Just Sayin: 10 BIGGEST Underachievers In Music History

- By Bossip Staff Categories: CELEBRITY, Entertainment, For Discussion


For every mega-successful artist are hundreds who never reach their full potential. Since the beginning of time, hype-fueled artists have flourished while others with actual talent failed to evolve into the music icons (or legends) we imagined they’d be. Cruel reality, but that’s life.

Here are the ten biggest underachievers in music history. Take a look.


Lauryn Hill

One classic solo album. One classic group album. One classic movie (“Sister Act 2”). All released 10+ years ago before the insanity, guitar strumming while barefoot and anti-tax conspiracies. In some minds, she’s “iconic” but, let’s be real, she’s more of a beautiful memory than anything else in 2013.



The legendary underachiever dropped a timeless Hip-Hop classic at 19 (“Illmatic”) and was crowned Rap’s chip-toothed Messiah before evolving into a walking punchline who never quite lived up to his incredible potential.



The soulfully-incredible crooner’s heartstring-plucking falsetto made him a Neo-Soul GOD until label-fueled inner-demons left his life, career and cornrows in shambles. Most tragic fall from grace, maybe ever? Yes.


Andre 3000

3 Stacks is one of the greatest rappers ever, of all-time, yet refuses to release a solo album despite his fans’ most passionate pleas. Now that his mother is gone, we may never get one.

maxwell album cover


Vocally-untouchable yet “missing” for most of his career, it’s surreal that he’s not bigger than he is, musically. Rumored to be fighting his label on coming out (which explains the album delays), he’s one of R&B/Soul’s greatest unsolved mysteries.



12 years and four mostly-wack albums later and we’re still waiting on Jada to flourish. Sadly, nobody cares anymore.



She’s the classiest hoodrat in the game with an amazing voice and terrible luck. Brandy waaaaaay more successful and relevant than Monica in 2013? We doubt anyone saw this coming in ’98.


Jazmine Sullivan

She came, inspired millions of scorned women to stalk and vandalize their ex-boo’s car and fell off Earth. Incredibly-talented as both a singer and songwriter, Jaz could’ve been legendary.


Christina Aguilera

Xtina was blessed with once-in-a-lifetime talent and WASTED IT ALL during her tragic career. GREATEST waste of pure talent in music history? No question.



Pepsi Super Bowl XLVII Halftime Show

Queen Beysus of Negronia is widely-considered the greatest artist of her generation and foolishly compared to Michael Jackson (and even Prince) when she’s clearly not on that level.


Ask yourself these questions: What musical impact has Bey Bey had on her generation’s greatest artists? What trends has she started? Twenty years from now, will you still be playing “Video Phone” or “Countdown?” How can an artist so talented only have ONE classic album and a few timeless records?


Fun Fact: Britney Spears has sold over 100 million albums worldwide as one of the best-selling music artists of all-time. Bey? Slightly less. Same generation. But BEY is the greatest of her era? Hmm…


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