The Startling Evolution Of Lil’ Kim

Kimberly Denise Jones, more famously known as Lil’ Kim, is one of the original American female hip hop stars. The Brooklyn native emerged on the scene in the early 1990s and started performing for Christopher Wallace (The Notorious B.I.G). Kim was eccentric, original, and very talented. We’re going to take a look at how drastically she has changed through the years.

Watch Her Shocking Transformation Unfold

Watch Her Shocking Transformation Unfold

Lil’ Kim has progressed from a fresh-faced musical novice to one of the most recognizable talents in the business. She has sold over 15 million records worldwide and continues to record actively to this day. However, changes in her appearance and personal life seemingly happened overnight and shocked the hip hop community. Here’s what happened.

1994 – Starting Out

Lil’ Kim had her early beginnings on the East Coast of the United States. She was born and raised in Brooklyn, and for a while spent time living on the streets. It was during her teenage years that she met Biggie Smalls (The Notorious B.I.G.), the man who would go on to have a major influence in her life.

1994 – Starting Out

In 1994, Smalls founded and promoted the New York-based rap group Junior M.A.F.I.A., which Lil’ Kim was a member of. They released just one record that received modest sales, and the group disbanded. Kim, however, was heading for much bigger and brighter things.

1994 – A Less Than Glamorous Retail Job

Lil’ Kim wasn’t always the sexy, sassy rapper we know today, but she was always somewhat of a fashionista. Before she met Biggie, Kim was just like any of us — she had a less than glamorous job at the department store Bloomingdales.

1994 – A Less Than Glamorous Retail Job

“We lived on the same block in Brooklyn,” she told BMI about Biggie Smalls. “I always thought he was cute, and when I first started talking to him, I felt like I’d known him for years. I was working at Bloomingdales, and friends of mine said to him, ‘You know, Kim knows how to rap.’ He was like, ‘Please! She’s too cute to know how to rap’.”

1994 – Early Relationship

When she was still a teenager, Lil’ Kim began dating a guy named Shawn Powell. The two apparently met while roller skating and began a pretty intense relationship. They had only been dating a few months when Powell was arrested. He committed armed robbery and received a prison sentence of more than eight years.

1994 – Early Relationship

While Powell was incarcerated, the couple continued their relationship and wrote lots of letters to one another. However, it was around this time that Kim began to associate with Biggie Smalls and realized that her hip-hop career had to come first. So she broke off her engagement with Powell. Not long after she started dating Smalls.

1995 – Junior M.A.F.I.A.’s Conspiracy

From working at Bloomingdales to meeting Biggie Smalls, in 1995, Lil’ Kim would release her debut album with the rap group Junior M.A.F.I.A. Conspiracy was released in the summer of ’95 and saw Billboard chart success (though critics had mixed reviews).

1995 – Junior M.A.F.I.A.’s Conspiracy

Conspiracy sold 69,000 copies in the first week landing it the number eight spot on the Billboard 200. Kim rapped on five of the 15 tracks alongside Faith Evans, Biggie, Trife and Larceny of The Snakes, Chico Del Vec, Kleptomaniac, Capone and Bugsy. Though the record is out of print, it was certified gold by the RIAA.

1995 – Career Progression

1995 was the year Lil’ Kim really started to make inroads in the rap game. Her personal and working relationship with Smalls was doing wonders for her career. She started out rapping for Biggie at some of his shows, and then, in late ’95 went into the studio.

1995 – Career Progression

Kim was preparing to start the recordings for what would become her debut album – “Hard Core”. Recording sessions began under the supervision of Smalls, and his close friend Sean ‘Puff Daddy’ Combs. The record was released the following year and has been considered groundbreaking in the history of hip-hop, opening more doors for female rappers.

1995 – Kim and Biggie

During this time Lil’ Kim also entered into an on-again-off-again relationship with Biggie Smalls. It’s unclear how much this impacted on the working relationships of Junior M.A.F.I.A., but it can’t have been easy for the other members of the group.

1995 – Kim and Biggie

Their tumultuous and tempestuous relationship continued up until Smalls’ murder in 1997. But, when they started out things were much happier for the both of them. They seemed to genuinely have a lot of affection for one another, and Smalls is thought to have called her just a few days before his death to tell her he loved her.

