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Woodstock '99 in Saugerties, New York

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In the 5 decades since the birth of Hip-Hop, we have watched the evolution from an underground movement to a global phenomenon. As the genre became more at the forefront of pop culture, there have been instances that became key moments in the culture. 

Here, we take a look at the most memorable onstage moments in Hip-Hop history. From the iconic musical performances to the crazy moments that artists pulled off over the years, these are the moments in the culture that made a huge impact, contributing to its place in history. 

Scroll down for our list of memorable onstage moments!

1. DMX at Woodstock ’99

A little over a year after releasing his debut album, It’s Dark and Hell Is Hot, DMX performed in front of a crowd of 200,000 people in New York (and millions more watching at home) during Woodstock ’99, commemorating the 30th anniversary of the original festival. With the mostly-white crowd rapping every word and matching the Yonkers MC’s energy, it was a bright spot in an otherwise disastrous moment in music history.  

2. Outkast Makes A Valid Point At The 1995 Source Awards

While the 1995 Source Awards was mostly remembered for the display of animosity during the height of the East Coast/West Coast rap war, the most poignant moment of the show came from ATL rap group Outkast, who won the award for Best New Group. Approaching the stage to a resounding round of boos from the hostile audience, André 3000 addressed the crowd with one simple, yet lethal statement: “The South got something to say.” 

Nearly 30 years later, the South (and especially Atlanta) is now the epicenter of mainstream Hip-Hop. Looks like 3 Stacks was on to something.  

3. Ol’ Dirty Bastard Crashes The Stage At The 1998 Grammys

What should’ve been a crowning moment for pop singer Shawn Colvin after winning the 1998 GRAMMY Song of The Year ended up being an outrageous moment in Hip-Hop history, courtesy of the ever-entertaining ODB. Still a bit salty about the Wu-Tang Clan losing Best Rap Album to a now-disgraced mogul (who shall remain nameless), he decided to take a moment – Colvin’s moment, to be exact – to vent on stage. 

Wearing his Sunday best, he proudly said, “I don’t know how you all see it, but when it comes to the children, Wu-Tang is for the children. We teach the children, you know what I mean? Puffy is good, but Wu-Tang is the best, OK?” 

We may have to agree on that one.  

4. Kendrick Lamar Unites The West in Juneteenth “Pop Out”

In a proud victory lap in his ongoing feud with a certain rapper from Canada, Kendrick Lamar literally “popped out and showed n****s” during a special concert on Juneteenth. With special guests including Dr. Dre, DJ Mustard, and many more, K. Dot united the West Coast in a way that we have not seen in years. After running through several hits, Kendrick capped off the night by performing his mega-hit, “Not Like Us,” a whopping 5 times, back to back. Needless to say, it served as the final nail in the coffin of a memorable rap feud.  

5. Jay-Z & Nas Squash Their Beef

On to another memorable rap beef, the nearly-decade-long feud between East Coast rap legends Jay-Z and Nas had its fair share of lethal punchlines, low blows, and memorable tracks. It was so nasty that very few people thought they could bury the hatchet. However, in October 2005, the two MCs did the unthinkable and squashed their beef on stage during Jay’s “I Declare War” tour. Nas was invited to perform “Dead Presidents” and “The World Is Yours” during the tour stop in Rutherford, NJ. Afterward, Jay declared, “All that beef sh–is done, we had our fun,” he said. “Let’s get this money.” 

6. Drunken Kanye West Interrupts Taylor Swift’s VMA Moment

In what we should’ve seen as a sign of things to come, a drunken Kanye West decided to crash pop star Taylor Swift’s acceptance speech at the 2009 MTV VMAs. Swift, who should’ve been enjoying her first VMA win for Best Female Video, was rudely interrupted by Ye declaring, “Yo, Taylor, I’m really happy for you, I’ma let you finish, but Beyoncé had one of the best videos of all time!”  

Thankfully, Queen Bey showed a lot more grace, forgoing her own acceptance speech for Video of The Year to invite Taylor to finish her speech. Today, Taylor and Beyoncé are still very supportive of each other as the two biggest icons in music today. As for Taylor’s relationship with Yeezy…no comment.  

