In 1999, Jay Z and DMX embarked (and majorly cashed in) on the Hard Knock Life Tour. Although Jay Z’s album gave the tour its name, the lineup was a joint headliner of the Roc-A-Fella Records co-founder and DMX. Both artists had become the flagship acts at Def Jam Records in the Lyor Cohen and Kevin Liles era of the famed record label. Joining them on the road was another #1 album maker in Method Man (who had been at the label longer than Jay or X), Ja Rule, Memphis Bleek, Beanie Sigel, DJ Clue, Amil—and the decade-long statesman of Def Jam, Redman.

Captured in the documentary film Backstage, Jay Z and DMX had vastly different demeanors on wax, on stage, and as celebrities. While both were pillars of Rap-made-right and suddenly sex symbols, they only overlapped in skill and love of the art. DMX had released two #1 albums in 1998, and occupied a hardcore space in mainstream Hip-Hop that pulled from ONYX, Scarface, and an artist he was often compared to in Tupac Shakur. Earl Simmons brought a jailhouse mentality to the top of Billboard, with his grimace, Newport-smoking, tattooed and shirtless image.  It’s Dark and Hell Is Hot and Flesh Of My Flesh, Blood Of My Blood had their catchy hits, but were anchored by sinister themes, personal confessions, and a man who truly identified himself as a cornered dog. Jay Z, on the other hand, had applied two albums of non-fictional hustling allegories, street-certified truisms, and proving that he “knew what girls liked” (too) into his most Pop-savvy LP yet. Jay pushed his pinky finger out when he toasted champagne flutes to cashmere thoughts-actualized. Shawn Carter was cool, calm, and untouchable—in the John Gotti sense. Vol. 2…Hard Knock Life afforded Jigga his first #1 LP, on the strength of owning his status and diversifying his nimble flow.

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Jay and X joined Eminem, Big Pun, and Nas as the perceived new kings of Rap in ’99. The artists had the sales, the acclaim, and the ability to present their styles on a grand, Pop-embraced level. Notably, DMX and Jay Z had history dating a long way back before “Money, Cash, Hoes,” “Blackout,” and the tour. From above and beneath Manhattan, respectively, X and J would meet on the island for a famed mid-1990s battle. Said to be filmed by the late Big L, the clash of the two MCs would take place atop a billiards table, with lots of cued up lyrics—and a captivated crowd.

Speaking with The Drink Champs Podcast earlier this year, DMX would reflect on the battle, noting that there were “a couple ones” between the Brooklyn and Yonkers MCs near the 13-minute-mark. While the battle is often reported to be in the Bronx (according to many spectators), X says it was in Harlem. “Ruff Ryders had ‘Harlem Nights.’ It was on 135th & Broadway—the project building right there. Jay’s crew was Original Flavor.” Original Flavor was signed to Atlantic Records, consisting of Ski, T-Strong, and DJ Chubby Chub. Jay would appear on two songs on 1994’s Original Flavor sophomore, Beyond Flavor—including single “Can I Get Open?” Ski (n/k/a Ski Beatz) would produce extensively on Jay’s early solo singles and Reasonable Doubt debut. “It was their battle,” X continued. I was the big gun on Ruff Ryders. [Jay Z] was the big gun with them niggas. It wasn’t [known as] Roc-A-Fella then. Dame Dash was there [though].” Dame managed Original Flavor for a time, before establishing his own label with Jay, and Kareem “Biggs” Burke.

There, N.O.R.E. asked the guest who won. “I did. I never lost a battle! I never lost a battle! Never! Never! I’m a battle rapper!,” declared an animated X. His thought process appeared to be interrupted as he was about to compliment his battle foe. “One thing I can give Jay Z is…” is all viewers got. However, Dark Man X is adamant that he is undefeated.

Sauce Money, an affiliate of Jay’s and Clark Kent, says guns were drawn at the battle–in the crowd. “Niggas pulled out guns while they was rhyming. Niggas was pulling out hammers because how we did it was, we had to get on top of the pool table on one end and the other end,” he said (via a 2013 Doggie Diamond interview). Sauce also believes that Jay lit up X. “We were kind of in X’s backyard. They said it was a tie, but that was bullshit. Jay ate that nigga,” said the former Priority Records MC. “You can tell when somebody won a battle, when you’re in somebody’s backyard, and they’re calling it a draw. When you’re in somebody’s backyard, even when that person lose, they’re saying he won.” Waah Dean, one of the Ruff Ryders’ founders who promoted the event, has a different view. “It was so close that we kept it mutual. They would’ve gone on an extra five hours if we had let it be.” Ski also errs on the side of the artist who he worked with most. “In my opinion, to me, Jay-Z just had a little more finesse because of his style. But DMX was incredibly dope. He could not take that away from DMX. [DMX] was a fuckin’ star.” All three detailed the event in a 2011 HipHopDX feature. History has its varying opinions of all legends.

