Jay-Z and Michael Jackson, photographed backstage at Hot 97’s “Summer Jam” concert at the Nassau Veterans Memorial Coliseum in Uniondale, New York by Walik Goshorn on June 28, 2001. Jigga is wearing Latrell Sprewell’s “8” New York Knicks jersey. 

At the time of his headlining performance Jigga’s beefs with Nas and Mobb Deep were moving from the subliminal to direct interaction. Towards the beginning of his set, after opening with his verse from Mýa’s “Best of Me, Part II,” he had told the crowd that “there’s a lot of shit going on in rap music. A lot of cats yappin’ [but] y’all know what I do—your boy handles his business;” before launching into the first-ever performance of the Kanye West-produced “Takeover” and posting up contestants on the Summer Jam screen. The 15,000-strong crowd was mostly silent during his performance, taking in every single unheard bar and saving their voices for the hardest-hitting lines. However, when Jay dropped the second verse acapella so the crowd could hear very clearly his Prodigy diss lines as they put a 1988 picture of the Queensbridge rapper dressed up for his Grandmother’s dance class on the big screen the crowd went crazy. The rumor is that it was Ashanti who gave Jay the photograph, as she had also been a student at the Bernice Johnson Cultural Arts Center. 

Knowing he had a very-public chance to drive home the point that he wasn’t about to relinquish his hip-hop crown anytime soon, Jay had devised a plan to make his Thursday headlining performance one that would never be forgotten, with his “Takeover” diss just the beginning. 

With DJ Scratch on the decks and Beanie Sigel and Memphis Bleek acting as hypemen, the rest of the Roc-A-Fella Records family lined the back of the stage and danced around with bottles of Cristal in their hands, taking a rhythm lead from the label’s co-founder Dame Dash. As with all of his shows, Jay was like a drill sergeant with the performance—at one point even scolding Bleek on mic because he missed a cue (“Bleek, you’re not focused”). 

VA legend Missy Elliott popped up to first perform “Is That Your Bitch?” with Bleek and Hov, and then her hit single “Get Ur Freak On.” Fellow Summer Jam performer Ja Rule stayed around so he could join Jigga for “Can I Get A…,” but he missed his cue because he was distracted backstage—instead of running the beat back and starting over, Jay told the crowd to “give it up for Ja Rule” and directed him to move off the stage (note: this is when Ja was huge). The famous violin player Miri Ben-Ari (who happens to have the same birthday as Jay-Z) was brought out to add some stringed flavor during “Big Pimpin’.”

If that wasn’t enough, legendary duo EPMD (Erick Sermon and Parrish Smith) came out to perform their 1989 single “So Wat Cha Sayin'”—which Beanie and Bleek had updated (their version being “So What You Saying”) on Beans’ second studio album The Reason, which had released two days earlier. During rehearsals for the show Jay had bet Erick Sermon (who also performed his hit single “Music” during EPMD’s appearance) $1,000 that the crowd would sing along with his fifth verse line “Luther Vandross says, yo I am, ‘Soooo amazing, and I’ve been waiting’.” Erick didn’t believe they would, but he had to pay up when the crowd yelled the lines at him. He handed Jay a stack of bills onstage, and Jay threw the $1,000 into the front row (“y’all can keep that”). 

Even after all of this excitement, the set’s crème de la crème moment came towards the end of the show. After teasing a performance of his Jackson 5–sampling hit single “Izzo (H.O.V.A.)” at the end of his set, Hov announced he had to introduce a surprise guest first: the King of Pop. “I know Michael Jackson better come from behind that motherfuckin’ curtain,” Jay-Z declared to the amazed-but-hestitant crowd, who clapped and cheered as they waited in anticipation for MJ to emerge. Was the King of Pop really in attendance at the rap-heavy event? 

After what must have been the longest 90 seconds of his life, Jay addressed the now-semi-doubtful crowd, saying “You want me to go back and get him myself? Okay, I’ma go get him.” Moments later the two walked out to screams and rapturous applause unlike anything ever heard at Summer Jam before. “Michael Jackson ladies and gentleman, make some noise!” Hov yelled triumphantly. MJ stood next to Jay and struck a b-boy stance with his arms folded, with the superstar’s only words to the crowd being “I love you all” before he exited the stage to the “Izzo” instrumental. 