1996 – The Queen Bee Has Landed

1996 was a big year for Lil’ Kim, and it catapulted her into the limelight. First of all, her debut record, “Hard Core”, was released to universal critical acclaim. The album was certified as double platinum by the RIAA, and she released three singles, all of which were hugely successful.

1996 – The Queen Bee Has Landed

“Hard Core” contained extensive profanity and adult references, it is also considered one of the classic albums of hip hop. It was a controversial album, with a risqué cover, and this helped it perform very well. Lil’ Kim had well and truly landed as the new Queen of the hip hop world.

1996 – Hard Core Was A Success Before It Even Launched

In 1996, Lil’ Kim wasn’t the powerful solo artist we know today, but she was on the brink of something amazing. Even before Hard Core was released, her singles were destined for success because of the sheer star power on the recordings. Lil’ Kim’s debut albumfeatured artists like Left Eye, Miss Elliot, The Notorious B.I.G, and Puff Daddy which helped launch her into the spotlight.

1996 – Hard Core Was A Success Before It Even Launched

Lil’ Kim’s “No Time”peaked at number 18 on the U.S. Billboard Hot 100 and landed the number one spot on the rap charts — something that was so unusual for a woman. The single “Not Tonight” peaked at number six.

1996 – Arrest

1996 – Arrest

But it wasn’t all sunshine and rainbows for Lil’ Kim in 1996. She released her first album as a solo artist, but she also had her first high-profile arrest as well. This was apparently due to marijuana possession and would prove to be the first of several occasions in which Kim would make headlines for the wrong reasons.

You can see from the picture that she looks pretty angry about the situation. Few people look good in a mugshot, and no one wants their mugshot spread around the press. But the problem with being a successful recording artist is that your arrest becomes a big story.

1996 – Style Icon

Lil’ Kim was breaking boundaries when she burst onto the scene, and that was pretty clear to see even from an early stage. She has become something of a style icon over the years, and this likely all started from a very specific place. It can be traced back to ‘that’ promo shoot.

1996 – Style Icon

The album cover for “Hard Core” seemed fairly tame, Kim straddling a bear skin rug. However, the promotional shot for the album featured a much raunchier picture, the one above. It’s this kind of daring and style that helped to set Lil’ Kim aside from many of her contemporaries and turn her into a fashion icon.

1996 – Lil’ Kim Releases Her First Music Video

In 1996, Lil’ Kim was poised to take over rap music. After a couple of years of hard work, she finally released her first ever music video for the song “Crush on You” from her debut album Hard Core. The song featured verses by fellow Junior M.A.F.I.A. members Lil’ Cease and the Notorious B.I.G.

1996 – Lil’ Kim Releases Her First Music Video

“Crush on You” was an absolute success and peaked at number one on the U.S. Rap Chart. The music video featured a number of stars including Luther Campbell, Aaliyah and Sheek Louch of The Lox. It was the first appearance of Kim’s famous multi-colored wigs and featured her rocking bright green, blue, yellow and red locks.

1997 – Junior M.A.F.I.A. Call It Quits

Despite Junior M.A.F.I.A.’s modest success, the crew became defunct in 1997 after the tragic death of the Notorious B.I.G. Biggie was planning to retire from rap music anyway, stating in a 1995 interview (which was published in 2003 by XXL Magazine) that he planned to go behind the scenes and manage the careers of his Junior M.A.F.I.A. bandmates (this includes the career of Lil’ Kim).

1997 – Junior M.A.F.I.A. Call It Quits

Biggie’s death was too much for many of the members to handle, and the group disbanded. In 2005, three of the members (not including Lil’ Kim) released an album under the Junior M.A.F.I.A. name which didn’t match their previous success.

1997 – Lil’ Kim Goes On Her First Tour

In 1997, Lil’ Kim went out on her first ever tour. The No Way Out Tour was Puff Daddy’s epic headliner, but he managed to bring along some chart-topping hip hop acts including Lil’ Kim and Jay-Z. The tour was unusual in the fact that many hip-hop acts couldn’t afford the insurance required to tour after hip hop shows became (unfairly) known for violence and property destruction. This was one of the few tours that brought together a myriad of amazing artists to arenas across the country.

