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Diana Ross at the Vanity Fair Oscar Party© FilmMagic

Diana Ross’ famous daughter-in-law reveals why she’s not the kind of grandmother you’d think

The I'm Coming Out singer has 8 grandchildren

Tess Hill
News and Features Writer
June 24, 2025
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Diana Ross, 81, is a famous matriarch who is more conventional than some may think. Her daughter-in-law, Ashlee Simpson, 40, recently revealed just what kind of grandmother Diana is.

"She's so hands on," Ashlee told E! News. "She's just about family. And you wouldn't think of [her] like that."

Ashlee described how excited she was when Diana stepped onto the Met Gala red carpet in a long white gown embroidered with her family's names.

Rhonda Ross Kendrick, Callaway Lane, Chudney Ross, Evan Ross, Jagger Snow Ross, Diana Ross, host Tracee Ellis Ross, Raif-Henok Emmanuel Kendrick, Indigo Naess, Ross Naess, and Bronx Wentz pose in the press room during the 2017 American Music Awards at Microsoft Theater on November 19, 2017 in Los Angeles, California© WireImage
Diana and her family

"It was amazing," she remembered. "I was watching them and yelled, 'Everybody hurry down! Ami's on TV!'"

Diana's family

Diana is a mom to five kids. Ronda, 53, Tracee Ellis Ross, 52, Chudney, 49, Ross, 37, and Ashlee's husband, Evan, 36.

The legendary singer has eight grandchildrenRaif-Henok, 16, Callaway Lane, 12, Bronx Mowgli Wentz, 15, Jagger Snow, 10, Leif, 8, Indigo, 7, Everlee, 5 and Ziggy Blu, 4.

Ashlee Simpson, Evan Ross, Diana Ross, and Tracee Ellis Ross arrive for the 2019 Vanity Fair Oscar Party at the Wallis Annenberg Center for the Performing Arts on February 24, 2019 in Beverly Hills, California© Getty
Ashlee spends a lot of time with her mother-in-law

Diana takes her grandchildren everywhere. They attend her shows, hang out at her house, and even tag along to award shows.

In 2019, Diana was honored at the Grammy Awards for her 75th birthday. Her grandson Raif-Henok introduced his 'grandmommy' to the crowd, saying: "She is amazing. Young people like me can look up to her for her independence, confidence, and willingness to be her unique self. She has shown the world that nothing is beyond our reach."

Diana's son Evan married singer Ashlee on August 30, 2015. The ceremony was held at Diana's Connecticut home. She also officiated and performed at the reception.

diana ross in white dress 2025 met gala© WWD via Getty Images
Diana at the Met Gala

After the couple welcomed their first couple in 2015, Evan told PEOPLE: "While [Ashlee] was having the baby, we said we were going to do it just us, but then we saw both our parents behind the curtain watching. Also, those nurses can't stop my mom. Like, Diana Ross just walks in."

During the COVID-19 pandemic, Diana quarantined with Ashlee, Evan, Jagger, and Ziggy, who was just born.

"Right when the baby was born, we quarantined, we did two weeks," Evan recalled to PEOPLE. "[My] mom came and stayed with us, and it was great."

Like mother, like daughter-in-law

Ashlee recently announced that she will perform on August 29 and 30 at the Venetian resort in Las Vegas. The "I Am Me" show is a bit of a comeback and a bit of a celebration of the 20th anniversary of her debut album, Autobiography. 

Photos shared by Ashlee Simpson of her and Evan Ross' son Ziggy's fourth birthday, featuring her mother-in-law Diana Ross© Instagram
Diana celebrating her grandson's Ziggy's birthday

And this performance marks another similarity between her and her mother-in-law. Diana performed 27 shows at the Venetian from 2015 to 2017 for her residency "The Essential Diana Ross: Some Memories Never Fade."

"I would love to steal anything [from her closet]," Ashlee said to E! News. "Anytime she's ever given me anything [to wear], I've been like, 'Oh my god!'"

Ashlee Simpson's daughter Jagger chops off long brown hair

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