In a 2009 interview with Britain’s NME magazine Jay reminisced on when MJ “walked out on stage the place went mental. Grown men were grabbing their hats and screaming.” Frequent Jigga collaborator DJ Premier was at the event with Freddie Foxxx and his crew, and he remembers when MJ walked onstage the whole crowd was chanting “Michael, Michael” as loud as he had ever heard. “We were like, ‘it’s really Michael!’ MJ can have that effect on you. You can be the hardest guy out, but when you see Michael it’s over. I told myself, ‘I ain’t coming to no more Summer Jams. I don’t care who performs, I’m good.” 

According to Memphis Bleek, when Michael Jackson arrived his security cleared out the backstage area (as if the President was there) and ordered everyone unauthorized to meet him to stand with their face to the wall when he walked through to the stage. However, with Hov vouching for them, the whole Roc-A-Fella Records team was able to meet the King of Pop and pay their respects, with the Roc-A-Fella photographer Walik Goshorn snapping pictures of them with MJ. The singer had brought his children, Michael Jr. and Paris, with him to New York, and Jay recalls they were “running around backstage having a great time.”  When asked by Vibe magazine in March 2002 what it felt like to join Jay-Z at Summer Jam MJ told the magazine “I just wanted to show up and give him a hug. There was a tumultuous explosion of applause and stomping; it was a lovely, lovely welcome. I was so happy about that. It was a great feeling, there was so much love.” 

WNYE-TV’s “Video Music Box” host Ralph McDaniels was backstage after the show, and asked the King of New York for an interview to discuss his thoughts on what had just transpired on the Summer Jam stage. Jay gathered him team, but as the interview was about to start he told McDaniels, “I don’t want to talk, let them talk.” Jigga stood back with a mean mug, silently signaling to Dame Dash, Memphis Bleek, Beanie Sigel, Freeway and Brownsville boxer Zab Judah to speak on his behalf⁠—seemingly deciding to leave MJ’s legendary guest appearance as his last words for the day. “We the Champions!” Memphis Bleek yelled into the microphone. “It turned out crazy, twenty thousand going wild!” “The King of Pop, the King of Rap: it’s the Roc, you bastards!” Dame Dash exclaimed. “We don’t do much,” Beanie joked, then boasted the events of Jigga’s set were “nothing to us.”

In an October 2003 interview with Sway Calloway for MTV News, Jay would name Mike Jackson’s appearance during his Summer Jam set as one of the biggest highlights of his career. “It was actually easier [to set-up] than what people would think,” a relaxed Hov told the host, “it wasn’t even difficult. I didn’t have to call a hundred times and babysit the situation.” He explained that a week prior to the Summer Jam show he had made a call to Mike to help him clear the “Izzo” sample, and Jackson had begun the conversation by saying how much he had loved Jigga’s 1998 single “Hard Knock Life (Ghetto Anthem),” especially with how Jay’s rhymes were “so in the pocket,” and then he started rapping the first verse over the phone to the stunned rapper. “I was looking at the phone like, ‘You know flow?!’ You forget that Michael Jackson’s not slouch, he’s nice with the music, he really understands it,” Jay told Sway, clearly still in awe. At that moment Hov went for it, telling MJ, “you know, I have this show next week, you should come” and Michael told him “I would love to come, I’ll be there.” During that phone conversation MJ also asked Hov to deliver a verse for a Trackmasters remix of his upcoming single “You Rock My World.”

In a July 2009 interview with the BBC’s Tim Westwood the rap mogul revisited the experience of working with MJ, speaking on how it was “an incredible moment. The fact that Michael Jackson was at a rap concert was mind-blowing to people. To this day I’ve never seen people react like that again for a person. Because, y’know, you don’t get to see Michael Jackson.”  

