When it comes to rappers, some names have certainly stood the test of time. Indeed, artists such as Jay-Z, Eminem and Dr. Dre have maintained healthy careers long after making their debuts. However, for every hip hop success story, there is an artist who failed to stay in the spotlight. From lost potential to scandalous falls from grace, these stars of yesteryear are no longer the big deal they once were. It’s just a pity that no one’s told them that yet.
Despite rapping for the past ten years, Tyga is perhaps best known for his relationship with Kylie Jenner. Even the “Rack City” star – who broke up with the Kardashian clan member in 2017 – believes this to be the case. “It overshadowed a lot of my talents and a lot of things I worked hard for,” he told Big Boy TV in 2017. Even a 2016 signing by almost-brother-in-law Kanye West couldn’t resuscitate this player’s career.
19. Iggy Azalea
She was so “Fancy” when she hit the scene in 2011, but time has not been kind to Iggy Azalea. Due in part to a change in management, Azalea has seemingly lost the respect of those in the hip hop community. And her new material has failed to enthrall fans like her previous work. For example, the star’s recent “Mo Bounce” was named one of the worst singles of 2017 by YouTube critic Anthony Fantano.
18. Soulja Boy
Back in the early days of social media, artists such as Soulja Boy pioneered the use of sites like YouTube and MySpace to get their music heard. As a result, his 2007 single “Crank That” topped the Billboard Hot 100 for seven weeks. But the rapper – a.k.a. DeAndre Cortez Way – couldn’t replicate this success and his album The DeAndre Way sold an abysmal 56,000 copies upon its 2010 release. Still, that hasn’t stopped him releasing music well into the present day.
17. Azealia Banks
We all expect rappers to engage in occasional feuds, but Azealia Banks proved too toxic even for hip hop fans. Following the runaway success of her 2011 single “212,” the rapper derailed her career with a series of outbursts that definitely crossed the line. Besides calling out treasured acts like Beyoncé, Banks has received accusations of racism and homophobia through her barbs. She was even suspending from Twitter in 2016 for a racist social media attack on Zayn Malik.
In 2005, Houston-based rapper Chamillionaire climbed to the top of the charts with his single “Ridin’.” As a sign of its fame, the single – which stayed at the top spot for two weeks – even inspired a parody by “Weird Al” Yankovich. That being said, the hip hop star’s follow-up L.P. Ultimate Victory didn’t receive such crossover success. Some publications – such as Hip Hop Vibe – pointed to the album’s toned-down lyrics as the reason for its failure.
Thanks to the tutelage of fellow artist Ludacris, Chingy quickly became a star in the early noughties. Nevertheless, success soon went to the young “Right Thurr” rapper’s head. And – after slamming Ludacris’ label Disturbing Tha Peace in the press – Chingy failed to break the charts with 2007’s Hate It Or Love It. To this day, he still blames his former label for the L.P.’s misfortunes, “They didn’t push it. They didn’t promote it,” he told Buzzfeed in 2014.
There aren’t many rappers who can claim to have set records, but Twista – a.k.a. Carl Mitchell – is one of them. In 1992, the “Slow Jamz” star was named World’s Fastest Rapper by the Guinness Book of World Records after spitting an incredible 598 syllables in 55 seconds. Though still releasing records, Twista isn’t recognizable to modern hip hop fans. In fact, contestants on To Tell the Truth failed to recognize him when he appeared on the game show in 2017.
13. Paul Wall
Like fellow Houston rapper Chamillionaire, Paul Wall has had a less than stellar career in recent times. After success as an independent artist, the star managed to break into the mainstream with 2005’s The Peoples Champ. However, Wall couldn’t live up to the hype and he was dropped from label Atlantic after follow-up LP Get Money, Stay True’s commercial failure. Recently, he was charged and acquitted of manufacturing drugs – a fact that hasn’t helped the rapper’s reputation.
During the 1990s, there wasn’t one person who couldn’t recite Coolio’s “Gangsta’s Paradise” word for word. Indeed, the song became 1995’s biggest-selling single in the U.S. and even earned its creator a Grammy. Since then though, Coolio has seemingly struggled to stay in the spotlight going so far as to appear in the U.K. version of Celebrity Big Brother in 2009. He even auctioned off the rights to his biggest hit in 2013 to fund becoming a celebrity chef.
11. Flavor Flav
As hype men go, there are few names as celebrated as Flavor Flav. And – as the second-in-command of pivotal hip hop group Public Enemy – he both popularized the term and became one of ’80s rap’s biggest stars. Nevertheless, Flav – a.k.a. William Jonathan Drayton – was never as skilled on the mic as Public Enemy cohort Chuck D. Subsequently, the star is probably best known to today’s rap fans as the host of reality series Flavor of Love.
