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 and Jay Electronica, photographed onstage at the 10th annual Brooklyn Hip-Hop Festival by Crook Robbins on July 12, 2014.

At this moment the Roc Nation co-founder and figurehead was giving one of the label’s most talented artists the Five-Percent Chain he had commissioned a year earlier. Jay Elec would later offer it to Rapsody during a show, but once they got backstage she respectfully gave it back to Elec due to not being a practicing member of the Nation.

During the week-long promotional run for Magna Carta… Holy Grail the Brooklyn MC had worn a similar chain, which actually belonged to NBA star Carmelo Anthony. He had seen his friend wearing the medallion at a party and “stole” it from around his neck. While not an active member of the movement, Jay loved wearing the piece so much he commissioned his personal jeweler Alex Todd to make his own diamond-encrusted and yellow gold version of the Five-Percent Nation emblem. After wearing his joint throughout ’14 while facing misplaced media scrutiny, he took the opportunity to chain his little brother à la the tradition of Roc-A-Fella Records in the ’90s and 2000s.

The Five Percent Nation of Gods and Earths was founded in 1964 by Clarence 13X or “Allah the Father.” Allah was a former Malcolm X follower who believed that 85% of the world’s people are blind to knowledge of themselves and God, while 10%—including those in government and the media—are committed to keeping the rest ignorant. The remaining 5% (hence the movement’s name) are thought to be Poor Righteous Teachers whose understanding of a “Supreme Alphabet,” “Supreme Mathematics” and “120 Lessons” equip them to educate and liberate the masses. The first verse of MCHG’s “Heaven” features Hov referencing the 5% teachings he had been receiving at the time, namely the meaning of the ALLAH acronym and the Twelve Jewels. While you could align his relationship with Electronica and his higher NOI references, he has been referencing the teachings of the movement since he was in The Originators with Jaz-O and jewels are scattered throughout Reasonable Doubt.

JAY Z, photographed as he walked from his Escalade to the stage at the 10th annual Brooklyn Hip-Hop Festival by Xavier W. on July 12, 2014.

Hov made an appearance at the festival to support his Roc Nation comrade Jay Electronica. He surprised the crowd by walking out to his remix of Big Daddy Kane’s “Young Gifted and Black,” supported by his little brother. This segued into “We Made It,” the Soulja Boy remix that Z and E had released earlier that year, then their 2010 classic “Shiny Suit Theory,” and finally a solo performance of “Public Service Announcement.” “Peace and love Brooklyn! It feels good to be home,” Hov exclaimed, beaming down at his hometown crowd from the stage. At the end of his set he took off his Alex Todd-crafted Five-Percent Nation chain and hung it around Electronica’s neck. During the Magna Carta… Holy Grail promotional run he had borrowed a version of the chain from Carmelo Anthony; and he loved it so much he commissioned the making of his own piece. Jay Elec would later offer it to Rapsody, but she passed due to not being a practicing member of the Nation.

After his much-appreciated appearance Hov headed straight for a nearby helipad to board a helicopter to fly to MetLife Stadium in East Rutherford, New Jersey to avoid getting caught in traffic—as he was due to perform at the second of two “On the Run Tour” shows at the venue with his wife Beyoncé. Over the two nights the couple impressed 90,000 fans and grossed nearly $12 million in ticket sales.

Jay-Z, photographed for his feature in the December issue of Vibe magazine by Vincent Skeltis in 2000.

The rap mogul is wearing a black leather logo jacket, a black crewneck sweater, a white cotton crewneck t-shirt and a black ribbed singlet as a durag—all of which were produced by Rocawear, his own label which had recently netted $80 million in sales after just one year on the market. His diamond and platinum Rocawear chain and earrings were made by Jacob the Jeweler.

The magazine covered Jigga as the flagship artist of Roc-A-Fella Records family, and had individual features on his up-next crew Memphis Bleek, Beanie Sigel and Amil.

Thought he lacked formal training, Skeltis began his photography career as an assistant to the famed David LaChapelle. While shooting the King of Rap was a great opportunity for the young shooter from New Jersey, Skeltis has said that after paying the production costs such as film and processing and the stylist and assistant fees, he barely broke even from the shoot.

This cover image and those inside were digitally retouched by Jack Mihkel Prenda.

