The MTV Video Music Awards is always regarded as the coolest party of the year. While it wasn’t once the most anticipated show as compared to its peak during the 90s and early 2000s, a lot of people still tune in and wait for possible iconic moments that the show can possibly offer. In the last decade alone, we saw a three way liplock between Britney, Christina, and Madonna, a bleeding Lady Gaga performing, and the infamous Kanye-Taylor incident. Moments like these make the VMAs a must watch every single year.
Last week, nominations for this year’s telecast have been announced with Justin Timberlake and Macklemore with Ryan Lewis leading the nominations. As for Video of the Year, the nominees were Bruno Mars for Locked Out of Heaven, Justin Timberlake for Mirrors, Macklemore and Ryan Lewis for Thrift Shop, Robin Thicke, Pharell, and TI for Blurred Lines, and the only rose among the thorns, Taylor Swift for I Knew You Were Trouble.
As you may all know, the Video of the Year is the biggest and most coveted VMA. In the show’s 29 years, it has gone to the likes of Aerosmith to Madonna, Eminem to Rihanna, Pearl Jam to Lady Gaga, and both Britney Spears and Christina Aguilera. Now we’ll be ranking the past 29 winners and see which one is the best among the rest in this precious group of winners.
You can click the image to link you to the actual music video. 
29: Britney Spears, “Piece of Me” (2008)
Director: Wayne Isham
Britney Spears has created some of the most engaging music videos among her contemporaries including the now iconic Baby…One More Time in 1999. However, it’s sad to know that her only win for VotY comes from 2008′s Piece of Me. It was not bad video per se, but it’s very obvious that the win was mainly political. After the backlash she received a year prior when she opened the show for Gimme More, MTV made up to her by giving her a mini sweep the following year which included this win for top plum.
28: Don Henley, “The Boys of Summer” (1985)
Director: Jean Baptiste-Mondino
A black and white video that shows the metamorphosis of man in some of the most crucial stages of his life is the main concept of this Don Henley single. While it’s black and white approach helped it, one can’t help but wonder how this, in any way, is the best music video of that year? Even Don Henley can’t help but poke fun at the idea by stating that he won an award for riding in the back of a pick up.
27: Eminem, “Without Me” (2002)
Director: Joseph Kahn
While Eminem’s Without Me video is fun and colorful like any of his past videos, this win gives a been there done that film especially since he already won for a similar and more fun parody video just two years ago for The Real Slim Shady. And while the Survivor, Moby, and Batman jokes were fun in general, it just does not live up to a lot of videos in the list. What’s surprising though is that this also won the Grammy for Short Form Music Video so maybe I’m alone in this train?
26: INXS, “Need You Tonight/Mediate” (1988)
Director: Richard Lowenstein
This music video which combined two INXS singles in one is probably seen as a huge technical achievement during its time. Relying on a lot of visual effects (and an interesting one at that), this win results from the impact it made when it was released more than the longevity it has now. Still, it’s a catchy fun video to watch.
25: Neil Young, “This Note’s for You” (1989)
Director: Julien Temple
In what to be one of the more controversial videos of that year, Neil Young’s video which pokes fun at the concept of rockstars and advertising. It also included a Michael Jackson look-a-like setting fire on his own hair, This Note’s for You was initially banned at MTV as per the request of Jackson’s lawyers. Not only did MTV reconsider their decision, they also decided to reward it with the highest honor that year, ultimately beating Michael Jackson’s Leave Me Alone for the win. How’s that for a one two punch victory?
24: Katy Perry, “Firework” (2011)
Director: Dave Meyers
Every now and then, we see music videos that try to make a statement to the world. That’s what Katy Perry’s Firework exactly did as it addressed issues of homosexuality, confidence in one self, and standing up against others to name a few. Add in some colorful fireworks and the wonderful view of the Buda Castle. But come on, who are we kidding? If there’s one thing you’d remember from this video, it’s Katy Perry’s breasts spewing fireworks left and right. Now how’s that for a statement?
23: Van Halen, “Right Now” (2011)
Director: Mark Fenske
Right Now is a strong song on its own, but with the video containing lots of political statements all throughout, it somehow overshadowed the actual song. It’s a case of two great components (in this case, the song and the video) not bringing the best and ultimately dismissing each other. But yes, it will pass for a great PSA.
22: The Cars, “You Might Think” (1984)
Director: Jeff Stein, Alex Weil, Charlie Levi
The very first winner of the Video of the Year title happens to be CGI heavy one with model Susan Gallagher always seeing the members of the band everywhere she goes. It’s a very tongue in cheek approach for a video, but one that is clearly fun to watch especially with all the technological advancements now. It’s actually not bad for the neophyte win for this category.
21: Panic! at the Disco, “I Write Sins Not Tragedies” (2006)
Director: Shane Drake
With 2006 being the first fan voted VMAs when it comes to determining the winners, we’re sure in bound for a surprise. And yes, we did when newbie rock group Panic! at the Disco winning the top plum for I Write Sins Not Tragedies. On one hand, it’s actually a decent video with the group crashing a circus themed wedding and featured lots of lavish costume designs and art direction. On the other hand, the mere fact that this is the only category they end up winning speaks volumes on the overall perception to the video.
