At their best, televised award shows should honor excellence in the entertainment industry while serving as a mile-marker for where popular culture is at a given moment in time. Historically, few ceremonies have done that as effectively and entertainingly as the MTV Video Music Awards. Particularly in the days when MTV had a stranglehold on American youth culture, the VMAs were an annual clearing house of what was new, hot, and on the cutting edge of mainstream pop, whether it be in music, television, athletics, or even politics.
These days, now that MTV has drifted so far from its original mission that it pretty much exists to run episodes of Ridiculousness, the VMAs are more of an outlier for the network. They still represent a decent marker of which pop acts are big at the moment, but as our culture has splintered into stratified niches, there's less of an opportunity to encapsulate the ephemeral pop culture moment in any given ceremony. This was much more feasible in the '90s, and by no coincidence, that's when MTV had its greatest streak of oddball presenters at the Video Music Awards. Sometimes this manifested as mismatched celebrities — like RuPaul presenting with Milton Berle in 1993, or Martha Stewart and Busta Rhymes in 1997. Other times, it was a matter of hooking whatever TV, sports, or news story was hot at that moment and snagging someone to present an award or introduce a performance.
The following VMA presenters were notable not only for being odd inclusions among the Madonnas, Eminems, and Aerosmiths of the music world, but because their mere presence immediately lets you know exactly which moment a given ceremony took place. These are moments very much frozen in time.
Howard Stern (1992): Stern's breakthrough from local radio shock jock to nationally infamous entertainment personality was cresting in 1992. This was the year he proclaimed himself the King of All Media. To commemorate the time when Stern was at his most notorious, it only fits that he'd appear at the Video Music Awards. Of course, not content to just show up as himself, Stern came in character as superhero Fart Man. Descending from the ceiling on wires, in a costume that exposed his comedically underwhelming butt cheeks, Stern joined co-presenter Luke Perry, who pressed his hands to the great cheeks of Fart Man, before the pair presented Best Metal/Hard Rock Video to Metallica for "Enter Sandman."
Rudy Giuliani (1994): Long before he signed on as Donald Trump's bug-eyed hatchet man, Rudy Giuliani was a popular and media-savvy New York City mayor. He appeared on Seinfeld, hosted Saturday Night Live in 1997, and in 1994, he appeared in a vignette with MTV VJs Kennedy and Bill Bellamy to promote that year's Viewer's Choice fan vote. It's not surprising that the mayor of New York would be on hand for the show's' first return to NYC since 1986; it's a little more surprising that any segment on the VMAs would feature two future Fox News mainstays.
Mark Messier (1994): In keeping with the strong New York vibes of the '94 Video Music Awards, the show welcomed hockey star Mark Messier, who only three months prior had led the New York Rangers to their first Stanley Cup championship since 1940. Messier joined MTV VJ Daisy Fuentes on stage to present Best Direction in a Video to Jake Scott for R.E.M.'s "Everybody Hurts." It proved to be quite the memorable moment, as the late Beastie Boy Adam Yauch stormed the stage in costume as "Nathanial Hornblower" in a proto-Kanye West moment to protest Spike Jonze not winning the award for the Beastie Boys' "Sabotage" video.
Monica Seles (1995): Weirdly, the mid-to-late '90s Video Music Awards were really intent on capturing the pulse of the sports world in their given moment. Chalk it up to Dan Cortese and MTV Sports, perhaps. Whatever the reason, the '95 VMAs at Radio City Music Hall took advantage of their proximity to the nearby U.S. Open to lure tennis star Monica Seles, who was playing in her first Grand Slam tournament since being stabbed in the bag by a crazed German fan in 1993. Seles would go on to lose the Open final to her rival, Steffi Graf, but for one brief, shining moment she got to share the stage with Bill Bellamy to explain the voting procedures for the Viewers Choice.
Bela Karolyi (1996): The big sports story of the summer of 1996 was the Summer Olympics in Atlanta, and with that, the triumph of the U.S. women's gymnastics team, on the sturdy leg of little Kerri Strug, who landed a vault despite a broken ankle to win gold for her team, before being swept up in the domineering arms of her Romanian-defector coach Bela Karolyi. While it's not surprising that MTV would gravitate to the big, strange personality of Karolyi, it's kind of weird they opted to have him appear in vignettes with Metallica and Hootie and the Blowfish, rather than Strug, who was the triumphant athlete and actually in MTV's target demographic.
Mark McGwire and Sammy Sosa (1998): Major League Baseball's resurrection in 1998 due to the epic home-run chase between McGwire and Sosa had not yet been tainted by the steroid scandal when the VMAs invited them to introduce the Backstreet Boys' performance of "Everybody (Backstreet's Back)."
Regis Philbin (1999): The Summer of '99 was the Summer of Reege, as Who Wants to Be a Millionaire had captured the imagination of American homes. Clad in one of his signature monochromatic suits and taking his place as the country's most ageless entertainer since Dick Clark, Regis introduced the performance of Fatboy Slim's "Praise You."
Venus and Serena Williams (2000): Once again, the Video Music Awards' proximity to the U.S. Open tennis championships meant they were able to poach the biggest New York City sports event of the moment. This was the year after Serena won the open at age 17 to kick off two decades' of Williams sisters tennis dominance. Two days after the sisters introduced Sisqo's performance of "Thong Song," Venus would take her first U.S. Open championship.
Chyna and Richard Hatch (2000): Two huge pop-culture events in 2000 were the mainstreaming of WWF wrestling via "Attitude" era superstars like The Rock and "Stone Cold" Steve Austin, and the premiere of Survivor, which dominated summer's pop culture conversation. The VMAs procured the first Survivor winner, Richard Hatch, fresh off his victory, and paired him with wrestling's "Ninth Wonder of the World," Chyna. The pair improv'd a little skit which included Chyna (fake?) punching Hatch in the balls, then introduced Christina Aguilera's performance of "Genie in a Bottle"/"Come On Over Baby," a performance that of course ended with a Fred Durst collaboration.
American Idol (2002): The Summer of 2002 was the summer of American Idol, as the British format captured America's attention with its talented singers and mean ol' Simon Cowell on the judging panel. After 9/11, the VMAs had moved their ceremony to August in order to keep away from any memorial undertakings, so the '02 VMAs happened before the Idol season finale. Which meant the moment captured the nation in its brief period of uncertainty with regard to whether Kelly Clarkson or Justin Guarini would emerge as the next great American pop talent. Both Clarkson and Guarini were on hand at the 2002 VMAs, alongside Idol judges Simon Cowell, Paula Abdul, and Randy Jackson. The quintet presented, appropriately, Best New Artist in a video to Avril Lavigne. Clarkson herself would be nominated the very next year for "Miss Independent."
The 2020 MTV Video Music Awards air this Sunday August 30 at 8:00 PM ET/ 5:00 PM PT
Joe Reid is the Managing Editor at Primetimer and co-host of the This Had Oscar Buzz podcast. His work has appeared in Decider, NPR, HuffPost, The Atlantic, Slate, Polygon, Vanity Fair, The Herald Sun, Vulture, The A.V. Club and more.