1999 was a phenomenal year for hip hop star Eve. That year, the young rapper from from the City of Brotherly Love became the first woman to signed to Ruff Ryders, a hip hop label that was known for having a roster of hardcore MCs who were also stars, like DMX and The Lox. The signing was a match made in heaven: like DMX, Eve was a bit more aggressive and gritty than her peers, yet achieved the same success, or sometimes more. Ruff Ryders tried not to pressure her to conform to the norm and allowed her to feel comfortable being her normal self in the spotlight, and Eve went on to have a spectacular year for a rookie who just got drafted into the league.

Luckily for Eve, she came out at a time where women in hip-hop could achieve success without just flaunting sex appeal. From 1996 to 1999 there was success for a variety of women in rap. You could be the baddest jawn from around the way like Lil Kim, Foxy Brown, and Trina. You could be an Afro centric jawn and win big at the Grammys like Lauryn Hill. You could even be the big jawn who is funny with a creative side that is out of this world, like Missy Elliot.

Eve could rap with the best of them, and had sex appeal, but that didn’t overshadow her lyrics, and was hardcore like one of her famous peers: the late Gangsta Boo. Like her peers, she had a sharp tongue but had that dog in her, which happened to be a pitbull. So when it was time for the illest pitbull in a skirt to come off the bench in 1999, she began to a name for herself like rookie Steve Francis or Elton Brand.

Ruff Ryders - What Ya Want (Official Music Video) ft. Eve, Nokio

Eve’s rookie season was crazy. Of the three singles off her debut album Let There Be Eve…Ruff Ryders’ First Lady — “What Ya Want,” “Gotta Man,” and “Love Is Blind” — all became hits and had memorable B-side cuts such as “Maniac,” and “Philly Philly,” featuring the Broad Street Bully, Beanie Sigel, that made their way into a Cosmic Kev’s set list on Power 99 FM.

It was a road to get there, though. In the years before her debut, Eve found herself featured on classic street bangers like Missy’s “Hot Boyz remix” and The Lox’s “Ryde or Die Bitch,” as well as a timeless hit that went on to win a Grammy (The Roots’ “You Got Me”). She had rapped on beats produced by heavy hitters such as Swizz Beats and Timbaland, held her own on tracks with elite wordsmiths like Black Thought, DMX, Beanie Sigel, Nas, Jadakiss and even had a legend like Prince hit her up to be featured on his album. Then at the end of the third quarter of 1999 she dropped Let There Be Eve…Ruff Ryders’ First Lady and became the third female rapper to debut number one on the Billboard 200. Eve was putting up numbers on the charts her rookie season, and probably averaged a double double. But what made Eve stand out to me was her third single “Love Is Blind,” which showed the horrific cons of being the bad chick who dated the street dudes who were making money.

Eve - Love Is Blind (live)

Sometimes, the hip-hop industry (especially the hip-hop industry of 25 years ago) doesn’t make space for women who don’t fit into an easy lane. What about when they want to make songs about feeling insecure because men only want them for looks and nothing more? What about the dangers of a woman working in the clubs or dating men with street occupations? “Love is Blind” to me is the closest thing that shows that side of the game.

During Ruff Ryders documentary on BET, Eve stated that the song was originally a poem she wrote when she was 16 about a friend of hers who was dating a 35-year-old who beat her. The lyrics were mixed with empathy for her beloved friend and rage for the manipulative monster who was the source of her pain. Even with those emotions, Eve also dropped lines that held her friend accountable for her choices: “I mean, shit, he bought you things and gave you diamond rings / But them things wasn’t worth none of the pain that he brings / And you stayed, what made you fall for him? / That n—– had the power to make you crawl for him.”

Even in her song “Heaven Only Knows” she converses with the woman in the mirror about her past ways with lines like “Thought it was cute to flirt with older cats up in they face / Didn’t have a daddy so I put a daddy in his place.” With all the accomplishments that Eve made during her first year as a rap star, to have a conscious hip hop song about a woman poetically documenting the abuse that her friend was going through that went on to sit well on the charts and later to be held as a classic hip hop song, is my personal favorite highlight moment of her rookie season.

Eve - Gotta Man

25 years later Eve went on to become a well respected hip-hop veteran, a Grammy award winning music artist, and even became a star in Hollywood. This year, she announced her autobiography Who’s That Girl, which is going to give us more insight on her first year as a rap star as well as some other experiences the public may not have been aware of.

The book comes out on September 14th — the 25th anniversary of Let There Be Eve — and she’ll be returning to her hometown later that week for a book tour and discussion in conjunction with Uncle Bobbie’s Coffee & Books in Germantown. The event takes place on Wednesday, September 18th, at Enon Tabernacle Baptist Church in the Stenton neighborhood of Northwest Philadelphia. Tickets are available here, pre-order Who’s That Girl now here.