Two days later Jay and MJ met at Baseline Studios in Chelsea and recorded the “You Rock My World” remix (“That’s a hidden gem right there. I made my Mama proud with that one. My Aunties love me!”). They sent the record to Funkmaster Flex at Hot 97 so he could break it and drop bombs, with Hov once declaring “I think he broke the needles on that one! I think he brought the turntables out that day.” When asked by Vibe magazine in March 2002 why he had asked Jay-Z to contribute a verse to his single he told the magazine “he’s hip, the new thing, and he is loved by the kids today. They love his work. He is tapped into the nerve of popular culture. It just makes good sense.” He told the TV Guide in November 2001 that Jay was “just so sweet. [Anything negative] is so hard to believe. He is so kind, a perfect gentleman.” 

During the studio session Jay played the King of Pop a few tracks from The Blueprint so he could provide feedback on them; and MJ ended up recording [uncredited] background vocals for “Girls, Girls, Girls.” They had soon built a friendship based on a mutual love of music and its complexities. “I remember him calling me and him just talking about, you know, ‘syncopation’ and musician stuff like that,” Jay told NME in 2009. “The Michael Jackson I knew was just a musician who loved music.”

Hov had first met Michael Jackson in mid-1999 while the two were both recording at D&D Studios in New York City. Quincy Jones was also present that day, and Jay asked him for advice on producing and structuring his fourth studio album Vol. 3… Life and Times of S. Carter. Jigga listened to Thriller daily while recording Vol. 3 and he set himself a goal of having nine hot songs on the album that all had single potential, as Thriller did. 

While Thriller was an album that heavily influenced Vol. 3, and Jay says it is “the best album ever made,” it is Off The Wall that Jay counts as his favorite project from the King of Pop. “Off The Wall was one of those albums that was timeless, that didn’t have a genre,” Jay told Rhapsody in 2009. “It was colorless. It was ageless, like me and my mom listen to it together all the time. It was one of those things that the whole family listened to. I think it was a perfect album … I think ‘Thriller’ although was the biggest album, you know had huge records, but these records that were on Off the Wall were so timeless and emotional.”

In his 2017 TIDAL-exclusive Rap Radar interview with Elliott Wilson and Brian “B.Dot” Miller, Hov would say that “Vol. 2 is the Thriller to Blueprint’s Off The Wall.” 1998’sVol. 2… Hard Knock Life is still his biggest selling album, and produced six popular singles. “I’m not talking about chronology, I’m talking about: what Thriller is to Michael is what Vol. 2 is to me. What Off The Wall is to him is what Blueprint [is for me]—the beloved album that everyone loves versus the one that was so big that you gotta call it [a classic].” He then named Reasonable Doubt, Vol. 2, The Blueprint, The Black Album, American Gangster and 4:44 as the six albums he believe deserves classic status. 

Shawn Carter has said that telling his mother, Gloria Carter, that one of her favorite acts had co-signed her son and appeared onstage with him was one of the best feelings he has ever had. “It was fantastic. I could tell my Mama, ‘I’ve arrived.’ Mike liked my flow on ‘Hard Knock Life,’ nobody can tell me nothing. I’m good.” With Gloria Carter and Adnis Reeves being the couple in the neighborhood with the most coveted record collection, listening to The Jackson 5 and Michael Jackson’s solo efforts being played at house parties was a huge part of Shawn’s childhood. 

When Michael Jackson passed away on June 25, 2009 Jay-Z was at the Rocawear offices in Midtown Manhattan and received a page from one of his close friends about the tragic news. He immediately turned on CNN and watched as the station confirmed the rumors. On the six date “Jay-Z & Ciara Live” mini-tour, which began the week after MJ’s untimely death, Jay dedicated a portion of his nightly set to playing MJ classics and asking the crowd to “put your two’s in the air for Michael Jackson, the greatest entertainer of all-time. We don’t mourn death, we celebrate life. So don’t wait until someone is gone to tell them how much you appreciate them.”

