8 Surprising Ways Diana Ross Is The Ultimate Mother-In-Law To Ashlee Simpson
The unique family dynamic between music legend Diana Ross and her daughter-in-law, pop-rock singer Ashlee Simpson, continues to captivate Hollywood and pop culture fans alike. As of December 18, 2025, the relationship between the two iconic figures remains exceptionally close and supportive, transcending the typical in-law stereotype to become a true mentorship and familial bond. Their connection, rooted in Ashlee's marriage to Diana's son, Evan Ross, is a masterclass in blending two very different entertainment dynasties.
The latest news highlights Ashlee Simpson's candid remarks about her mother-in-law, revealing that Diana is not just a supportive figure but a "hands-on" grandmother and a crucial source of career advice. This deep bond is a testament to the powerful, loving, and sprawling Ross-Simpson family unit, which continues to grow and thrive in the spotlight. Let’s explore the surprising ways "The Boss" has become the ultimate mother-in-law.
The Ross-Simpson Family Dynasty: Key Biographies and Entities
The union of Ashlee Simpson and Evan Ross in 2014 created a new branch of Hollywood royalty, merging the Motown legacy of the Ross family with the pop-rock and reality TV fame of the Simpson family. The family is a sprawling network of influential artists, actors, and entrepreneurs.
- Diana Ross (The Matriarch): Born March 26, 1944. An American singer, actress, and record producer. Rose to fame as the lead singer of The Supremes, becoming a central figure of the Motown sound. She is a recipient of the Presidential Medal of Freedom and a Kennedy Center Honor. She has five children and eight grandchildren.
- Ashlee Simpson-Ross (The Daughter-in-Law): Born October 3, 1984. An American singer, songwriter, and actress. Known for her platinum-selling debut album Autobiography and her reality show The Ashlee Simpson Show. She is the sister of Jessica Simpson.
- Evan Ross (The Son/Husband): Born August 26, 1988. An American actor and musician, the youngest son of Diana Ross and her second husband, Arne Naess Jr. Known for roles in The Hunger Games: Mockingjay – Part 1 & 2 and ATL.
- The Grandchildren: Ashlee and Evan share two children: Jagger Snow Ross (born 2015) and Ziggy Blu Ross (born 2020). Ashlee's eldest child from her previous marriage to Pete Wentz is Bronx Wentz (born 2008), whom Diana Ross also embraces as a grandchild. Diana has a total of eight grandchildren, including Raif, Everlee, Leif, Indigo, and Callaway.
- Other Key Ross Children: Diana’s other children include actress Tracee Ellis Ross, producer Chudney Ross, musician Ross Naess, and singer Rhonda Ross Kendrick.
1. She Officiated the Wedding Ceremony Herself
One of the clearest early signs of Diana Ross’s deep love and support for Ashlee Simpson was her central role in the couple’s wedding. On August 31, 2014, Ashlee and Evan tied the knot in a whimsical ceremony at Diana's sprawling Greenwich, Connecticut estate.
However, Diana’s involvement went far beyond hosting. The legendary singer personally officiated the wedding ceremony, blessing their union with her presence and a short, intimate service. This act cemented her acceptance of Ashlee into the family and demonstrated a profound commitment to her son’s happiness.
The celebration was a grand family affair, with Diana later treating the guests to a performance of two songs, including her classic hit, "Ain’t No Mountain High Enough." The entire event was a reflection of the close-knit and artistic nature of the Ross family.
2. She Is a "Hands-On" and Conventional Grandmother
Despite her global superstardom and status as a music icon, Ashlee Simpson has frequently revealed that her mother-in-law is a surprisingly grounded and "hands-on" grandmother.
Ashlee has shared that Diana is not the kind of grandmother who simply sends gifts from afar. Instead, she is deeply involved in the lives of her grandchildren, including Jagger Snow Ross, Ziggy Blu Ross, and Ashlee’s eldest son, Bronx Wentz.
