The Enduring Bond: Diana Ross and Michael Jackson’s Lifelong Friendship

Diana Ross and Michael Jackson shared a special connection that stemmed from their time together at Motown Records and blossomed into a lifelong friendship filled with mutual love, respect and support. As one of Motown’s biggest stars, Ross took young Michael under her wing, becoming a trusted mentor and confidante as he navigated the pressures of childhood fame. Over the decades, Ross was a loyal and caring friend to Jackson through all of life’s ups and downs. Their enduring friendship weathered challenges, controversies and time apart, lasting until Jackson’s untimely passing in 2009.

Humble Beginnings

Long before she was a globally-renowned superstar, Diana Ross climbed the ranks at Motown in the 1960s as the lead singer of the supremely successful vocal group The Supremes. At the same time, a young Michael Jackson was honing his talents as the precociously gifted frontman of The Jackson 5. Even early on, Ross recognized something special in Michael. “He had this professionalism…he was so outgoing and had such an energy,” she reflected in a 1980 interview. As Motown labelmates, Ross and the Jackson 5 crisscrossed the country together on concert tours, forging a supportive connection that laid the foundation for their lifelong bond.

A Budding Friendship

When Michael struck out on his own as a solo artist in the early 1970s, he often spoke about how much he continued to look up to Diana Ross behind the scenes. “I admire her a great deal. As far as I’m concerned, she’s a genius,” Jackson said in 1979. “I learned so much from watching and being around her.” Michael was enthralled not just by Ross’ commanding stage presence, but also her graciousness and charm out of the spotlight.

As Michael’s star rose meteorically with hit albums like “Off the Wall,” he still made a point to credit Ross for her mentorship. “She’s wonderful. I love Diana very much,” he told Ebony magazine. “I’m crazy about her…She really helped me a lot in the early years with my career.” Throughout Michael’s whirlwind solo success, Ross remained someone whose guidance and affection he could rely on. “She’s a great inspiration. She’s been kind of like a mother to me,” Michael acknowledged while on the cusp of mega-stardom.

A Saving Grace

By the early 1980s, Michael found himself at a crossroads. He had split from Motown, endured family turmoil and was grappling with self-image issues that would lead him to get plastic surgery. Emotionally drained, creatively frustrated and close to bankruptcy, Michael retreated from public life. As he faced this crisis of confidence, Diana Ross once again provided invaluable support. “She’s one of the few people who always held out her hand for me to hang on to,” Jackson revealed to Oprah Winfrey in 1993. Through periods of depression and anxiety, Ross told Michael to believe in himself and boosted him back up with kindness, wisdom and patience. Her unwavering faith helped Michael regain his spark to record and release “Thriller,” which catapulted him to unprecedented global fame as the King of Pop.

Once Michael Jackson reached the pinnacle of music success in the 1980s, his schedule was jam-packed with a non-stop blitz of concerts, music videos and appearances around the world. The relentless pressures of fame took their toll both physically and mentally at times. Even still, Ross and Jackson’s connection endured through it all – she was among the few who understood first-hand the blessings and burdens he shouldered as arguably the most famous man on the planet.

Whenever they could, Ross and Jackson got together for heart-to-heart talks to provide perspective, laugh and enjoy their unlikely yet utterly natural kinship as soul mates. “There’s an intimacy there, a bond that’s very real,” Ross described to Rolling Stone. “Neither of us have to explain anything to each other.” Through the years, Ross popped in for surprise visits at Jackson’s Neverland Ranch; comforted him when scandals rocked his world; lightened his mood with encouraging phone calls; and exuded sympathy and strength as a trusted confidante.

Into the 90s and beyond, Ross and Jackson cultivated their special friendship away from cameras and columns. “She’s so warm and loving…she’s just my main support,” Jackson said after one of their familiar heart-to-hearts. Though often separated by their far-flung superstardom, Ross remained Jackson’s anchor. “I don’t think she realizes to this day how much of an impact she made on my life,” Michael professed in his 2003 documentary. “I owe her so much. She helped me break out of my shell.”

United in Grief

In 2009, Michael Jackson’s sudden death rocked the world, with an outpouring of shock and grief from devastated fans, friends and peers in the entertainment world. Few were more stricken with sorrow than Diana Ross, who regarded Michael like a family member after providing years of close friendship. “He was part of the fabric of my life in a unique way since he was barely in his teens,” Ross mourned. “We shared a bond that was unique, genuine and pure.”

Ross was a pillar of dignity and strength at Jackson’s emotional memorial service. Through tears, she summoned the courage to speak in tribute to her irreplaceable friend: “Michael, when you left us, a part of me went with you,” she uttered, overcome with emotion. “A part of me is buried with your dancing shoes.” Ross leaned on the timeless memories of their connection to carry on Jackson’s creative legacy. “In my heart, I know he will live forever,” she said.

Over a decade since Jackson’s devastating loss, Diana Ross still feels his absence profoundly. “Not a day goes by that I don’t think of him,” she told the Sunday Post. “I miss my little brother very much.” Though Michael Jackson remains immortalized as the greatest entertainer ever, Ross remembers him most poignantly as a sensitive soul – her loyal friend through all seasons. Four decades on, Ross and Jackson’s loving bond still resonates as a transcendent, unshakable imprint. In Ross’ words: “Michael and I shared a bond that was unique, genuine, and pure…we connected in a way that few are able to understand.”