In 2013 the Canadian singer Paul Anka revealed that six years earlier he had tried to get in contact with JAY Z to record a verse for the official release of “I Never Heard,: a song he had co-written with Michael Jackson in 1983. He was releasing the song for the first time on his Duets album, but unfortunately Jay never responded to his calls. For the album the song was retitled and released posthumously under the name “This Is It,” in support of the 2009 concert documentary Michael Jackson’s This Is It. In 2002 Hov sampled Anka’s original version of “My Way” on The Blueprint²: The Gift & the Curse’s “I Did It My Way,” as the sample was much cheaper to clear than the famous Frank Sinatra version.

Jay-Z and Busta Rhymes, photographed backstage during the Hot 97 “Summer” Jam concert at the Meadowlands Arena in East Rutherford, New Jersey by Lenny Santiago on June 25, 1999. 

Fresh off their appearances on the record-breaking “Hard Knock Life Tour,” that night fellow Roc-A-Fella Records signees Memphis Bleek, Amil and Beanie Sigel also shared the stage alongside their label boss. During the show nearly 1,000 unticketed fans tried to force their way into the sold-out arena by pushing over a fence and jumping turnstiles.

At the time Jigga was fresh off his record-breaking “Hard Knock Life Tour.” As seen in the tour’s legendary documentary Backstage, an effusive Busta had made cameo appearances along the way. In June 2000 Jay and Busta would cement their friendship by linking up in the studio and producing the hard-hitting “Why We Die” alongside the Brooklyn rapper’s “HKLT” tourmate DMX. Their first appearance on wax together had been the pieced-together “You’re The One (Allstar Rap Remix)” in 1996. Busta names Hov in his Top 5 MCs list alongside Rakim, Biggie, Nas and Eminem. 

Shawn Corey Carter and Trevor George Smith, Jr. both attended George Westinghouse Career and Technical Education High School in downtown Brooklyn, alongside fellow rap legends Christopher Wallace and Earl Simmons. Hov, Busta and Biggie had classes together, and according to Bus-a-Bus they would cut class together so he and Big could go get high. However, Jay “was clean” and didn’t ever smoke weed. 

They once battled in the school’s cafeteria—a battle Hov has repeatedly claimed he won. They no doubt recalled this battle when they toured together on Puff Daddy’s “No Way Out Tour” in late-1997. Busta once delivered the full story in an interview with MTV in 2010, and admitted the three-years-older Jay indeed had him beat: “One day, somebody came up to me and was like, ‘Yo, Jay is in the cafeteria. Do you want to step to him on some rhyme shit?’ So I go. At the time, when we were rhyming, it was speed rap. That was the thing to do. I knew how to freak it, and he knew how to freak it. At the time, he was so ill, ’cause of the people he was with, Jaz-O and the Originators, [that style] was their thing,” Busta explained. “He kind of got the best of the situation. I got to give it up. He was so ill and his arsenal was so long that he had more than what I did. I spit my one rap, and my tank was empty real fast. He came with two or three after that, and I was like, ‘Here we go.’ But I gave it my best. That was probably the fist time that I lost a battle that mattered. [Jay-Z] always exemplified greatness as an MC. He was a scientist with it.” 

In an October 2015 interview with Jimmy Kimmel shortly before the first annual TIDAL X: Brooklyn charity concert Hov recalled the cafeteria battle. When asked who won, Hov responded “I love Busta Rhymes, but…”

In a May 2015 interview with Fuse, Busta named the battle as the moment he knew he had to sharpen his skills if he wanted to be successful. “[Jay] had finessed the speed rapping phenomenally at that time and I was new with the speed rapping, but losing that battle to Jay in speed rapping is what made me one of the most dangerous speed rappers today,” Busta explained. “But Jay knows he can’t see me in no speed rapping today. Nobody can win that war with me.” He also spoke on Jay’s character while at school, saying “he was always clean, well-kept, fresh. He always wore the latest fashion-forward statement. Each day he was draped the right way. The jewelry game was dangerous. Jay was actually the first dude I saw come to school with the Big Daddy Kane Gucci link.”

