Jay-Z, photographed as he headed to his ringside seat for the Mike Tyson vs. Orlin Norris Heavyweight fight, held at the MGM Grand’s Garden Arena in Las Vegas on October 23, 1999.

Jigga had been at Tyson’s successful return to the ring against Francois Botha after serving a 15-month suspension for biting Evander Holyfield’s ears in their June ’97 fight. However his return to the top was halted once again as shortly after that January ’99 victory Tyson was convicted of having assaulted two motorists in Indiana the year before and sentenced to one year in prison. He served four months and was released in June to resume training. In his second highly-anticipated return to the ring Tyson defeated Botha in round one after the former sustained a knee injury when knocked down by Iron Mike after the bell.

Jay-Z and Dame Dash, photographed as they arrived at the MGM Grand’s Garden Arena to watch the Mike Tyson vs. Francois Botha fight in Las Vegas on January 16, 1999. Jigga is wearing a Roc-A-Fella Records leather jacket and an Iceberg Snoopy sweater.

This bout was the return of Tyson to the ring after being banned for 15 months for biting Evander Holyfield’s ears in their June ’97 fight. Iron Mike won the match by knocking out Botha in the fifth round. This was a great outcome for the rapper too: as a fellow Brooklynite Jay was so devastated when a then-undefeated Tyson lost his 1990 fight to Buster Douglas in Tokyo he felt “physically hurt” himself.

Jigga attended a pre-fight dinner at the hotel’s restaurant with Dame Dash, Kareem “Biggs” Burke and other members of the Roc-A-Fella Records team, Def Jam Recordings co-President Lyor Cohen and executive consultant Irv Gotti, DMX and the Ruff Ryders family, and Method Man. Ten days later the group would announce their 40-city “Hard Knock Life Tour” at a press conference in New York City. During their Sin City dinner meeting to finalize their road trip across North America, Jay had made it clear that his tour rider would require filet mignon and lobster, two bottles of Malibu rum, and a box of Cristal.

Jay-Z and Pamela Anderson, photographed during a party at the Studio 54 nightclub inside the MGM Grand hotel and casino in Las Vegas on January 16, 1999. Jigga is wearing a Roc-A-Fella Records leather jacket and an Iceberg Snoopy sweater.

18 months after this photograph was taken the actress would make a guest appearance in the rapper’s “Hey Papi” music video with her V.I.P. co-star Natalie Raitano; and with them both being in character for the shoot it seemingly outed him as a fan of the show.

The event was the official after-party for the earlier Mike Tyson vs. Francois Botha fight, which had been hosted in the hotel and casino’s Garden Arena. This bout was the return of Tyson to the ring after being banned for 15 months for biting Evander Holyfield’s ears in their June ’97 fight. Iron Mike won the match by knocking out Botha in the fifth round. This was a great outcome for the rapper too: as a fellow Brooklynite Jay was so devastated when a then-undefeated Tyson lost his 1990 fight to Buster Douglas in Tokyo he felt “physically hurt” himself.

Jigga attended a pre-fight dinner at the hotel’s restaurant with Dame Dash, Kareem “Biggs” Burke and other members of the Roc-A-Fella Records team, Def Jam Recordings co-President Lyor Cohen and executive consultant Irv Gotti, DMX and the Ruff Ryders family, and Method Man. Ten days later the group would announce their 40-city “Hard Knock Life Tour” at a press conference in New York City. During their Sin City dinner meeting to finalize their road trip across North America, Jay had made it clear that his tour rider would require filet mignon and lobster, two bottles of Malibu rum, and a box of Cristal.

Jay-Z, photographed at a party celebrating the launch of the latest Emporio Armani collection by event photographer Eric Weiss in New York City in October 1999. The rapper, who is wearing the first denim suit made by his own Rocawear brand, attended the event with his mentor Jaz-O.

The legendary Lauryn Hill hosted the party at the brand’s Madison Avenue store, which doubled as a charity event raising money for her non-profit Refugee Project. Armani had sponsored her “Miseducation World Tour” earlier that year and she spent much of her time in ’99 opening Armani boutiques and hosting brand events across the world to raise money to send underprivileged youth to Camp Hill in the Catskill Mountains; with the aim of enhancing campers’ cultural awareness and self-esteem.

Jay-Z, photographed wearing Michael Jordan’s “23” Chicago Bulls jersey during a Super Bowl XXXIII pre-party at a club in Miami Beach on January 30, 1999.

