Will Smith, who oversaw the presentation of the award for best rap video, started things off by playing off the title of his 1988 D.J. Jazzy Jeff & the Fresh Prince hit, "Parents Just Don't Understand” (the first winner of best rap video): "I'd like to introduce to you two parents who definitely seem to understand."
The mothers' previously unannounced appearance prompted a standing ovation from a star-studded audience that included Jennifer Lopez, Puff Daddy and Janet Jackson. Shakur spoke first: "In keeping with both our sons' memories and contributions to the arts, we stand united as mothers preserving their legacies."
Wallace added, "The fact that we are even standing here shows what the power of faith, friends, family, loved ones and fans can do to bring us all closer…"
The words were no doubt scripted, but the image was powerful, and said more than they ever could.
The rappers' deaths were, at this point, still fairly recent. 2Pac died on Sept. 13, 1996 at age 25, six days after being shot leaving a boxing match in Las Vegas. Biggie died on March 9, 1997 at age 24 after leaving an afterparty at the Petersen Automotive Museum in Los Angeles.
The idea was born when David Saslow, who was then a vp at Interscope handling video promotion, called MTV's Michele M. Dix with a pitch. "I suggested that Afeni Shakur present an award," Saslow remembers. "Tupac, who was my artist, was nominated for best rap video for 'Changes.'" (The posthumous release appeared on 2Pac's 1998 Greatest Hits album.)
Dix, who was then four years into a 10-year run as a senior creative executive on the VMAs, immediately saw greater potential in that idea. "From there, we talked about having her and Voletta Wallace come together on-stage," Dix remembers. "We both believed it would be an incredibly important and powerful moment to see these two strong women together…Saslow worked to get Afeni on board. We asked our talent team to reach out to Voletta via Bad Boy. I pitched the idea to Will Smith's camp, and it was immediately embraced as a 'Yes, Will is on board.'
Dix thinks Smith was the "ideal" person to present the segment: "He was a well-known celebrity who represented both artistry and kindness. I felt he would embrace the significance of this moment with tremendous respect."
According to Alex Coletti, who produced the VMAs that year for the first of five consecutive years, the entire spot fell into place easily. "I don’t remember any negotiations or speed bumps. I think it was an easy booking, including Will. People wanted something positive to come from all this."
As for the award presentation being more memorable than the identity of the actual winner, Coletti says, "The moments always stick more than the winners. Kayne/Taylor Swift (at the 2009 VMAs) may be the exception, as he was protesting the actual outcome of an award. Soy Bomb (at the Grammys in 1998), Lil Kim and Diana Ross (also at the 1999 VMAs), the moments are what resonate."
Why is that? Coletti, who received three consecutive Emmy nominations (1993-95) for producing MTV Unplugged, offers a possible explanation. "At the end of the day, is one song or video really better than another? That’s a personal preference. Sure, a body of experts can decide, but it won’t change anyone’s mind. But a pop culture moment has no loser. It’s pure entertainment or pure emotion."
For the record, the award went to Jay-Z's "Can I Get A…," a collaboration with Ja Rule and Amil. The track had appeared both on Jay-Z's third album, Vol 2…Hard Knock Life, and the Rush Hour soundtrack. This was Jay-Z's first VMA -- and one of his first major awards, period. The MC capped his brief acceptance speech with a nod to both slain rappers. "B.I.G., 2Pac forever y'all. Hip-hop music."
The sequence is seen today as a classic example of a classy and tender awards show moment. Saslow, who is now an exec vp at Atlantic, notes, "I don't think anyone knew how powerful it would be until after the fact."
Dix has fond memories of the meeting of the two women whom she affectionately refers to as "the legacy moms," sharing the moment from the night that was most powerful to her:
"I was walking with both mothers on the way to stage. They met in the stairwell. This might have been the first time of them ever meeting face to face. Without saying a word, they embraced one another and held each other tight. It was in that moment, I knew what we were planning would have a healing impact on many."