1997 – Lil’ Kim Goes On Her First Tour

Unfortunately, not all was well and good on the No Way Out Tour. Jay-Z managed to ironically find a way out when he quit. He resigned as the opening act after their December show in Madison Square Garden citing unfair treatment by tour promoters, technical difficulties, and sets cut short.

1998 – Hitting the Red Carpet

By the time 1998 rolled around, Kim was cementing her status as a massive star in the music world. She had enjoyed a successful debut album, and embarked on a wildly successful world tour with Puff Daddy (now P Diddy). And she was starting to enjoy the softer side of fame – the red carpet.

1998 – Hitting the Red Carpet

Kim attended many premieres and awards ceremonies and was on the receiving end of plenty of nominations. You can see her here at the 1998 Soul Train Lady of Soul Awards. This wonderful outfit shows how she is much more comfortable with her style and not afraid to be different. Gaga has nothing on Kim!

1998 – Launching a Label

Kim spent most of the late 1990s keeping herself busy with her career. After the tragedy in her personal life, throwing herself into work became a great outlet for the young rapper. And she made the decision in ‘98 to launch her own label, Queen Bee Entertainment.

1998 – Launching a Label

The label is still active now, and she set it up with help from Puff Daddy. The label included all the Junior M.A.F.I.A. members, as well as other talented artists that Lil’ Kim signed. The creation of the label further helped to facilitate Kim’s journey towards super-stardom and showed good business acumen as well.

1998 – Grieving

1998 might have been a good time for Kim in a professional capacity, but less so in a personal one. She had lost her mentor and former lover, Biggie Smalls when he was murdered the year before in 1997. The death shocked the rap world, and Lil’ Kim, understandably, took the news hard.

1998 – Grieving

She wasn’t known to have any serious relationships in ‘98, and that’s likely to do with her getting over the death. You can see from this picture how hard she took the death, as Mary J. Blige consoles her after the funeral. Kim’s personal life took a big hit, and some would argue she’s never fully recovered.

1999 – Lil’ Kim’s Iconic VMA’s Look

After the death of her lover Biggie Smalls, Lil’ Kim kept a low profile – that is, until she graced the red carpet at MTV’s Video Music Awards in 1999. The rapper showed up in what’s arguably one of the most iconic red carpet outfits of all time.

1999 – Lil’ Kim’s Iconic VMA’s Look

The rapper’s pastel purple onesie was designed by her stylist Misa Hylton and scandalously revealed one of her breasts. A purple wig and sparkly Steve Madden platforms finished the unforgettable look, which Diana Ross later tested when she jiggled Kim’s exposed breast during the awards show. The look was so iconic that Miley Cyrus recreated it for Halloween over a decade later.

1999 – She’s All That

In 1999, Lil’ Kim was only really known for her rapping, but she took a brief detour into the world of Hollywood. Kim played a role in the 1999 teen romantic comedy She’s All That. The film featured ’90s heartthrobs Freddy Prinze Jr. and Rachael Leigh Cook, and the script was a modern adaptation of the 1965 film My Fair Lady.

1999 – She’s All That

Lil’ Kim was cast as Alex Sawyer, one of the cool kids, though she didn’t have very many lines. The film also cast another hip hop star — Usher had a cameo as the campus DJ, though his character didn’t have a name.

She’s All That was so popular it reached number one in the box office and was another checkmark on Lil’ Kim’s long list of successes.

2000 – The Notorious K.I.M.

Many artists produce their best work in times of great loss or anguish. And, in 2000, Lil’ Kim released “The Notorious K.I.M.”, her second album. It was the first record since the death of Biggie, and the album is an obvious tribute. The new album also went platinum and has sold millions worldwide.

2000 – The Notorious K.I.M.

Kim’s memorial to her late beau is clear throughout the album. Many critics cited it as her best work, while others pointed out that the absence of Biggie’s involvement was notable. Nevertheless, this is an album it seems Kim had to make, as much for catharsis as anything else.