20: Green Day, “Boulevard of Broken Dreams” (2005)
Director: Samuel Bay
It’s surprising to think that Green Day has only won the Video of the Year once, thanks to their career resurgence in 2004-2005. Their win comes for the music video of Boulevard of Broken Dreams which was also their biggest song during this era. What’s particularly striking about this video is the approach that director Samuel Bayer to give the dusty aged feeling of it. It definitely clicked well with the MTV people, as it won five other awards aside from VotY.
19: Christina Aguilera, Lil Kim, Mya, Pink, “Lady Marmalade” (2001)
Director: Paul Hunter
It’s sad to think that Fatboy Slim’s Weapon of Choice lost this award after sweeping the technical categories that year, but with this once in a lifetime moment to reward this diva collaboration by four of the in demand artists during that time is too hard for MTV to resist. That of course, and the fact that they were wearing lingerie through out the video definitely sealed the deal. As Christina Aguilera mentioned in their speech… “The big hair paid off!” Yes honey, it definitely did.
18: Eminem, “The Real Slim Shady” (2000)
Director: Dr. Dre, Phillip Atwell
Eminem’s first win in this category was for the more controversial video of his 2000 breakout song. Making fun of the popstars those days, a humping couple, and hundreds of Eminem clones among others are seen in the insult-filled version of The Real Slim Shady. While he was mostly in hot water during this moment, it also made him a household name during that time, so if there’s ain instance of controversy bringing in the good stuff, it’s definitely this.
17: Rihanna featuring Jay Z, “Umbrella” (2007)
Director: Chris Applebaum
From one two time winner to the other, Rihanna’s first time win here is still for her most iconic song to date. Umbrella, which was a major phenomenon during that time, not only promoted Rihanna from those R&B starlets to a star of her own, the video of her covered in silver paint also garnered positive praises from critics and the public. That’s why it’s no such surprise that it was chosen as 2007′s Video of the Year.
16: Missy Elliott, “Work It” (2003)
Director: David Meyers
Work It gave Missy Elliott a lot of firsts. Not only is this her first video which showcased her immense weight lost, the first single off her Grammy Album of the Year nominee Under Construction, but it was also her first video to win an MTV moonman. Missy might not look like a Halle Berry poster (as mentioned in the song), but she sure is firing in this video, and she can’t help but scream off excitement when she won VotY.
15: Madonna, “Ray of Light” (1998)
Director: Jonas Akerlund
Probably one of the most innovative female divas when it comes to music videos, it is really surprising that Madonna’s only win in this category is for 1998′s Ray of Light. I mean after Like a Prayer, Vogue, and even Take a Bow, this is what gave her the moonman for VotY. While one can easily think of it as a career award, this video which showed Madonna dancing while the whole world is moving behind her makes it an easy call that this merits her a much deserved win.
14: Sinead O’Connor, “Nothing Compares 2 U” (1990)
Director: John Maybury
It’s easy to dismiss this video as simply a close up of Sinead’s face, but what’s magnificent about it is the gamut of emotions that she showed as she sings the lyrics that reminded her of her relationship with her mother. This has been an inspiration to a lot of succeeding music videos showing only the singer’s face, but nothing parallels to the expressions shown here. Plus points to the random Paris shots in the video.
13: TLC, “Waterfalls” (1995)
Director: F. Gary Gray
The 90s has been notorious for making statements and narrating stories through music videos. TLC’s Waterfalls is definitely one of those who benefited from that. Packing in two stories that tackle HIV and drug selling, the sentimental feel of the video plus the shot of the girls dancing in the middle of the ocean (and later in the waterfalls) is a nice throwback of different 90s music video trends.
12: Rihanna featuring Calvin Harris, “We Found Love” (2012)
Director: Melina Matsoukas
The current title holder of this category is once again, Rihanna, only this time, her win comes from her lead single off Talk the Talk. This video with matching narration at the beginning is obviously a throwback to her once relationship with Chris Brown (with the leading man even a spitting image of him), and it went on to depict the relationship she once had with him. Set against the beautiful background of Ireland, this is probably Rihanna’s best video to date and a very deserving second win for her.
11: Dire Straits, “Money for Nothing” (1986)
Director: Steven Barron
In 1986, a completely animated music video is already seen as a big achievement, and I think that’s what pushed Dire Straits for the Video of the Year win. If you watch the music video, you will also be wowed with the technical achievement that it possessed given the time frame of when this was made. Director Steven Barron also helmed two other groundbreaking videos that year, and for that, one can’t say that this one is undeserving of the top prize.
10: Aerosmith, “Cryin’” (1994)
Director: Marty Callnar
Before videoke backgrounds decided to portray stories to accompany the lyrics, 90s rock music videos are also guilty of that. Aerosmith’s Cryin, which tells the story of a teen Alicia Silverstone whose heart was broken by Stephen Dorff, is probably one of their most requested videos. The shot of Silverstone jumping over a bridge and ending up giving a finger to Dorff is still one of the most iconic moments in music video endings. Give yourself a pat on the back if you identified Josh Holloway as the one who stole Silverstone’s bag in the cafe.