On the 28th Jigga and his Roc-A-Fella Records brethren had flown South on an American Airlines service leaving the LaGuardia Airport in Queens, taking up the majority of the first-class section on the plane. Never passing on a chance to put in work, while waiting in the airline’s lounge Jay would conduct a “warm, genial and generous” interview for an upcoming cover story for Vibe magazine with journalist Harry Allen. It was a busy time for the Roc-A-Fella co-CEO, having announced the record-breaking “Hard Knock Life Tour” during a press conference just two days earlier.

On the Saturday night before the Denver Broncos and the Atlanta Falcons vied for NFL supremacy, Hov was on-stage headlining the WEDR-99 Jamz radio station’s “Super Bowl Super Jam” at the Miami Arena in the heart of the city. The event was co-produced by Def Jam Recordings and brought a taste of New York to The Magic City with acts such as DMX, Foxy Brown, Method Man and Redman, Fat Joe, Cam’ron and Funkmaster Flex joining the Brooklyn rapper on the bill. Other performers included 112, Trick Daddy, 69 Boyz, Tyrese and TQ. LL Cool J and Brandy hosted the event, with a portion of the ticket proceeds going to several NFL-aligned charities.

On Sunday Jay and his Roc La Familia were part of 75,000 football fans inside the Pro Player Stadium watching as the defending champion Broncos defeat the Falcons 34-19.

Jay-Z and Paul “Mastermind” Parhar, photographed backstage after the sixth show of the “Hard Knock Life Tour” at the Air Canada Centre in Toronto on March 10, 1999. Jigga is wearing one of the early Rocawear hoodie samples.

That night the legendary Toronto radio DJ had hosted the concert, which featured classic performances from tour acts DJ Clue?, Method Man and Redman, DMX and headliner Jigga. Tickets for the show ranged from $25-$49 for the 11,000 fans in attendance. It was the first time the city had hosted a hip-hop concert of that magnitude. The 54-date tour was a critical and commercial success, grossing $18 million in ticket sales and suffered no cancellations, no artist drop-offs, or any incidents of violence. 

During his time backstage Mastermind was also involved in the Platinum and Gold plaques presentation for the acts by the tour’s supporting label Def Jam Recordings. Hov received a 4x Multi-Platinum plaque for Vol. 2… Hard Knock Life and a plaque commemorating “Can I Get A…” as his first top 20 single on the Billboard Hot 100. The plaque presentation was done in Toronto because it was the first time Def Jam executives were able to get the tour acts in the same room at the same time.

At the time Mastermind was working at the Energy 108 station in Canada’s most populous city, co-hosting “The Street Jam” with comedian Russell Peters. Mastermind had been working in the city as a radio DJ and programmer since 1987, and remembers first hearing of Jay-Z due to his work with his early rap mentor Jaz-O and later spinning his feature on Original Flavor’s “Can I Get Open?” in ’94.

Mastermind would meet Jaÿ-Z for the first time in New Orleans during a radio and DJ convention in July 1996. The Brooklyn rapper’s debut album Reasonable Doubt had recently released, and the whole Roc-A-Fella Records team were in the city to promote the album and its singles.

The Roc celebrated their various successes—including Reasonable Doubt debuting at number 23 on the Billboard 200 and the second single “Ain’t No Nigga” still receiving a lot of airplay and club attention—with a label dinner in a small restaurant on Bourbon Street in the city’s French Quarter. Mastermind was invited to attend the private dinner by one of the label’s executives, where he joined the team in popping unlimited bottles of Cristal champagne. Mastermind tells me every time they met Jay was “super kind” and “very gracious.” His favorite Hova tracks include “Murdergram,” “La La La (Excuse Me Miss Again),” “Where I’m From,” “So Ghetto,” “Streets Is Watching” and Friend Or Foe.”

Jay-Z, Magic Johnson, Dame Dash and Keith Sweat, photographed backstage after the “Hard Knock Life Tour” stop held at the Lakewood Amphitheatre in Atlanta on April 10, 1999.

Jigga was fresh off the stage after closing out the show performing “Money Ain’t a Thang” with Jermaine Dupri, with both wearing Atlanta Falcons jerseys. Earlier that day Jay, Beanie Sigel and Dame Dash had been spotted buying fresh pairs of fresh Air Force 1 sneakers at the Lenox Square Mall in Buckhead.

This photograph was organized and taken by David “Big Daddy” Clark, who was working for Def Jam Recordings at the time.

Jay-Z, Kendell Stoute and Tasha “Jane Blaze” Knight, photographed at the launch party for the first Rocawear clothing line, held at the Altman Building in New York City on July 28, 1999.