By all means, controversy can help a rapper on their way to success. And Khia used this to full advantage with her profane “My Neck, My Back (Lick It),” which gained the Tampa-based star notoriety in 2002. Unfortunately, she never managed to repeat that scurrilous single’s success and she is now mainly remembered as a one-hit wonder. But that hasn’t stopped Khia taking on bigger stars like Beyonce online. “Woooooooo im scared of the Beyhive,” she sarcastically tweeted in 2013.
First generating buzz on the underground circuit, Washington D.C.-based Wale became the envy of indies everywhere when he signed to Interscope for $1.3 million in 2008. However, Wale’s major-label debut wasn’t quite the success his managers had hoped. And not even a guest spot from Lady Gaga could push single “Chillin’” up the charts. These days, the rapper is arguably worse off than before. Recently, his 2017 LP Shine sold just 25,000 units in its first week.
If the name J-Kwon doesn’t ring a bell then that’s probably because the rapper hasn’t had a hit since 2004. Though his single “Tipsy” put the artist – a.k.a. Jerrell C. Jones – on the map, J-Kwon has since been on the down-low. In fact, his label Gracie Entertainment even reported the reclusive rapper missing in 2010. Nevertheless, J-Kwon still has important fans. For instance, Kanye West called “Tipsy” his favorite song during a 2013 interview with The New York Times.
7. Lil’ Kim
After her 1990’s discovery by the Notorious B.I.G., Lil’ Kim paved the way for a future generation of female rappers. But though the provocative star could boast of three platinum albums in her heyday, the artist is now probably best known for her long-running feud with Nicki Minaj. Moreover, issues with the I.R.S. have put the star in financial dire straits, and it was reported in 2016 that Kim’s $3 million New Jersey home was close to foreclosure.
6. Ja Rule
Many hip hop artists try to crossover from music into other business ventures and Ja Rule was no exception. However, the Queens-based artist – best known for hits such as “Always on Time” with Ashanti – probably should have stuck to rapping. To wit, the star’s involvement in the ill-fated Fyre Festival last year – which drew comparisons to a refugee camp by its overcharged patrons – led to legal actions against him. “I truly apologize as this is NOT MY FAULT,” Ja Rule insisted on Twitter.
5. Foxy Brown
Like fellow female MC Lil’ Kim, Foxy Brown paved a path for female rappers in the ’90s. And following her 1996 debut, the star has sold an impressive 13 million albums and received a Grammy nomination for 2001’s Broken Silence. In 2007, Brown formed her own independent label – a venture that has proved less fruitful than she presumably hoped. Since the signing, she has released one mixtape – Brooklyn’s Don Diva – which sold only 25,000 copies.
4. Bow Wow
Within the hip hop community, status is everything. But Bow Wow – a.k.a. Shad Gregory Moss – fell far from grace after fans noticed him exaggerating his lifestyle. In 2017, the rapper – who found fame with 2000’s Beware of Dog – instagrammed a snap of a private jet he was supposedly flying on. Nevertheless, he was caught out after a fellow flyer saw Moss sending sitting across from them on the same commercial flight mere moments after sharing the post. Never lie, kids.
3. MC Hammer
Best known for his hit 1990 single “U Can’t Touch This,” MC Hammer was one of hip hop’s first major stars. And – thanks to his iconic baggie pants and a media empire that included toys, cartoons and Taco Bell commercials – he helped bring the genre into the mainstream. Nevertheless, the extravagant star went bankrupt in 1996 and has since slipped into the music wilderness. But despite his dip in popularity, Hammer is surprisingly still recording and performing to this day.
2. 50 Cent
Unlike many artists on this list, 50 Cent can still command a great deal of respect among the hip hop community. Notably, in 2013 Complex deemed the “In Da Club” star one of the top five rappers of the 2000s. However, Fiddy’s commercial standing has slipped considerably. For example, his last L.P. Animal Ambition sold just 124,000 copies in 2014. Meanwhile, fans unwittingly admitted that the artist was “washed up” during an embarrassing Jimmy Kimmel Live skit in 2017.
1. Vanilla Ice
It’s fair to say that Vanilla Ice – a.k.a. Robert Matthew Van Winkle – is something of an acquired taste. Since the success 1989’s Platinum-selling “Ice Ice Baby,” Ice has been derided by rappers and fans alike. Even Eminem once claimed that the star’s music almost dissuaded the future-superstar from entering the business himself. Today, Van Winkle can be seen on reality TV and nostalgia festivals such as I Love the 90’s. It may not grant much exposure, but a gig’s a gig, right?