On June 3, 2008 Barack Obama won the nomination from the Democratic Party to challenge for the role of the President of the United States. That evening Hov, Busta, Diddy, the just-released from prison Damion “D-Roc” Butler, LA Reid and BET Network veteran Stephen Hill celebrated the win by consuming fine food and wine at the Philippe Chow restaurant in Midtown Manhattan. After dinner they headed over to 1Oak in Chelsea to continue the celebrations. During their time there Lil Wayne’s hit single “A Milli” came on and the club (including the famous guests) went absolutely crazy. 

The next day Philli Collins was feeling so inspired by what he witnessed that he headed to his and OG Juan’s Roc The Mic Studios and laid down his “A Billi” remix. That session also doubled as OG’s close friend and Roc affiliate Big Bo’s birthday party, and if you listen closely to the freestyle’s introduction the rap mogul can be heard saying “OG I’m going in! Big Bizzle, happy birthday my nigga!” After Jay had laid down his freestyle with Young Guru working the boards, the group headed to The Spotted Pig for dinner. The “A Billi” freestyle was released five days later.

Jay-Z and T-Pain, photographed performing “D.O.A. (Death of Auto-Tune)” during Hot 97′s “Summer Jam” concert at Giants Stadium in East Rutherford, New Jersey on June 7, 2009.

Just 48 hours earlier Jigga had premiered “D.O.A.” during Funkmaster Flex’s Friday night show; and for the next few days the mood in New York was elevated. The track made an immediate impact on the city and its mindset; and its declarations were played repeatedly on hip-hop stations across the nation. According to The Blueprint 3′s executive producer Kanye West, before they heard the No I.D.-produced beat the album had featured a fair amount of the audio processor. The beat and Jay’s viewing of the Wendy’s “Frosty Posse” commercial caused them to remove all instances of the vocal program on the album.

“I just think in hip-hop, when a trend becomes a gimmick, it’s time to move on,”
Jay said in an interview with Chicago radio station WGCI on June 9. “I saw a Wendy’s commercial and they’re using Auto-Tune. They’re joking on it. It’s like,, ‘Okay, enough of that.’ It was a trend, it was cool in the beginning. Some people made great music with itnow it’s time to move on.”

While talking to Flex and Mister Cee about “D.O.A.” on release night, Jay explained how he was “drawing a line in the sand” and taking aim at the artists who use Auto-Tune as a crutch. In a move

à la 2003′s “Change Clothes,” Hov compared the vocal enhancement usage by rappers to the stagnation of the hip-hop community wearing throwbacks as “a uniform.” “I think I said something important,“ he declared, adding that he spoke out "only on the aspect of moving [the conversation] forward.” 

Jigga also took the time to elaborate on who he wasn’t speaking to, to ensure that no one would take “D.O.A.” the wrong way. “The guys who [originally] did it, did it great,” he explained. “T-Pain, he does great melodies. If you listen to Kanye, great melodies. If you listen to ‘Say You Will’ or ‘Heartless’—great melodies. ‘Lollipop’ was a fantastic melody. Everybody can’t do it. Let them guys do it. They got their little niche, let’s move on. That’s just my opinion. I don’t know if everybody feels the same way.” Upon release T-Pain tweeted: “’D.O.A.’ is the best song I’ve heard in a couple years.” In a hilarious coincidence, the release of the street single coincided with Pain’s reveal of his new $400,000 “BIG ASS CHAIN.”

When Hov appeared on stage that Sunday the SJ crowd were fanatical, and by far made the most noise of the evening. The King of New York had said during his interview with Flex that he would be preoccupied and didn’t have time to make an appearance at the show, so it made for a monumental moment when he swaggered out. At the end of the Snowman’s set Hov came out to rapturous applause to perform ten bars of his “Put On (Remix)” verse; and then stayed to perform his new single for the first time ever. Impressively, the majority of the crowd already knew the entirety of the lyrics and were rapping along at the top of their lungs. 

