Jay-Z and Amil Kahala Whitehead, photographed backstage during the “Hard Knock Life Tour” by Lenny Santiago in April 1999.  

Raised in all five New York boroughs with her parents passing down black, Cherokee and European heritage, Amil grew up in love with the hip-hop culture. “When The Fearless  Four and Run-DMC and all those groups came out I would go to the store and buy the albums and rap to the instrumentals,” Amil once recalled in an interview. “It was just something that was in me. I would just sit in my room and work on all of these rhymes.” When she was 12 she started rapping at local talent shows, and honed her skills in the cafeteria at school. She became a mother at a young age, and depended on welfare and small-time hustling to get by. 

Jigga would first meet Amil in April 1998 when she was a member of the all-female rap trio Major Coins, which she had joined a year earlier after meeting Liz Leite and Monique “Nicki” Smith. He had been wanting to include a strong female voice on his upcoming Rush Hour soundtrack single “Can I Get A…” and had brought them in to audition for the role. While Nicki was the original choice for the role, when Amil freestyled a verse for Jay he knew immediately she was the voice he needed. She was hesitant to appear on the track without her group, but was encouraged to do so by the Roc-A-Fella family as it would be a major look for the young rapper, and in-turn her group. “Can I Get A…” remains notable for popularizing both Amil and Ja Rule, as well as becoming one of Jay-Z’s most commercially successful singles at the time with it peaking at #19 on the Billboard Hot 100. Later that year Amil would sing the “Nigga What, Nigga Who (Originator 99)” chorus as her second contribution to Vol. 2… Hard Knock Life.

The Roc-A-Fella Records co-founders decided to sign Major Coins to the label, and at the May 1998 premiere of his musical film Streets is Watching Jigga had them walk the red carpet with him so he could introduce his “new girl group” to the media. Leite is the female voice heard on the chorus of Vol. 2′s “It’s Like That.” However, after not producing any notable work for the label, in 1999 Amil decided to pursue a solo career full-time and Major Coins disbanded. 

Amil was now known as the “First Lady of Roc-A-Fella Records” and the label went into promotional overdrive. “Jay just put this career in my hands,” she once said in an interview with Vibe magazine. “I went from having nothing at all to wearing diamonds.” She would appear on-stage during the record-breaking “Hard Knock Life Tour,” was set-up with a feature in a Sprite commercial, and contributed to “Pop 4 Roc,” “S. Carter” and the hit single “Do It Again (Put Ya Hands Up)” on Jigga’s fourth studio album Vol. 3… Life and Times of S. Carter. As well as contributing to tracks by Memphis Bleek, Rell and Beanie Sigel, Hov would also use his connections to get Amil guest appearances with Funkmaster Flex (“For My Thugs”), LL Cool J (“Hello”), AZ (“How Many Wanna”), Mariah Carey (the “I Still Believe” remix) and Tamar Braxton (“Get None”).

The year 2000 was another busy one for the First Lady of the Roc, with her opening up for Hov on tour around the world, being given her own imprint Major Coins, and contributing to classic Roc tracks such as “Hey Papi” and “You, Me, Him and Her.” She also gave up smoking marijuana and began a relationship with Wu-Tang affiliate Killah Priest (“They say he used to talk to this girl from Roc-A-Fella; well, why they never drop nothing together? They say she had a baby by him, but where’s that?”)

In the recording process since 1999, in September 2000 Amil would finally release her debut album A.M.I.L.: All Money Is Legal. “For a female in this game to write her own stuff is a big statement,” Amil said upon its release. “I hope that with All Money Is Legal, people will get the chance to hear what I have to say and the life that I’ve lived.” Jigga added to these sentiments, saying “she surprised me [on this]. Her album is gonna be the surprise of the year because she has such a talent for song-making.”

Producer Just Blaze has credited his work on Amil’s debut as raising his profile in the Roc-A-Fella camp, and getting him placement on The Dynasty: Roc La Familia. “Me and Amil got along really well,” Just Blaze recalled in a 2013 interview with HipHopWired. “My in [to the Roc] really was engineering Amil’s whole album. I recorded that entire album, engineer wise. Then I also co-produced and touched up a lot of the producer’s other beats.” When Jay-Z heard Blaze’s “That’s Right” beat it made him a believer in the up-and-coming beatsmith, as the producer explains here: “Jay wasn’t really messing with me for like the first year [after Gee Roberson introduced us]. Then I did this record with Amil and Bathgate called ‘That’s Right,’ and when Jay heard it he was like ‘Yo, I’m jumping on that, who did the beat?’ Once I did a record that he liked, then he was a little more receptive to my work.” 

While it featured three Jay-Z guest verses,the classic Roc posse cut “4 Da Fam,” and Beyoncé’s first-ever solo guest appearance on “I Got That” with an accompanying video directed by Hov himself, the album didn’t receive commercial success and got mixed reviews from fans and critics. The pressure was now on Amil to produce something—and the cracks started to show. 

