Mothers' Love

At the 1999 VMAs, Afeni Shakur and Voletta Wallace, the mothers of slain rappers Tupac and the Notorious B.I.G., appeared, along with Will Smith, to present Best Rap Video (Jay-Z won). Though their sons had been embroiled in a long-running feud, Ms. Shakur said goodbye to all that, declaring, "We stand united as mothers preserving their legacies."

Captions by Genetta M. Adams

Wild West

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Kanye West delivered his infamous "I'ma let you finish …" line when Taylor Swift won the award for Best Female Video in 2009. West, who has a reputation for award-show rants, felt Beyonce's video for "Single Ladies (Put a Ring on It)" should have won. In the end, Bey made the classy move of allowing Swift to speak when "Single Ladies" won Video of the Year.

B.I.G. Tribute

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Puff Daddy delivered one of the most memorable moments at the VMAs with his 1997 performance of "I'll Be Missing You." The song, which features a sample from the Police's "Every Breath You Take," was a tribute to recently slain rapper Biggie Smalls. Puff was joined on stage by Biggie's widow, Faith Evans and ex-Police frontman Sting.

Touchy-Feely

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It seems the MTV Video Music Awards has inspired stars to make some outrageous fashion choices. At the 1999 VMAs, Lil Kim's purple-sequined outfit, which left a breast partially exposed, certainly turned heads. But what got people really talking was when Ms. Supreme Diana Ross reached out and touched Lil Kim's lady part while they were presenting the award for Best Hip-Hop Video.

Who's Bad

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Though other black artists appeared on MTV before him, Michael Jackson truly broke the color barrier with his video "Billie Jean." His groundbreaking video for "Thriller" is one of the most influential videos in history. Jackson's epic opening performance at the 1995 VMA only solidified his hold on the title of King of Pop.

Getting Cheeky

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Prince has always been secure enough in his manhood to wear some racy outfits in his videos and on stage. This was never more apparent than during his performance of "Get Off" at the 1991 VMAs, where he revealed to the crowd a pair of pants with no backside.

Some TLC

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TLC, one of the most successful girl groups in history, suffered a devastating loss when Lisa "Left Eye" Lopes died in a car accident in 2002. The trio had four multi-platinum-selling albums, nine Top 10 singles and a slew of awards, including five VMAs. Surviving members Tionne "T-Boz" Watkins and Rozonda "Chilli" Thomas made their first television appearance after Lopes' death at the 2002 VMAs.

The Kiss

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Newly married Michael Jackson and Lisa Marie Presley attempted to prove their love was real with one of the most awkward kisses ever witnessed during the 1994 VMAs. Before the lip lock, Jackson said, "And they said it wouldn't last." It didn't. The couple divorced in 1996.

Hip-Hopera

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"Trapped in the Closet," R. Kelly's saga of sex, lies and infidelity, began as a five-song set on his 2005 album TP.3 Reloaded. Kelly's so-called "hip-hopera" would earn critical acclaim and become a cultural phenomenon even as he battled child-pornography charges.  During the 2005 VMAs, Kelly previewed chapter 12 by assuming all the roles. The series would grow to 22 installments and eventually be released on DVD.

Hall Mark

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Arsenio Hall, whose talk show was popular with the MTV generation, is the only person to host the show four years in a row, from 1988 to 1991. Only comedian Chris Rock, who helmed the show three different times, would come close to matching the mark set by Hall.