Let’s revisit the time Diana Ross dated Gene Simmons

A little-known fact: The Kiss frontman's influence eventually led Ross to land one of the biggest record deals in history.

You’ve got to be real old school to remember the name Micki Free, who was called in as one of many replacement band members in Shalamar, which probably had more bandmates than hits. Free sat down with VladTV a few months ago and brought up a tidbit that we always forget when discussing the grandest of grand Motown divas, Diana Ross: Her brief relationship with glam-rocker Gene Simmons of Kiss.

Ross is at Chene Park tonight, her first time at that venue and one of a handful of times she’s played here at Detroit at all. (It’s raining, so maybe we’ll get a repeat of that legendary Central Park concert from years ago.) In Free’s interview, he mentions how he was discovered by Simmons and toured with them briefly, then crossed paths again with him a year later with Ross on his arm.

To be clear, none of this is new information, but when we go over the general talking points of Ross, we always go with the Brewster Projects rags-to-international superstar riches tale that includes Florence Ballard, Mary Wilson, Berry Gordy and her famous offspring as supporting characters. It’s not often we deep-dive into those years in between. Let’s take a look back at Ross and Simmons late-'70s/early-'80s courtship.

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Simmons was dating Cher first. Right before hooking up with Ross, Gene was in a high-profile relationship with the ex-Mrs. Sonny Bono. “We just had a wonderful suite at Chicago's Ritz-Carlton overlooking the lake, and Gene said at breakfast that it never ceases to amaze him how comfortable he is with me. He has never had a steady girlfriend, never had a relationship with anybody. That's pretty heavy stuff. He's a very strange, complicated and honest person,” Cher told People magazine back in the day. Unfortunately, Cher and Ross had a falling out after Cher introduced Simmons to Ross. Cher suggested Simmons call Ross about advice for a Christmas gift, but Simmons and Ross’ shopping trip turned into a relationship. Whoops.

Ross was also recently single. We know “The Bodyguard” now as Whitney Houston’s first film with Kevin Costner as her romantic lead. That script was actually written in the 1970s with Ross and actor Ryan O’Neal in mind as the leads. The singer and the actor briefly dated as well.

They had a strange way of appearing in public. KISS is known for their heavy makeup, but in public, they never took it off. So when Simmons stepped out with Ross, they wore handkerchiefs over their faces. “On stage, Simmons dressed like a fire-breathing, vampire-costumed ghoul and was known for the way he would lap his snake-like tongue at his audiences,” J. Randy Tarrborrelli wrote in a biography about Ross. “Part of the gimmick during the time he and Diana dated was that the group was never seen in public without makeup, so whenever the guys ventured out into the world it was with handkerchiers covering the lower halves of their faces. She would sometimes wear a handkerchief too.”

Simmons helped convince Ross to leave Motown Records. Underneath the makeup was a savvy businessman who helped Ross, who wasn’t feeling totally appreciated at Motown (or by Gordy) land what was, at the time, the biggest record deal in history: A $20 million contract with RCA Records. Per "Stop in the Name of Business:" "Simmons was known to be a brilliant and confident businessman and when Diana confided her problems with Motown he said, more than once : 'Get the hell away from there. What are you nuts?' Another source claims Simmons himself strong-armed Gordy into letting her free: “The stranger told Gordy that Ross had an offer from another record company and that if he wanted her to stay at Motown, he would have to match it.”

Simmons’ business savvy rubbed off on Ross. Ross apparently wanted to manage “a guy like Prince,” according to Free’s interview. Ross signed Free to her management company; the guitarist toured with her with Simmons behind the scenes working sound engineering.

The rock-star lifestyle caught up with Ross. Simmons already had a reputation as a womanizer. (Cher told People that he was allowed to have one-night stands on the road.) But the family-oriented Ross wanted more. After a string of “indiscretions,” Ross reportedly wanted Simmons “by her side every single minute.” Their respective fans' disapproval of the relationship didn't help: Diana’s fans saw this rock ‘creature’ as stealing their girl; Kiss fans and band mates saw the high-profile romance as the antithesis of the mystery they felt was a necessary component of who they were. They eventually broke up.

Simmons still speaks fondly of Ross. ''Diana Ross kept me on my toes and I ended up having a relationship with her for two years. I loved that she was such a strong woman who was confident in her own skin. That's the most seductive thing. If a man thinks a woman can live without them, that's it,” Simmons said in an interview. And when a fan asked if Ross attended Michael Jackson’s funeral, Simmons politely responded that she didn’t, suggesting that he's still keeping tabs on her.

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