After slowing down on promotion of her debut album and her single appearance on The Dynasty, Amil seemingly disappeared. Memphis Bleek once said that she simply stopped turning up for the Roc-A-Fella recording sessions at Baseline and music video shoots. One day Jay-Z informed the team he was ready to cut her loose, telling the Roc-A-Fella crew that “you’ll never hear from her again.” Her final appearance in a Roc-A-Fella Records project was her cameo in the early-2001-filmed State Property as Untouchable J’s assassin.

Jay addressed the situation on The Blueprint’s opening track “The Ruler’s Back” with a witty section playing on the stage names of his Roc-A-Fella artists: “There’s a lot of rappers out there trying to sound like Jay-Z; I’ll help you out, here’s what you do: You gonna need a wide lens cause that’s a ver’ big shoe; and you got a couple of Beans and you don’t have a Clue? Your situation is Bleek, I’ma keep it Rell, ‘cause fucking with me, you gotta drop Amil!”

In an interview with HipHopNews at the top of 2003, Amil spoke publicly for the first time on why she left Roc-A-Fella Records, saying that she “felt excluded” from label activities, and eventually lost her love for the team. She revealed that by the end of their relationship she would have to go through Jay’s assistant Carline Balan to talk to him because he wasn’t picking up her calls. She also felt the pressure from the poisonous rumors that had followed her over the past few years, such as she was working a day job at Kmart or that she was pregnant by a married man. 

Now a practicing Hebrew Israelite, in 2005 Amil emerged from retirement and temporarily re-formed Major Coins. The group released a few songs on the mixtape circuit, including the single “Glamorous Life” which was featured in MTV’s Mixtape Monday series. She disappeared again until 2008, when she released two mixtapes entitled Az Iz and Amil Returns: The Lost Classics Edition.

One of the misogynistic rumors surrounding Amil’s departure from the label was that she was let go because she had put on weight because of “laziness” or pregnancy. In a 2006 interview, when asked whether female MCs are forced to meet standards that male counterparts are not, she reasoned that they “definitely do. You have to be picture-perfect and you have to meet the standards of the perfect woman. That’s unreal to me. Real women do not have plastic-looking bodies. The average woman is not a size 0. You can do crazy things to keep yourself looking like that, or you could just be you. Me, I choose to just be me.“ 

In August 2011 she was forced to give an exclusive interview to Vibe magazine when a fake Twitter page was created under her name and began to slander everyone from Foxy Brown to Rick Ross to J. Cole. In the interview she revealed that she hadn’t “spoken to Jay in years, but I really wish I could talk to him because that would just really bring closure to me. But he knows I love him. People think there was bad blood between us, but there never was any bad blood. Things happened and I wasn’t ready for where my career was going at that time. It was really overwhelming.”

As part of its “Ladies First: 31 Female Rappers Who Changed Hip-Hop” series, Billboard connected with Amil in 2014 and manged to acquire the most in-depth answers as to what led her to leave the rap game back in 2001. “I didn’t put my all into it. I felt like it just wasn’t for me,” she solemnly explained. “I started rebelling because I wanted out. It was easier for me to slip away. I faded myself. No one faded me. I think [Roc-A-Fella] knew through my actions that I wasn’t in it. I wasn’t putting any effort into promotion. I wasn’t looking at it as a career.”  Amil has also revealed her young son’s poor health guided her choice: “At the time my son Pape’s asthma, who was 8-years-old at the time, was getting worse and no one was there for him. I had to be there for him.”

Regretting her choice to pursue a solo career, Amil revealed she “was fine being an around the way rapper. If I could go back in time and do it all over again, I wouldn’t have allowed myself to jump in the game.  If I would have did it again, I would have left it alone. I wasn’t cut out for it. I probably would have stepped in as a writer.” She also revealed she made poor choices with her money and commitments, saying “I didn’t think about the legalities of a lot of things. I never cared about the contracts. I could have been signing my life away… I was not a businesswoman at that time. I didn’t have a manager or the things that most artists have.”

As far as her interactions with Jay-Z at the time of her departure from the label, she explained that “there was never a conversation about me leaving. Jay just knew that that’s not where I wanted to be. I had told him before that I couldn’t do it for another year. I think he understood, overall. He thought that as time went on I’d be ready, but later realized I wasn’t. I know he knew, ‘She don’t give a fuck about this shit.’ I was fine being an around-the-way rapper. If I could go back in time and do it all over again, I wouldn’t have allowed myself to jump in the game.” 

Despite the rumors that surrounded her sudden departure, Amil has insisted that her and Hov were never romantically involved: “Whenever me and Jay recorded it was a natural thing. It was always smooth. The way we sounded together, it was a good chemistry. Jay had respect for my talent—writing and my voice—nothing more. Jay gave me the opportunity of a lifetime, and what I did with it was my own decision. That was my brother. There was never a relationship between me and Jay or anyone over there. He was like a brother. He was very protective over [me]. I’m never going to lose any love for Jay.” 

In March 2014 Amil resurfaced once again, and released a new single titled “Remember”—which sampled Jigga’s “Where I’m From” and the refrain from Faith Evans’ “You Used To Love Me.” She had plans to release a ‘90s-inspired mixtape A Moment In Life, but it remains unreleased. Her sister has informed me that she is doing well and enjoying life out of the spotlight.