The 25 Craziest Moments in VMA History

These will never get old.

Every summer we mark our calendars for the MTV Video Music Awards because we know that it will, without a doubt, be the craziest day of the year. As in epic live performances, can't-look-away-awkwardness, inspiring speeches, major riffs, and "Wait, did he/she really just do that?" double-takes. For a nostalgia-filled stroll down memory lane, look back on these 20 unforgettable moments.

1 of 25
Getty
Miley Cyrus, 2015

When Miley showed up in this and every one of her costume changes thereafter.

Advertisement - Continue Reading Below
2 of 25
Nicki Minaj and Miley Cyrus, 2015

"Miley, what's good?" Nicki Minaj used her acceptance speech of the Best Hip-Hop Music Video award last year to call Miley out for comments she made in an interview. Needless to say, the crowd and the internet were left wondering, "Is this real life?!" 

Advertisement - Continue Reading Below
3 of 25
Getty
Kanye and Taylor Swift, 2015

Six years after the pair's infamous VMA moment, the artists had a very brief period of peace as Taylor Swift presented Kanye with the Vanguard award. Before bringing him to the stage, Swift made a point to call Mr. West "my friend" (with serious emphasis on the friend bit). 

Advertisement - Continue Reading Below
4 of 25
Kanye West (again), 2015

Things continued to get weird after Kanye got to the mic. Though The Life of Pablo rapper is known for rants and outbursts, he outdid himself by announcing his run for presidency in 2020. *upside down smiley face*

Advertisement - Continue Reading Below
5 of 25
Justin Bieber, 2015

The Biebs initially turned heads on the red carpet with an, um, *interesting* new hairstyle. He proceeded to show his emotional side after his performance of "What Do You Mean" when the singer burst into tears! Skip to the end of the video to see the waterworks. 

Advertisement - Continue Reading Below
Advertisement - Continue Reading Below
6 of 25
AP/Getty
Katy Perry and Riff Raff, 2014

At last year's festivities, Perry and Riff Raff arrived in a double denim look that was totally reminiscent of the matching Canadian tuxedos donned by Britney Spears and Justin Timberlake in 2002.

Advertisement - Continue Reading Below
7 of 25
Getty
Miley Cyrus and Robin Thicke, 2013

All eyes were on Miley when she joined in on the "Blurred Lines," fun alongside Robin Thicke clad in nude latex lingerie for some decidedly not-safe-for-the-kids twerking.

Advertisement - Continue Reading Below
8 of 25
Getty
Lady Gaga, 2010

The most extreme of fashion statements, Gaga arrived at the VMAs and accepted the Video of the Year Award for "Bad Romance" wearing a head-to-toe outfit made of raw meat. Yep.

Advertisement - Continue Reading Below
9 of 25
Kanye West and Taylor Swift, 2009

Awkward doesn't even begin to describe our feelings as we watched Swift attempt to accept her award for Best Female Video while being interrupted by Kanye West who proclaimed her fellow nominee Queen Bey made "one of the best videos of all time." While he did have a point, we deem West's behavior thoroughly uncool (but 100% entertaining).

Advertisement - Continue Reading Below
10 of 25
Lil Mama, 2009

We're not sure what compelled Lil Mama to jump on stage during the finale of Jay Z and Alicia Key's performance of "Empire State of Mind," and, uh, yeah we'll leave it at that.

Advertisement - Continue Reading Below
Advertisement - Continue Reading Below
11 of 25
Getty
Britney and Madonna, 2003

There may have been three performers on stage, but all eyes were on Britney and Madonna when they shared a steamy kiss during their performance of "Hollywood." Sorry, X-tina!

Advertisement - Continue Reading Below
12 of 25
Getty
Christina Aguilera, 2002

Aguilera wasn't exactly the girl next store, but we were all saying "whoa" when she debuted her entirely new "Dirrty" look on the VMA red carpet.

Advertisement - Continue Reading Below
13 of 25
Michael Jackson, 2002

In all fairness, this was poor planning on MTV's part, but Jackson accidentally accepted a fake award for "Artist of the Millennium" after Britney Spears deemed him as such while wishing him a happy birthday. *Tugs at collar*

Advertisement - Continue Reading Below
14 of 25
Getty
Britney Spears, 2001

During her performance of "I'm a Slave 4 U," Spears brought out an albino Burmese python, wearing it ever-so-seductively on her shoulders. Now that's dedication to your art.

Advertisement - Continue Reading Below
15 of 25
Getty
Macy Gray, 2001

Knowing the power of a bold red carpet ensemble, Gray used her VMA outfit as an opportunity to plug her new album. The lacey pink and purple dress was emblazoned with "MY NEW ALBUM DROPS SEPT. 18 2001," and "BUY IT."

Advertisement - Continue Reading Below
Advertisement - Continue Reading Below
16 of 25
Diana Ross and Lil Kim,1999

It's our firm belief that Diana Ross can do NO wrong—and we thoroughly enjoyed watching her give Lil' Kim's sequin pastie-adorned boob a friendly jiggle.

Advertisement - Continue Reading Below
17 of 25
Getty
Rose McGowan, 1998

In which McGowan invents what we now call the "Naked Dress."

Advertisement - Continue Reading Below
18 of 25
Getty
Whitney Houston and Mariah, 1998

The soulful songstresses presented at the award show together, which is a lot of diva-licious energy for one stage. Not to mention, they seemingly wore the same brownish, plunging slip gown.

Advertisement - Continue Reading Below
19 of 25
Fiona Apple,1997

Apple's IDGAF demeanor always leaves us awe-struck in the best way, and we can't thank her enough for using her acceptance speech for Breakout Video of the Year to remind us that individuality is king: "This world is bullshit, and you shouldn't model your life about what you think that we think is cool, and what we're wearing and what we're saying and everything," she said. "Go with yourself."

Advertisement - Continue Reading Below
20 of 25
Getty
Spice Girls, 1997

They arrived. Enough said.

Advertisement - Continue Reading Below
Advertisement - Continue Reading Below
21 of 25
Courtney Love and Madonna, 1995

Love gave us so much life when she boldly decided to disrupt Madonna's interview LIVE on TV. Girlfriend has got balls and we love it.

Advertisement - Continue Reading Below
22 of 25
Michael Jackson and Lisa Marie Presley, 1994

After a slightly bizarre speech in which Jackson proclaimed, "Just think, nobody thought this would last," in reference to his relationship with Presley (which, ahem, didn't), the couple shared an even more bizarre makeout sesh.

Advertisement - Continue Reading Below
23 of 25
Madonna, 1990

Madonna's iconic performance of "Vogue," was in a word: Epic. From the Victorian costumes to the theater-like choreography (complete with tongue-in-cheek sexual innuendo) we could watch it over and over again.

Advertisement - Continue Reading Below
24 of 25
Kevork Djansezian/AP
Prince, 1990

Decked out in an ass-less, transparent yellow suit, Prince performed his single "Get Off," fittingly surrounded by nearly-naked dancers in very compromising positions.

Advertisement - Continue Reading Below
25 of 25
Madonna, 1984

During the show's inaugural year, Madge made jaws drop during her stirring, sultry rendition of "Like a Virgin," wearing a wedding dress, on top of a 17-foot cake.

Advertisement - Continue Reading Below
Advertisement - Continue Reading Below
Advertisement - Continue Reading Below
More From Celebrity