Jay-Z, Memphis Bleek, Amil and Beanie Sigel, photographed on the set of the music video for the classic Roc-A-Fella Records posse cut “4 Da Fam” by Lenny Santiago on July 28, 2000. The music video was shot in a production studio in Hollywood and directed by Nick Quested, who told me that production went smoothly and everyone was a consummate professional on-set.

The second single from the First Lady of the Roc’s debut album All Money is Legal, “4 Da Fam” was released to radio and stores on September 13, 2000. It was the second time the four Roc representers had got together on a track, and for fans and critics worldwide it was heard to be substantially better than Vol. 3’s “Pop 4 Roc” effort. “4 Da Fam” peaked at #29 on Billboard’s “Hot Rap Singles” and spent 11 weeks on the charts. In a hugely successful year for the co-CEO of the independent label this was an intentional move to keep the rest of Roc La Familia bubbling in the street.

The track was produced by Queens native Tyrone “Ty” Fyffe, who learned his producing craft from Teddy Riley during the New Jack Swing era. His first production placement was the classic “Rump Shaker” by Wreckx-N-Effect, which also features Pharrell Williams’ first writing credit. During his time with Teddy Ty was blessed to meet Michael Jackson at Neverland and watch the master at work. By the end of the ’90s Ty had returned to New York, was taught further by Erick Sermon of EPMD, and was a regular feature at D&D Studios and the early days of Baseline. He has production credits on Roc-A-Fella releases such as Jigga’s Top 5 effort “This Life Forever,” the heavy “Murdergram” by Murder Inc., Beanie Sigel’s “Change” and six tracks on Cam’ron’s Come Home with Me album.

Ty Fyffe’s majestic beat sampled Roy Budd’s theme-song from the 1972 action film Fear is the Key. He produced it specifically for Jigga with the rapper in the room, taking inspiration from his hard-hitting, grimey output of ’99. However, at that point in time the Roc-A-Fella team were focused on raising the profile of his understudies and Dame Dash bought the beat for Amil’s debut, much to Fyffe’s disappointment. That evening Ty watched as Bleek went into the booth and blacked out; and when Beans heard his efforts he accepted the challenge and jumped on. A 22-year-old Justin “Just Blaze” Smith happened to be hanging around Baseline that day and he assisted Ty by stepping in as recording engineer. A few weeks later Ty was visiting the Def Jam Recordings offices in Midtown Manhattan and he saw Hov and Kevin Liles riding the escalator up. The Brooklyn MC leaned down, called out “You know I had to get on that joint, right?” and kept moving.

It was a busy week for the Roc-A-Fella team that July, as the videos for “4 Da Fam,” “Change The Game,” “Do My…,” “Hey Papi,” and “Is That Yo Chick?” were all shot across California over the course of just five days. The Roc made the Four Seasons in Beverly Hills their home base while on the West Coast, but they hardly slept—there was the Nutty Professor II: The Klumps premiere to attend, multiple club appearances, and Jay spent many late nights in the hotel bar speaking with journalist kris ex for a feature on the Roc-A-Fella Four in the December issue of VIBE magazine.

In that interview the Brooklyn MC cleared up speculation around one of the most noticeable lines of his “4 Da Fam” verse: “I’m having a child, which is more frightening.” While Jay had often mentioned being a father figure to his nephews, this reference to his impending fatherhood would be, until Beyoncé’s pregnancy and the birth of Blue Ivy, one of only two references he made on wax to having a child of his own.

In the Summer of ’97 Jay had begun dating actress Rosario Dawson, and some say that their three-year relationship ended soon after she suffered a miscarriage. This, from a Vibe magazine interview conducted on the set of “I Just Wanna Love U (Give it 2 Me)” in November 2000: “Yes, he did have a child on the way as he rapped on Amil’s ‘4 Da Fam,’ but he stops short of giving a reason why that’s no longer the case.” In April 2003, nearly three years later, he would revisit this time in his life in an interview with Playboy magazine, explaining: “The girl I was seeing about four years ago had a miscarriage. But I wasn’t sad. I didn’t even grieve. Maybe it happened because I wasn’t ready to be a dad.”

His other early reference to fatherhood was on “This Can’t Be Life,” where he talks about an unnamed girlfriend suffering a miscarriage. As the track was recorded shortly after “4 Da Fam” many assume it was a reference to the same pregnancy. However, in Decoded Jay explained that the miscarriage he was referencing took place in 1994—the year he set his “TCBL” verse. “This refers to something that happened to me around that time, 1994, when my girl of five years got pregnant and lost the baby in a miscarriage. Now, obviously, miscarriages happen everywhere, to anyone, but the point is that on top of the especially acute paranoia and disappointment and exhaustion I’m feeling from the street life, friends getting shot, your family being broke, I have to deal with the everyday tragedies that stalk everyone. And when that hits you, sometimes it becomes clear that you have to get out, that this really can’t be life, it has to be more.” 