During the first iteration of the “D.O.A.” hook a surprise guest emerged from the wings. The Auto-Tune-employing T-Pain stood next to Hov. They crossed their arms in unison, and said “goodbye” to Auto-Tune. According to T-Pain—who was headlining the concert that year—the station’s

Vice President of Programming

Ebro Darden had set up the appearance for Tallahassee rapper. "I was going to support Jay’s record [on stage],” stated Pain in a 2017 interview on Power 105.1′s “The Breakfast Club.” “They knew I was coming. The whole thing was set up. The only person that didn’t know was Jay. Ebro set it up.” According to Pain, when he found out Hov was due to perform during the concert he requested that he perform “D.O.A.” during his headlining set. However, Jay had already planned to appear with Jeezy, whom he had signed during his time as President and CEO of Def Jam Recordings

The next day Jay called Angie Martinez during her Hot 97 show, and revealed that the appearance by the King of Auto-Tune was not something he was aware of occurring. “It’s just crazy cause I didn’t know where T-Pain came from,” he laughed. “Remember the concert that T.I. had where 50 Cent walked on the stage? That wasn’t planned either. So I look and I see somebody to my right—I swear I thought he was a fan, like coming over to hug me. I’m not even lying, I’m not being funny trying to take shots. [I’m thinking] ‘That’s some cool rock star stuff!’” Speaking further, Iceberg Slim felt that Pain had bombarded the stage to show rap fans that he was not the intended target of Jigga’s rhymes. “I guess he was trying to be close, and be like ‘Not me!’” Jayhovah theorized. “But it’s really not him. He didn’t mean any harm, he was embracing the record.”

Hov also took the chance to expand on the meaning behind the record, to make himself very clear. “I’m not saying that Auto-Tune is wack,” he spelled out. “What I’m saying is someone does that. You know T-Pain he did it, he writes great melodies, fantastic, Wayne did it and Kanye. You know leave that for them. Not everybody. Like we all gonna make one type of record. Like that’s how you stagnate hip-hop, that’s how people get turned off. You listen to the radio and every single record has  Auto-Tune. That’s corny, that’s wack.”

However, within a few weeks Pain had apparently changed his mind on how he viewed the record, and during a show at the “Rehab” pool party

at the Hard Rock Hotel & Casino

in Las Vegas on September 5 he declared that "Jay-Z is 59 years old! I don’t think he has the right to say what’s good and what’s not. I think if anything is dead, it should be him … To any Jay-Z fans out in the crowd, excuse the fuck outta me. But you don’t see me saying ‘Rap is dead,’ even though it is. ‘Cause apparently all the rappers are trying to do T-Pain." 

In an interview on September 8 with future Roc Nation management client Cipha Sounds and Peter Rosenberg on their Hot 97 show, Jay had a simple response to T-Pain’s statements, saying: “I hope he had a good time, y’know. I just hope he had a great time. Later, when speaking to Ed Lover and Free over at Power 105.1, Jigga’s comments were more revealing. "You have to ask him [why he said that]. I have no idea,” Jay explained. “I said he brought it back, which was cool at the time. I didn’t have a problem with a couple of people doing it, but when a whole genre of music is doing it, then it’s getting lame and it’s not cool to me … I made it very clear I wasn’t talking about him … ’D.O.A.’ was just for the conversation whether you was for it or against it. Obviously some people felt that way … You have to have two sides to have an argument.” As for the comments about Jay’s age, he said, “Well, everybody has a birthday. I just don’t think they have much else to say. They can’t attack my credentials as an artist or my lyrics as an MC. You can’t really attack my lifestyle. What are you going to say about me?”

The very next day Pain spoke with Ed Lover and Free, and expressed how it was the “Summer Jam” performance that threw him off. “I’m ready to go on stage after Jeezy’s set and [the concert organizers] said, ‘Hold on, Jay-Z is about to come out with Jeezy,’” Pain explained. “So I said, ‘Well, Jay-Z [told me he was in] Switzerland.’ They say, ‘No he’s not, he’s right there,’ and I look and there’s Jay-Z. So he gets on the stage and when he gets to the part [on ’D.O.A.’] where he says, ‘I don’t need anyone smiling at this,’ he pointed at me. And then at the end of the song, when I tried to shake his hand, he turned around and said ‘Good riddance.’" T-Pain then proceeded to back away from his Las Vegas comments, declaring that he “feels a lot better. Neither me nor Jay-Z have time to go through this beef crap. I’m a fan of Jay-Z, I’ma always be a fan of Jay-Z.”