2000 – “How Many Licks?” Music Video

Lil’ Kim’s second studio album The Notorious K.I.M. wasn’t quite the success of her first. The single “How Many Licks?” was only able to reach number 75 on the Billboard Hot 100. However, the music video was a source of much controversy and further cemented Kim’s sexy, risqué image in the minds of America.

2000 – “How Many Licks?” Music Video

The video was directed by Francis Lawrence and follows the story of Kim, who releases a line of edible dolls that look just like her. These dolls are supposed to be used for men to practice certain intimate acts. The entire song is an illusion to the 1970’s Tootsie Pop slogan that says “How many licks does it take to get to the Tootsie Roll center of a Tootsie Pop.”

2000 – Cut From Her First Hollywood Film

The hysterical slasher movie satire Scary Movie is pretty much a staple when it comes to early-00s American comedies. What most people don’t know is that Lil’ Kim had a role but was cut from the film.

2000 – Cut From Her First Hollywood Film

Lil’ Kim was considered for the role of Brenda Meeks, who is a reoccurring character in the franchise and appears in Scary Movie, Scary Movie 2, Scary Movie 3 and Scary Movie 4. The character’s nickname “Brandy” comes from the name of actress she’s meant to parody. Who better to parody Brandy than Lil’ Kim? Unfortunately, at the last minute, producers went with Regina Hall for the role instead. We’re sure Queen Bee didn’t sweat it, as she had a budding rap career and was moments away from her first ever number one single.

2000 – More Daring Outfits

The turn of the millennium also marked a significant change in style and look for the young rap star. Her face looks largely the same, but she made definite changes to her hair. Here, we see a picture from the MTV VMA Awards, showcasing how to nail curly hair with blonde streaks!

2000 – More Daring Outfits

Kim also continued with more daring outfits, something she has developed quite the reputation for. This MTV photo is a good example of the kinds of outrageously awesome outfits Kim was wearing around this time. They helped her showcase her new style and maintain that bold approach that made her famous.

2001 – Lil’ Kim Gets Her First Number One Single

In 2001, Lil’ Kim broke records. She became the first ever solo female rapper to have a number one single on the Billboard Hot 100. The song was a cover of the 1974 Labelle hit “Lady Marmalade.” Rap’s Queen Bee sang alongside Christina Aguilera, Mya and Pink, and the song was so successful that it remained on the charts for five weeks.

2001 – Lil’ Kim Gets Her First Number One Single

“Lady Marmalade” was released on the soundtrack to the Blockbuster film Moulin Rouge, which featured artists like David Bowie, Fatboy Slim and Beck, as well as performances from the film’s stars Nicole Kidman and Ewan McGregor.

2002 – Lil’ Kim Wins A Grammy

When Lil’ Kim was working at Bloomingdales as a teenager, she probably never thought that she’d one day become a Grammy award-winning artist. In 2002, Kim proved that childhood dreams do come true.

2002 – Lil’ Kim Wins A Grammy

The sexy rapper hit the 2002 Grammy’s red carpet decked out in an amazing red leather jacket, boots and blinged out pants. She completed the look with a Coco Chanel-emblemized helmet (though we’re pretty sure she didn’t ride there on a motorcycle). Later in the night, Kim won a Grammy for Best Pop Collaboration with Vocals alongside Christina Aguilera, Pink and Mya for “Lady Marmalade.”

2003 – New Record

Three years after “The Notorious K.I.M.”, Kim released her third studio album, entitled “La Bella Mafia”. The album opened again to positive reviews and sold over 160,000 copies in its first week. She also began collaborating with some of the “new kids on the block” such as 50 Cent and Kanye West.

2003 – New Record

A new record coincided with a new style for Kim. Though she’s always been the daring and unique type, Kim’s style and looks were changing considerably by this time. She was going for much brighter colors and opting for a much softer, natural hair and makeup style, as this picture shows.

2003 – Magic Stick

Lil Kim’s 2003 album La Bella Mafia was a huge hit, but it was also a groundbreaking release that marked a changing music industry. The single “Magic Stick,” which featured the popular rapper 50 Cent, was unusual in the sense that it had no physical release. The single had no music video and was only available via download – something that’s increasingly more common in 2017, but was practically unheard of in 2003.