Jane Blaze attended the party with Kendell, who is Steve Stoute’s brother. Back in the mid-’90s Blaze used to frequent Maria Davis’ famous “Mad Wednesday” parties at Club E.S.S.O. in Manhattan; and when she saw a young Jaÿ-Z performing “22 Two’s” she knew she was witnessing the rise of a living legend. She was hooked by the lyricism, the confidence, and the genius behind his artistry.

The first time she would officially meet Hova was during the recording session of the remix of Ja Rule’s “Holla Holla,” where she found the courage to spit a freestyle for the Brooklyn rapper. Roc-A-Fella Records had been looking for some female acts to sign to label alongside Amil and her Major Coins group, and when Jay liked what he heard from Blaze he spoke of signing her to the family. However, she had recently signed a deal with Jive Records and didn’t want to burn bridges by pursuing an opportunity at the Roc. She did manage to secure a Memphis Bleek appearance on her 1999 single “Get With This” however. After that first meeting, every time that the two ran into each other on the scene Jay would remember her and show love and respect. This only served to add to her admiration for him.

There was a few hundred guests at the reception celebrating the Roc-A-Fella Records’ co-owners newest major business move. Roc Wear had first come to life in mid-1998 with a humble start in in the label’s offices at 17 John Street in Lower Manhattan. Three employees (who “didn’t really know how to sew”) were tasked with stitching the logo onto shirts and hats using second-hand machines that were well, well past their expiration date. Jigga and other Roc artists were soon seen sporting some of the preliminary designs, building hype for the label on the streets. Seeing the brand’s potential, Russell Simmons linked the Roc with industry veterans Alex Bize and Norton Cher, who helped source the infrastructure needed to mass-produce a complete line. As he famously rapped on “4 Da Fam,” eighteen months later the brand had achieved $80 million in retail sales; in just three years that number was a massive $500 million.

“First album niggas love me ’cause they thought I was poor
Guess I’m successful, industry don’t love me no more
Well, I’m the same nigga from your corner, bubblin’ raw, skully tilted, pants sagging damn near touching the floor
And I come with durags to your so-called awards, t-shirt with my chain out like fuck you all”

Jay-Z and red carpet host Rebecca Romijn, photograpged at the MTV Movie Awards, held at at the Barker Hanger in Santa Monica on June 5, 1999. Hov is wearing a Gucci suit, dress shirt and tie, and was later voted as one of the “Best Dressed” celebrities by television viewers.

Later that evening Jigga and Romijn together presented the award for “Best Action Sequence,” which was won by Armageddon. Hov’s Rush Hour-featured single “Can I Get A…” was nominated for “Best Song From A Movie,” but he lost the award to Armageddon’s “I Don’t Want To Miss A Thing” by Aerosmith. In a late-1998 interview with MTV News Jay had told the host that it was actually one of his favorite songs of ’98, explaining how “the emotion in that record was just crazy. To think about loving something that much, that you don’t want to go to sleep because if you dream of someone the sweetest dream would not be enough… That’s deep love. Either that or it’s obsession. I don’t know which one, it’s on the borderline right there. But imagine loving someone that much.” He posed that question to the interviewer, asking “Can you? Your eyes are getting wet. She’s in love right now [laughs]. I could never, but she can imagine that, you see?”

Jay-Z with fan Derek Lane, photographed at a meet and greet session after the twenty-seventh “Hard Knock Life Tour” show at the Rosemont Horizon arena in Rosemont, Illinois on April 4, 1999. During the show the rapper had worn Curtis Conway’s “80” Chicago Bears jersey.

In a review of the show for the Chicago Tribune, Joshua Klein wrote that Jay-Z had “almost single-handedly set some new standards at the Rosemont Horizon Sunday night” in his headlining set, having “the songs and swagger to go with the big pyrotechnics.”

Derek had been a fan of Hov for a few years, and he traveled to numerous cities during the tour to see his favorite rapper perform live and attend the meet and greet sessions. When they met Jigga was “super nice, cool, humble and down to earth.” Lane and his crew were able to hang around for a bit longer after this meet and greet session concluded, and Jay signed for him his event ticket, a copy of his Vol. 2… Hard Knock Life album, and the promotional placard hung by the table.

Shawn Carter’s young nephews LaVelle, Ramel, Jarrel and Colleek were accompanying him at points during the tour, along with Dame Dash and Kareem “Biggs” Burke’s sons. At one point Jay turned to the group of kids and asked them what they wanted for their dinner, listing off Italian, Japanese and numerous other cuisines.