On September 30 the

Rappa Ternt Sanga released an apology freestyle titled “More Careful,” which was set over Drake and Trey Songz’s “Successful.” In the track Pain set about making amends for his indiscretions against the King of Rap, with the third verse dedicated to the mini-beef:

“Alright, so lets talk about the Jay shit
Some days I wish that I ain’t never say shit
And Diddy said there ain’t no excuse for what I did
But I felt like he was knocking the same shit that feed my kids
I do music ’cause I need it to make my world spin
So when you down it, it’s like you dissing my girlfriend
And Jay one of the only niggas I hear bringing it
So I didn’t think that he would even entertain the shit
Because entertainment is see through
But if you really feel like I’m dead, then nigga me too
I ain’t trying to write your rhyme
But you could’ve skip one DJ
And all you had to say was "T-Pain, we cool.”
But by all mean don’t take it as a diss or hating
I just want to explain my side of the situation
So if you knew just how much respect I had
You know I’m a real nigga when I say… My bad”

In an April 28, 2010 interview with DJ Chris Styles on SiriusXM, T-Pain said he was “mad as hell” when he first heard “Death of Auto-Tune.” “I was pissed off. I didn’t listen to the song. All I heard was ‘Auto-Tune’ and ‘death.’ Of course that’s my technique, and that’s what I’m known for; so when I hear ‘death of that’ it’s like ‘Wow, the death of T-Pain?’” he revealed. However, as we know, hindsight is 20/20; and Pain soon came to understand the song’s direction. “Y’know, no one really explained it to me. I found it myself. It’s not like anyone came to me like ‘Jay-Z said this, this.’ I always go on iTunes and see what’s hot right now; so I saw the ‘D.O.A.’ part but couldn’t see the parentheses. So I’m like ‘Oh, Jay got a new joint, let’s check it out.’ So i’m listening and it’s like, ‘Good riddance and goodbye’ and I’m like ‘Okay now…’” Pain then revealed when he understood the mistake he had made. “At first it was baffling man, like ‘What did I do?!’ I’m a real big fan of Jay. It was bad at first, but then I started listening to the song and started understanding it wasn’t about me,” he explained. “So then I went to the studio and made the ‘Be More Careful (Successful)’ remix. I figured that was me being a man and admitting where I’m wrong. A lot of people thought I was being soft, but it was my apology as he apparently wasn’t talking to me. I was at shows saying ‘Fuck Jay-Z!’ but then he didn’t even come back at me like that. I was wrong. We met and patched it up. It’s over now.”

As well as the public apology, Pain also delivered a personal apology to Jay one night in a club. “Jay ruffled my hair. Like, ‘Oh, it’s alright,’” he revealed to Marc Lamont Hill in 2014. “He was in front of Beyoncé so I was just like, ‘Alright. Thank you.’ He said something to the effect of, ‘Don’t worry about it.’”

Jay-Z and Snoop Dogg, photographed backstage during HOT 97′s “Summer Jam” festival by Lenny “KodakLens” Santiago on June 25, 1999.

This was the year that headliner Jay dissed the up-and-coming rapper 50 Cent on the stage for the first time. 50 had recently name-dropped Hov on “How to Rob;” his debut single that detailed how he planned to rob numerous prominent figures in the R&B and hip-hop music scene. Hov responded by debuting his track “It’s Hot (Some Like It Hot)” during his set, which included the witty lyric: “Go against Jigga yo ass is dense, I’m about a dollar – what the fuck is 50 Cents?”

During a radio interview with Angie Martinez in 2002, Jigga explained how he was backstage with 50 before he spat the line: “[I told him] ‘Yo, I respect the record, yeah I liked that record, it was hot. But you know I gotta spank you dog!’ That was the conversation. [50 responded] ‘No doubt, do your thing!’ Then it was peace. History … What I respect though is that conversation. It was real.”