Diana embraces her role as a famous matriarch who is more conventional in her family life than many might assume. Most recently, Diana was featured in family photos celebrating her grandson Ziggy’s fourth birthday, showcasing her active participation in the children's major milestones.
3. She Gives Crucial Career Advice for Performing
Ashlee Simpson, who is herself a successful pop-rock singer, has returned to the stage for new ventures, including a recent Las Vegas residency. Navigating a return to performing after a hiatus can be challenging, but Ashlee has the ultimate mentor in Diana Ross, who dazzled audiences in Las Vegas for decades.
Ashlee has spoken candidly about receiving invaluable advice from her legendary mother-in-law. The guidance from Diana, a woman who has mastered the art of the live performance, has been instrumental in helping Ashlee prepare for her own shows. This professional support demonstrates a unique and powerful aspect of their relationship, where Diana acts as a trusted industry veteran rather than just a family member.
4. Diana "Has Her Back No Matter What"
Perhaps the most telling sign of their strong bond is the unconditional support Diana offers. Ashlee Simpson has publicly stated that her mother-in-law "has my back no matter what." This statement highlights a deeply personal and supportive connection that goes beyond the surface-level niceties often associated with celebrity in-laws.
This unwavering support is particularly meaningful in the high-pressure world of the entertainment industry, where both women operate. Diana's approval and encouragement provide Ashlee with a solid foundation as she juggles her career, her new residency, and her role as a mother of three.
5. She Inspires Ashlee to Balance Family and Career
Ashlee Simpson-Ross often looks up to Diana Ross as an inspiration for how to manage a demanding career while prioritizing family life. Diana is a mother of five—Rhonda, Tracee, Chudney, Ross, and Evan—and a world-renowned performer, demonstrating a successful balance between her public and private roles.
Ashlee has openly discussed how Diana’s example motivates her to focus on being present for her three children—Bronx, Jagger, and Ziggy—while continuing to pursue her artistic endeavors. This mentorship on life balance is a crucial, non-musical lesson that Diana imparts, reinforcing her role as a true guide.
6. The Ross Family Welcomed Bronx Wentz as One of Their Own
A significant detail that underscores the depth of the family’s acceptance is the seamless integration of Ashlee’s eldest son, Bronx Wentz, into the Ross family.
Diana Ross, Evan Ross, and the entire family have fully embraced Bronx, Ashlee’s son from her previous marriage to Fall Out Boy frontman Pete Wentz, as one of their own. Diana’s love for all her grandchildren, regardless of their parentage, speaks volumes about the warmth and inclusivity of the Ross family dynamic.
7. She Created a Full-Circle Moment in Las Vegas
The connection between the two women and the city of Las Vegas is another remarkable full-circle moment. Diana Ross has been a dazzling fixture in Las Vegas for decades, performing at many of the same iconic venues.
For Ashlee to now headline her own Las Vegas residency in the same city where her mother-in-law achieved legendary status creates a powerful professional legacy. This shared space in the entertainment capital of the world is a subtle but strong link that binds their professional lives together, with Diana having paved the way for the next generation.
8. A Shared Artistic and Musical Legacy
While their musical genres are distinct—Diana in Motown and Soul, Ashlee in Pop-Rock—they share a deep, fundamental understanding of the artistic process. This shared background in music and performance is an essential foundation for their bond.
Diana’s ability to offer specific, relevant advice on touring, performing, and navigating the industry is rooted in a lifetime of experience as one of the world’s most successful entertainers. This common ground ensures that their conversations about career are not just familial encouragement but genuine exchanges between two professional artists, strengthening the respect and admiration between the two women.
The relationship between Diana Ross and Ashlee Simpson-Ross is a beautiful example of two powerful women supporting one another across different generations and genres. Far from a challenging mother-in-law dynamic, Diana is a supportive matriarch, a hands-on grandmother, and an invaluable mentor, ensuring the Ross-Simpson family dynasty continues to flourish.
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