025 MTV VMAs, keep reading.
—Reporting by Emily Curl
Lady Gaga
In Marc Jacobs.
Sabrina Carpenter
In custom Valentino.
Ariana Grande
In custom Fendi and Swarovski jewelry.
Jessica Simpson
In Christian Siriano.
Doja Cat
In Balmain.
Ice Spice
In Ralph Lauren.
Paris Hilton
In The Blonds.
FKA twigs
Conan Gray
In Erik Charlotte.
GloRilla
In Helen Anthony.
Lenny Kravitz
In Saint Laurent.
Ciara
In Schiaparelli.
Taylor Momsen
Alix Earle
In Tom Ford.
Tyla
In vintage Chanel.
Ricky Martin
Tate McRae
In custom Ludovic de Saint Sernin.
Nicky Hilton
Yungblud
Ashlee Simpson
Malin Akerman
Brittany Snow
Summer Walker
With a Simitri bag.
Megan Moroney
Nicole “Snooki” Polizzi
Mike “The Situation” Sorrentino & Lauren Sorrentino
Sexxy Red
Nikki Glaser
In Ludovic de Saint Sernin.
KATSEYE
In Dolce & Gabbana.
Ty Dolla $ign
