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 competiti

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