7. Lil Mama Crashes Jay-Z & Alicia Keys’ VMA Performance

In another memorable moment from the 2009 VMAs, Jay-Z and Alicia Keys closed out the show with the first-ever performance of “Empire State of Mind.” During the rap anthem’s climax, fellow New Yorker Lil Mama felt compelled to hop on the stage and join in the moment. 

The spontaneously innocent moment, unfortunately, resulted in tons of backlash, which took a toll on the “Lip Gloss” rapper’s mental health. “I was hurt. I was depressed,” she admitted on a recent episode of The Jay Hill Podcast. “I was like, ‘What’s going on?’ You got everybody telling you you’re doing bad. People pointing at you like, ‘What did you do?'”

Thankfully, both Jay-Z and Alicia forgave the young MC for the incident long ago, with Jay saying in a Twitter Spaces conversation, “Things happen. Of course, we love her… yes, she’s forgiven. It’s all love, and she was coming from a place of love it’s just… may have been a little too excited.”

8. Beyoncé Announces 1st Pregnancy at 2011 MTV VMAs

On to another memorable VMA moment! After her performance of “Love On Top” at the 2011 ceremony, Beyoncé

unbuttoned her jacket to reveal that she was expecting her first child, daughter Blue Ivy. From the glow on Bey’s face to hubby Jay-Z’s jovial reaction as he and (a more sober) Kanye celebrated, needless to say, it was the story that rocked the entire world.  

Today, the now 12-year-old GRAMMY-winning Blue Ivy is seemingly following in her famous parents’ footsteps. She learned from the best.  

9. 2 Pac Returns To The Stage (Via Hologram) at Coachella 2012

16 years after he was tragically gunned down in Las Vegas, 2Pac made an unexpected return to the stage. In a moment that shows just how far technology has come, a hologram of the late rapper appeared on stage with Dr. Dre and Snoop Dogg in a memorable performance at Coachella in 2012. Hearing the realistic hologram greet the crowd at a festival that was founded three years after his death could be described as both amazing… and a bit eerie.  

10. VERZUZ Trifecta Of Chaos – Bone Thugs-N-Harmony vs Three 6 Mafia

VERZUZ served as a highlight for Hip-Hop during the pandemic, as artists gather via Zoom to battle it out with their biggest hits. However, once the world opened back up, the webseries went to a whole new level with in-person battles. Unfortunately, it also came with some not-so-shining moments. One such moment came from the match-up between Bone Thugs-N-Harmony and Three 6 Mafia.

As Bone Thugs performed “Buddah Lovaz,” Bizzy Bone called out Three 6 Mafia for disrespecting him while performing his verse. Some “colorful” words were exchanged, a member of Bone’s camp threw a water bottle, and the two groups were on the verge of throwing hands. Thankfully, security quickly calmed things down, and the battle resumed after a few minutes.   

11. VERZUZ: The Lox vs Dipset

What was supposed to be a battle between two iconic NY collectives proved to be a chaotic night in more ways than one. From the trash talking that started weeks before the battle to the brutal freestyling (not to mention an appearance by iconic ring announcer Michael Buffer), The Lox and Dipset did their best to represent for all of New York. 

However, it was clear that The Lox was more prepared for the fight, with Jadakiss calling out Dipset for using backing tracks with vocals. They were not afraid to pull out the big guns either, playing Cam’ron’s former rival Ma$e’s “24 Hours To Live” and name-dropping Jim Jones’ rival Max B. 

Needless to say, this was a battle that had a clear-cut winner. 

12. VERZUZ: Jeezy vs Gucci Mane

Wrapping up the VERZUZ trifecta is the battle between longtime rivals Jeezy and Gucci Mane, which proved to be chaotic from the start. It started with an inspirational message from Stacey Abrams, encouraging viewers to vote in Georgia’s 2020 Senate runoff. Then… Gucci immediately dropped a diss record. 

The two MCs, who had a major falling out after the success of their 2008 hit “So Icy,” went back and forth, with Gucci consistently choosing to go for low blows, even after Jeezy made a point about the many rappers who have lost their lives over the past few years. 

Thankfully, the battle ended on a high note with the pair finally ending their feud with a joint performance of “So Icy,” followed by, apparently, a trip to the club. All’s well that ends well in the ATL.

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