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In 1994, Jay and X appeared to have a seemingly amicable rivalry at an exciting time for Hip-Hop, especially in New York City. That pair would work together in 1995 on Mic Geronimo’s “Time To Build.” Produced by Irv Gotti (who would work extensively with both MCs), the song featured a Jay and an X who had both paid lots of industry dues while looking for an ideal situation. In 2011, Irv Gotti would allege that Jay’s lyrics in the song are actually directed towards DMX. The Murder Inc. founder and Ja Rule mentor also told Complex that DMX “hated” Jay Z. Those were not his words, but in 2016 X alluded to their relationship beginning at odds, thanks to these battles in the ’90s. Despite that, the two would not make it seem as such to the public. With Irv Gotti as the plausible glue in the relationship, X, Jay, and Ja Rule recorded two hard-headed jams in “It’s Murda” and “Murdergram,” and reportedly toyed with becoming a super-group. That never happened.

Even on tour in the late ’90s, DMX and Jay Z were still battling—perhaps the second battle DMX alluded to. The rivalry was not changed by the plaques, money, and hit records. These artists were still true to their roots, and it appeared for both proud egoist men, there were scores to settle. No longer on pool tables with guns on display in the room, these artists were still jockeying for rank in a way much more Rakim and Big Daddy Kane than LL Cool J and Canibus.

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By the millennium, were Jay Z and DMX collaborating, appearing in each others videos, and touring the world together as a facade? Def Jam had re-branded itself in the era of the Black-owned boutique label, following an early-mid 1990s reign in California by Death Row Records. There, alleged tensions between artists caused turmoil within the label. Tupac Shakur and Dr. Dre had a reportedly contrarian relationship in their brief time together, while cousins Snoop Dogg and Daz Dillinger would eventually feud as well.

DMX and Jay’s relationship following the Hard Knock Life Tour may be just as intriguing as it was before their success. X would release three more albums at Def Jam—all #1, all platinum (none featuring Jay). Jay continued to escalate critically, commercially, and venture beyond music. While X’s Blood Line Records’ biggest claim may be signing Yung Berg early in his career, Jay would be the artist responsible for bringing Kanye West (as well as Rihanna, Rick Ross, and Young Jeezy) to the masses. However, during Jay Z’s tenure as label president (following the partnership split and sale of Roc-A-Fella), DMX would leave quietly and bitterly—reportedly due to a change in resource allocation and a feeling of directional shift. The label that X had made truckloads of money for would leave the Dog without a home–only to return to the same Columbia Records system that shunned him in the mid-’90s.

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That’s the way it’s seemingly been for a dozen or so years. Jay Z has become one of the most recognizable faces on the planet. Meanwhile, DMX has stayed in the trenches—battling the law (and serving lots of time), doing spot date shows, and releasing music that leaves fans questioning whether or not it belongs in the same lineage as those first five LPs. In June, DMX spoke to The Breakfast Club about Jay Z. The MC stressed that he’s past his anger at his onetime collaborator. “As strong as I am, to walk around holding anger weighs you down. I ain’t got to be mad at anyone…I got too much other shit to focus on; I got 14 kids, man.” In that same interview, he revealed that Jay and X have not spoken in some years.

Right now Jay Z is in an odd season of his career. In 2016, the mogul has made a song that owned his past, and threw a finger at his critics in Pusha T’s “Drug Dealers Anonymous.” Jay did as he did 15 years ago, he hopped on the season’s hottest song for a rewind-worthy remix verse in Fat Joe & Remy Ma’s “All The Way Up.” Moreover, Jay appears to be giving another collaborator (who may not be a real friend) the business on DJ Khaled’s “I Got The Keys.” So many of these traits seem less like a suit-wearing multimedia mogul, and more of the doo-rag wearing, Cristal-swilling lyricist in the Tyrone Wheatley jersey. In his own words, Jay is “in a good place,” and that’s putting it mildly. The Roc Nation owner has made peace with is past too—he’s snapped photos laughing it up with former partner Dame Dash, welcomed Beanie Sigel back to the fold, and turned an olive branch into a smash hit with Fat Joe (leveraging his Tidal music service in the process).

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DMX, true to his art, is much more conflicted. While the Yonkers, New Yorker is actively performing his hits with the physical energy and stamina that most 45 year olds would dream of, he admits his flaws—and alludes to an ongoing debilitating battle with addiction. In two interviews this year, the Ruff Ryders superstar has been moved to tears (including the one above) on this subject, as it relates to his faith. The MC who says he brought Eve and The L.O.X. to Ruff Ryders, (plus mentored Swizz Beatz) needs his solid ground to step forward. He still commands performances and carries star power almost 10 years since he’s had a single on the charts, and is capable of a comeback—but it may take help beyond himself. Swizz reported that Kanye and Dr. Dre are expected to come forth to give the dog some musical bones.

Jay Z has never conceded that he lost a battle to DMX. However, as he’s clearly winning the war, Hip-Hop could benefit from a re-connection between Jigga Man and Dark Man X, as two of Rap’s most respected titans continue to cement their legacies 20 years later.