09: Lady Gaga, “Bad Romance” (2010)
Director: Francis Lawrence
There’s no better way to start this decade of music videos than with a big bang as Lady Gaga’s Bad Romance won the first Video of the Year for this decade. With dance steps inspired by Michael Jackson’s Thriller and containing some of Gaga’s stripped bare looks, not only does this video ended up with seven moonmen during the VMAs that year, but it also went on to be one of the most viewed Youtube music videos of all time. Not bad for a bad romance.
08: Pearl Jam, “Jeremy” (1993)
Director: Mark Pellington
With a very haunting video that portrays the character “Jeremy” being eaten by peer pressure and dysfunctional families which ended him into taking his own life is probably too much for a music video, but then again, it’s one that perfectly suits the nature of the song. This video has been banned and has been blamed for the cause of non-stop school shooting rampages that happened in the US, which is unfair for the music video. One can argue its connection but one cannot argue the effect it has.
07: OutKast, “Hey Ya!” (2004)
Director: Bryan Barber
Throwing a homage to The Beatles and their 1964 appearance on The Ed Sullivan Show is the primary thing that you’ll notice in this very colorful OutKast music video. Now how this duo managed to portray everyone in the band might involve some visual effect tricks, but it also tripled the fun of the final product. How a fun song can be upstaged by a more fun video is definitely a testament of a great Video of the Year win.
06: Beyonce, “Single Ladies (Put A Ring On It)” (2009)
Director: Jake Nava
Sure, it’s easy to credit Gwen Verdon’s dance routine over at The Ed Sullivan Show as the inspiration for this music video, but we all know that Beyonce surely did bring something to the table that made this an iconic music video with everyone from Justin Timberlake to Queen Latifah to First Lady Michelle Obama jamming to it. It maybe the dancing, it maybe the continuous effect, but whatever it is, it surely made Kanye West believe that “it’s one of the best videos of all time… OF…ALL..TIME!” Okay, Kanye, you win.
05: Peter Gabriel, “Sledgehammer” (1987)
Director: Stephen Johnson
Peter Gabriel’s Sledgehammer is definitely in for the books as one of the most famous and iconic music videos ever. By 1987, it already paved the way for music videos to be memorable and unique and be outside the box in terms of creativity. Combining claymation, pixilation, and stop motion format, it broke barriers and held its own in music video history. There’s a reason why it won a record breaking nine MTV VMAs (a record he still holds until now) and as the most played music video in MTV history. And Brit Gabriel did it by just sitting down in his video. Spell awesome.
04: Lauryn Hill, “Doo Wop (That Thing)” (1999)
Director: unspecified
As the 20th century comes to end, it’s nice to see that the last Video of the Year award for the 90s ended up with Lauryn Hill’s Doo Wop video. For one, it’s a bold statement about the role of women as she juxtaposed a 60s Lauryn on the left of the screen to a modern day 90s Lauryn on the right part. Not only does she present the message via the song, she made it clear what business she wants to say via the video.
03: REM, “Losing My Religion” (1991)
Director: Tarsem Singh
REM not only made a trademark song with Losing My Religion, but they also accompanied it with a dreamy and haunting music video. It’s dramatic, it’s dark, it’s bold, and one that will prompt you to watch for a second and third time. Seems like it was the intention all along which ended up not only with positive word of mouth, but also six MTV Video Music Awards including 1991′s choice for Video of the Year.
02: Jamiroquai, “Virtual Insanity” (1997)
Director: Jonathan Glazer
You know how sometimes after watching a music video, you’d ended up saying “Cool. I wanna try that too.” That’s what Virtual Insanity ended up doing to a lot of those who saw the song’s video. With some sliding floors, animated roaches, and moving sofas, it’s one that every child wants to try. I might not speak for everybody but that’s what I felt like after the first time I see it back when I was still seven. If ever they intend to put hidden meanings among these, I’d never realize, but one thing’s for sure: I’d love to try a moving floor.
01: The Smashing Pumpkins, “Tonight Tonight” (1996)
Director: Jonathan Dayton and Valerie Faris
Sometimes, the best ideas are those that accidentally pop up. The first idea for this video ended up not happening since it’s similar to a Red Hot Chili Peppers video that was just recently launched. This prompted them to go with another that will focus on the audience interpretation of the song, but that quickly fizzled too. The last and final idea that they used is a throwback to the silent film A Trip to the Moon. With limited materials and costumes to use, who would have thought this will end up as a Video of the Year winner and my pick as the best in the show’s 29 year history? Aside from VotY, it also ended up winning five other moonmen making it as the biggest winning video of 1996. Sounds about right.
There you go! What are your favorites among the list above? And which video among the five nominees this year will join the ranks of those above? With the fan voted concept, it’s hard to dismiss Taylor Swift especially since the last six winners here are all pop solo female and she’s the only one who fits the bill. But then again, I can see them finally giving an overdue VotY win to three time nominee Justin Timberlake who is still winless for the top prize. Right now, I’m leaning on JT though I won’t be surprised if it ended up with Taylor winning.
As always, you can follow me on Twitter: @nikowl