2003 – Magic Stick

Despite having no physical release or video, “Magic Stick” debuted at number 75 and peaked at number two on the Billboard Hot 100. It also received massive airplay and peaked at number one on the airplay chart, spending a total of 24 weeks in the Hot 100.

2003 – Toxic Relationship

Around this time Lil’ Kim entered into a toxic relationship with Damon Hardy. It was short lived, and Kim was the victim of domestic abuse at this time as well. A year later during an interview, she detailed how she had suffered black eyes and broken bones as a result of the abuse.

2003 – Toxic Relationship

She also had to have several nose jobs to fix the damage from being punched in the face. This explains why her nose looks different in this picture. She still looks naturally beautiful, as always, though her nose has changed noticeably in shape and size, and it really changes her appearance.

2005 – Lil’ Kim Convicted For Perjury

Things took an unfortunate turn for Lil’ Kim in 2005, though she was set to debut a brand new album. The star was sentenced to a year and a day in prison by Judge Gerard Lynch at Manhattan’s U.S. District Court. She was also fined $50,000 and had to go through three years of probation after her sentencing.

2005 – Lil’ Kim Convicted For Perjury

Kim was facing up to 20 years in prison after she was convicted of lying to a federal grand jury to protect friends involved in a shootout outside of a radio station. The rapper honorably admitted to her wrongdoings, which resulted in a lenient sentencing, and said, “This is the toughest thing I’ve ever been through.”

2005 – The Naked Truth

2005 was a big year for Lil’ Kim who released her fourth studio album and last album with Atlantic Records, The Naked Truth. The album was released the first day of Kim’s sentencing, where she spent nearly a year in jail. Despite Kim’s incarceration, the album was considered groundbreaking and remains the only album by a female rapper that’s rated five mics by The Source.

2005 – The Naked Truth

Only one of the singles from The Naked Truth charted on the Billboard Hot 100. “Lighters Up,” which was released on September 13, 2005, peaked at number 31, but “Whoa,” the second single, only charted in the U.K. Though just one of the singles charted in America, The Naked Truth debuted at number six on the Billboard 200 and sold 119,000 copies in its first week.

2005 – Changing Looks

By the mid-00s it was becoming clear that Lil’ Kim had gotten cosmetic work of some kind done. She still looks good here, don’t get us wrong. But, she looks noticeably different to how she did just a few years back. Her image, style, and appearance have been altered quite a bit.

2005 – Changing Looks

She looks very pretty and elegant here, and it’s a big departure from her in-your-face MTV outfits of yesteryear. Perhaps this is her reinvention as a more mature and professional artist? Whatever the reasons, we certainly think Kim still looks radiant, in fact, she kind of resembles Janet Jackson here.

2005 – MTV VMA Awards

Do you remember Kim’s MTV VMA outfit from 2000?! Well, this is a million miles away from that. Even in front of the cameras, it seems that our favorite female rapper is keen to tone down her loud style and adopt a classier and more elegant fashion sense.

2005 – MTV VMA Awards

Here she looks like she could be a Hollywood superstar, dressed in a beautiful dress, and with flawless hair and makeup. This is the Lil’ Kim we think looks the most comfortable; she’s found her identity, and she looks fantastic. You can see in the background how much the photographers are lapping it up as well.

2012 – Lil’ Kim Returns With Return of the Queen Tour

Lil’ Kim announced her return to the music scene with 2012’s The Return of the Queen Tour. It was the artist’s first tour since 2010 and was wildly successful. The tour had 22 shows around North America and grossed $6 million.

2012 – Lil’ Kim Returns With Return of the Queen Tour

In the Spring of 2012, Lil’ Kim announced the first 11 dates of her tour, with extra dates added the following month. She featured a number of notable opening acts including Eve, Kelly Rowland, Lil’ Mama, Da Brat and City high. She also paid tribute to The Notorious B.I.G. by performing the song “One More Chance” during her set in Milwaukee.

