Life’s Not Fair: Artists Who Should’ve Blown Up, But Didn’t Part 2

- By Bossip Staff Categories: Entertainment, For Discussion, For Your Information


The music industry proves that life’s never fair, to anyone, on the daily. Some artists win (and shouldn’t), while others, like the unlucky artists on Pt. 1 (and now Pt. 2), never do.

Here are ten more artists who should’ve blown up, but never did. Take a look.


Left Eye
Without Left Eye, TLC doesn’t work. Chilli’s perfectly-moist baby hairs and T-Boz’s lawn mowerish vocals could’ve been replaced. Left Eye? Bona fide superstar.


The vice President of music’s one album every decade club (Lauryn, Maxwell, D’Angelo and *3 Stacks) dropped the classic debut “1st Born Second” then frolicked in space for 10 years before releasing his follow-up “Airtight’s Revenge.” Now he’s R&B/Soul’s most known unknown.


Young Dro

No human being sees the world through the same color-splashed lens as Dro—hood famous painter of mental masterpieces. Whirlwind-blue, Sad-blue, IHOP-blue? Dro was on a completely-different level than most rappers.


Brooke Valentine

In another lifetime, the sex-oozing R&B vixen has Ciara’s career. Well, a more relevant, less stressful, Matrix-free version of Ciara’s career.


Black Thought (The Roots)

He’ll always be “that dope rappity-rapper in The Roots crew” trapped in Questlove’s shadow and never the “legendary GOD MC” mentioned in greatest rapper of all-time discussions.

Photo credit: Instagram


Glenn Lewis

The promising R&B crooner dropped a timeless gem “Don’t You Forget It” then fell off Earth forever. R&B tragedy.


Cheri Dennis

She had the look, sound and energy to truly win but was signed to Bad Boy where tragically-unlucky artists go to die.


KeKe Wyatt

More famous for stabbing her ex-husband than her incredible voice, KeKe is a prisoner of her insanity-fueled past.


Yummy Bingham (Tha’ Rayne)

Her voice is pure Heaven with a beautifully-smoky twist featured on classic records like De La Soul’s “Much More.” With her debut album shelved, she’s the dopest R&B artist not named Latoiya Williams to never happen.



The Dungeon Family’s first lady could’ve been the Black Lady Gaga but it just wasn’t meant to be. After years battling label politics (and losing), all we have is “Lick”—her only timeless gem.


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