The ex-girlfriend referred to is Stephanie, who he met in Virginia when he was in the state drug running. They dated for five years from 1991-1996, with Hov living between her home in Virginia and his apartment at 560 State Street in Brooklyn. Their relationship and the stress his early rap career put on it inspired “Song Cry.”

Jay-Z, Busta Rhymes and Joseph “JoJo” Pellegrino, photographed during an early screening of the Roc-A-Fella Films production State Property at a screening room in Lower Manhattan, New York City in December 2001.

This photograph was taken by Gabe Tesoriero, who currently serves as the Executive Vice-President of Media and Artist Relations at Def Jam Recordings. During his years working for Roc-A-Fella Records he built a close relationship with Kanye West, and helped him realize his College Dropout dreams with the label. He has been working as ‘Ye’s publicist since 2003.

At the beginning of ’01 Jay heard from a Brooklyn associate of his that a Staten Island native and Wu-Tang Clan affiliate was in the city recording his own version of “Where I’m From” at Briel Studios. Jay pulled up on the session and ended up being impressed with Pellegrino’s rhymes, telling him “my man, you are money in the bank.” The Roc-A-Fella co-CEO helped make sure DJ Clue received a copy of the single to play on his “Battle Of The Streets” segment on his Hot 97 radio show, which JoJo’s single would win three nights in a row and then be awarded inclusion on the next Clue tape.

During the session Jay had asked and found out the Italian MC was signed with Chris Lighty’s Violator and Loud Records; then seemingly hinted at this being a mistake because the Roc would have been interested in him if they knew he was a free agent. JoJo would be invited to record his debut album Pellegrino Story at Baseline Studios, with Busta, Method Man and Kurupt stopping by to record verses for the album. Unfortunately the deal with Violator went south so the album was shelved, and “The Rap Tony Soprano” was forced to leak the majority of the album to the streets to try secure another deal.

In October 2001 a freestyle by Pellegrino was included on the “Game Radio FM” station in Grand Theft Auto III through his connection with the Game Recordings label, reigniting interest in the Shaolin spitter. However he couldn’t secure a deal and was forced to continue as an independent artist. He has steadily released mixtapes since 2002, and earlier last year he released the stand-out “Shootaz” with Griselda’s Conway the Machine.

Jay-Z and Memphis Bleek, photographed as they walked the red carpet at the premiere of Eddie Murphy’s Nutty Professor II: The Klumps film, held at the Universal Amphitheatre in Universal City, California on July 24, 2000.

During his walk down the red carpet the Roc-A-Fella Records co-founder ran into Tamera Mowry, who was immediately starstruck. “I met him, it’s so weird. My sister Tia and I were at a premiere of Nutty Professor and he walked by and I was like, ‘Oh my god, that’s Jay-Z,’” she once told her co-hosts on The Real. “When I met him, you do get hit with the charm. But I found myself, strangely, asking for gum. I was like, ‘Can I have some gum?’” As an avid gum chewer, Jay happily obliged and shared a piece with the young actor. 

Back in June 1996 Def Jam Recordings had given a bubbling Jaÿ-Z one of his early breaks by including his Foxy Brown-featuring single “Ain’t No Nigga” on the soundtrack to the first Nutty Professor film. Four years later Jigga was now firmly at the top of the rap world, and he returned the favor by recording “Hey Papi” for the sequel, bringing his protégé Bleek and Amil along for the ride. Over a Timbaland beat Hov revealed a new growth in himself, announcing he was “off that player shit” and taking back his “Do It Again (Put Ya Hands Up)” promise to kick a woman out of his house just 15 minutes after inviting her inside.

Was this new outlook on account of his March ’00 meeting with Beyoncé? On “713” the husband of the Queen expressed that they time they spent together that month at MTV’s “Spring Break” festival in Cancun, Mexico had solidified to him that she was someone he needed in his life. At the time he was known worldwide for his “Big Pimpin’” mantra, so he may have returned to Baseline with the realization that his lyrics needed to be slightly altered to gain her sustained attention.

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.