2012 – In Concert

Well, as you can see, the more demure and reserved Kim didn’t last too long. Here is a picture of her in concert just a few years ago. She looks even more like Janet Jackson here and also has elements of Madonna and Lady Gaga. That’s a loud and shiny outfit, harking back to the Kim of old.

2012 – In Concert

Her facial appearance has also changed a lot, but she’s still recognizable as being herself. The big, styled, blonde hair is back, and this almost gives her the look of being a different person. She was finally in the throes of recording music for her long awaited new record around this time too.

2013 – Lil’ Kim Finally Heals From Biggie’s Death

The loss of Biggie Smalls was a really tough pill to swallow for Lil’ Kim. It’s no secret that it took her many years to recover, but over a decade later, she admitted she was finally doing well.

2013 – Lil’ Kim Finally Heals From Biggie’s Death

In an interview with RapFix Live, Queen B was asked how it was dealing with the loss of her partner in crime. She said, “That’s a very tough question because it took me so long — super long to deal with the loss of a person who was such a huge impact in my life.” She continued, “I’m just now getting over that fact, and it’s how many years later?”

2013 – Lil’ Kim Reclaims March 9th

When Biggie was tragically murdered on March 9, 1997, Lil’ Kim vowed to never celebrate that day. She spent her career dodging events and declining offers to appear anywhere in order to mourn the loss of her dearly departed partner in crime.

Lil' Kim.jpg

In 2013, Lil’ Kim finally, finally decided to reclaim that terrible day as one of celebration when she appeared at club Glazz in Queens, New York. “That’s my first event ever on March 9 because I used to get offered events a lot and I said ‘no,’ ” she said. “I never celebrate that day. It’s so funny because I can always feel when that day is approaching. I get so depressed. I get so sad. It happens before March, in February. I can feel it coming and I used to all say ‘no.’

2013 – MTV Awards

Ummm, what? Okay, well we knew Kim’s face and style were changing over the years, but it’s always felt like a gradual thing. This, however, is a huge departure from the norm. This is a photo from the MTV Video Music Awards in Brooklyn in 2013, and we’re sure you’ll agree that Kim looks… well, not like Kim.

2013 – MTV Awards

We don’t really get what’s going on here, but Kim looks almost unrecognizable from the woman we know. She has clearly had quite a bit or work done to her face, and it might be in danger of getting out of hand. Her nose, eye and face shapes seem to have been entirely altered.

2016 – A Different Woman

Looking at this picture you would not even think we were talking about the same person. The Lil’ Kim in this picture has much lighter skin and more pointed features than in recent years. It also looks like she may have had filler in her cheeks as well.

2016 – A Different Woman

This snap shows her on the red carpet at the prestigious Angel Brinks Fashion 5 Year Anniversary Celebration. She has always been known for being eccentric and flamboyant, not the sort of woman you would forget in a hurry! But we feel her look here is taking that to a whole new level!

2017 – Black Widow

Though Lil’ Kim hasn’t released a full length record since The Naked Truth, she has released a number of mixtapes and stayed active (though relatively quiet) within the music scene. Recently, Lil’ Kim announced via her Instagram account that she’s planning to release a brand new full length album called Black Widow. This will be her first full length album in 12 years.

2017 – Black Widow

Black Widow will feature a myriad of awesome collaborations with major female rap stars. Missy Elliot and Iggy Azalea are already listed as collaborators alongside Puff Daddy and Dej Loaf. As of now, the album is set to have eight songs. Kim will release this with Atlantic Records and her label International Rock Star Records.

2018 – The Black Widow Tour

Lil’ Kim has been quiet in the music scene since 2012, though she remains a very notable figure; however, the artist is planning a major, major comeback. Lil’ Kim has already planned a headline tour for 2018 (we know, it’s so far in advance but the Queen does what the Queen wants).

2018 – The Black Widow Tour

The Black Widow Tour will be Lil’ Kim’s first tour since 2012 and will mark her return to music. The tour will support her brand new album Black Widow which is expected to drop in February of 2017. While we’re not sure who will open the tour, we do know that Iggy Azalea, Dej Loaf, Puff Daddy and Missy Elliot are likely choices considering they contributed to her album.