Sisters Jessica and Ashlee Simpson got our 2000s radars a-buzzing with their appearance at the 2025 MTV Video Music Awards together. Jessica got her start in the entertainment industry in 1999 with her music hits such as "Sweet Kisses" while her younger sister Ashlee Simpson was still finding her path. The "These Boots Are Made For Walkin" singer also went into reality TV in 2003 with her popular show on MTV called Newlyweds: Nick & Jessica with her former husband Nick Lachey.
Early 2000s
In 2004, Ashlee began her singing career and her own reality TV show called The Ashlee Simpson Show. Although the two shared the same spaces in the industry, they remained immensely supportive of each other. Ashlee shared with Today: "We're sisters. For us it's not about competition. If she succeeds, then I'm happy, and if I succeed, then our family wins no matter what."
During Ashlee's performance on Saturday Night Live in the same year, the entertainer was revealed to be lip-synching however, her big sister Jessica came to her defense and insisted to Digital Spy: "Ashlee is an amazingly talented person and the fact that people are calling her 'Milli Vanilli' is absolutely obscene and ridiculous. She's already sold three million records which is more than I sold in two years. She's proved herself."
Mid-2000s
The "Pieces of Me" singer returned the favor in 2009 when Jessica was being body shamed in the press. Ashlee expressed to TV Guide: "I am completely disgusted by the headlines concerning my sister's weight. All women come in different shapes, sizes, and forms and just because you're a celebrity, there shouldn't be a different standard." During Ashlee's public divorce from Pete Wentz in 2011, the star stayed at her big sister's house as part of her healing journey.
Late 2000s
During 2018, Ashlee went on to partake in a new reality TV series called Ashlee+Evan during which she expressed the sisters' close-knit bond on the series and shared: "My sister and I have a really cool relationship. We've always definitely supported each other through everything that we've done."
When Jessica published her New York Times best-selling memoir Open Book in 2020, Ashlee lovingly wrote on her social media: "I am so very proud of my beautiful, brave, kind, loving sister!!! It's beautiful to see you sharing your truth with the world. You are so inspiring. I love you so much. You are a #1 best-selling author."
Two years later, Jessica shared a selfie of the duo enjoying a fun night and charmingly captioned it: "Got glammed up with my ride or die last night. Ash and I each have 3 kiddos and danced like we were in our 20's again. So. Much. Fun…Sister Pride." Fast-forward to 2024, and Jessica got divorced from her husband Eric Johnson, and Ashlee was there for her older sister's love issues, the same way that she once was.
Ashlee's big comeback
In August 2025, Ashlee made her big stage comeback after almost two decades, when she performed at her debut show for her I Am Me residency in Las Vegas. Jessica put aside her differences with her former partner Eric, as the two watched Ashlee take the stage on August 29.
Jessica showcased not only her maturity but also her dedication to be there for Ashlee, regardless of who's in attendance. During the MTV Video Music Awards red carpet on September 7, Jessica recalled the unique situation at Ashlee's performance. She expressed to E!: "We are all a big, happy family, so it's important for all of us. We wouldn't have missed Ashlee, are you kidding me? It was such a moment. I was a mess. I cried probably seven times."