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Could've, Would've, Should've: 6 Rappers Who Never Reached the Mountaintop

Hip-hop is a mountain, but the music industry is a revolving door, and half the battle is getting in and managing to stick around.
6 Rappers Who Could’ve, Should’ve, But Never Reached the Mountaintop

Hip-hop is a cultural space many enter with immense talent and giant aspirations. Practitioners see the art form as a mountain to be climbed and conquered; to leave their flag at the top is the quest that most artists set out to accomplish. Over the years, spectators have witnessed and cheered as waves of promising prospects attempted to master the 45-year-old behemoth.

We pick our favorites MCs and foresee their forthcoming reign the same way athletic scouts can see the promise of future draft picks. But just like sports, having all the potential to be great doesn’t guarantee a championship ring or entrance into the hall. In rap, more often than not, great potential falls short of expectations. Hip-hop is a mountain, but the music industry is a revolving door, and half the battle is getting in and managing to stick around.

In a post-LimeWire artistic economy when the act of recording music is available to everyone, more artists than ever before are attempting to "make it." In this massive climate of creators, rappers who showcase tremendous talent but don’t make it to their speculated destination can be broken into three simple categories: Could Have Been a Superstar, Achieved Success but Fell Short of Potential, and It’s (Still) Not Too Late.

There’s no E for effort, no trophy for trying, just the music and the history of what transpired. The mountain stands, the door spins, and the cycle continues.

Could Have Been a Superstar

Jay Electronica

The Mountain Dew commercial made me a believer in Jay Electronica’s star power. Without an album or radio single, he was on national television being endorsed by a large corporation. In the underground community, he was the selected savior of rap lyricism as a mastered artform. In the mainstream, both Diddy and JAY-Z were at war over ushering in the age of Electronica. Look no further than the Just Blaze-produced “Exhibit C” for proof of how one single had the power to throw hip-hop off its axis.

The mystic, New Orleans-born nomad had the eyes of the industry, the ears of the people, and all the poetic power to be an almighty force like hip-hop’s Thanos, but at the peak of his attention, he decided to gracefully merge into the margins.

Hip-hop will wonder well into her old age what turned the savior to silence before the release of his highly anticipated debut.


HBO displayed Saigon’s face before his debut album could grace the racks of Best Buy. Unfortunately, the emerging rap deity guest starring on a show with the popularity of Doug Ellin’s Entourage never translated into a Hollywood ending. To say the Brooklyn-born rapper was a big deal in the early and mid-2000s would undervalue the overzealous excitement that once surrounded him. Hip-hop blogs and an entire underground community of rap enthusiasts saw in his music a lyrical gladiator who rhymed with the spirit of 300 Spartans.

He had no gimmick or jingle; it was grand lyricism and hard-knock storytelling that placed him alongside Just Blaze as his production supplier and Atlantic Records as the ship that would carry him to mainstream glory. Sadly, the ship sunk before leaving the docks. Saigon floated in an ocean of setbacks before releasing his debut album, The Greatest Story Never Told, five years after the height of his buzz.

Saigon could’ve been an all-time great, but instead, he's another tragic case of a major label treating a diamond like a piece of disposable coal.

Honorable mentions: The Cool Kids, Rich Gang

Achieved Success But Fell Short of Potential


2019 will mark the 10-year anniversary of B.o.B.’s “Nothin' On You,” a 3x Platinum single that paired his charismatic style with a melodious hook from young Bruno Mars. It was pop magic. Their ascension to the top of Billboard wasn’t amateur's luck, either. The two cracked the code and appeared confident and comfortable in the realm of budding pop stardom.



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There’s a Gemini duality about B.o.B. that kept him from committing to chart-topping. He clarified the two sides on his 2009 mixtape, B.o.B. vs Bobby Ray. Plenty of rappers have made a gimmick out of an artistic split personality—see also: T.I.—but there was a genuine contrast between B.o.B's harder raps and the soft pop stylings of Bobby Ray. Lacking a true balance, the Atlanta native either kept the streets fed with anthems or pumped out crossover attempts tailored for radio—rarely did the two co-exist simultaneously.

Once Bobby shared his views about Earth and various conspiracy theories, it was game over. Sure, he's still capable of making music that's enjoyable—2017's Ether is solid—but once you take the red pill there’s no returning to the matrix.


Ab-Soul’s 2012 album Control System eloquently displays why the TDE underdog was quietly becoming a lethal secret weapon. Overflowing with pensive writing, introspective exploration, and a William Burroughs-esque interest in self-medicating, the entire experience is a drug-induced trip, with a black, Carson, California-raised, intellectual hippy as its tour guide. His wizardry was peculiar, yet engaging; intricate without becoming a labyrinth; deeply personal and joyfully clever.

Control System showcased the full package of his artistry while drawing in an audience of believers who were faithful to the Ab-Soul school of thought. Problems arose when the school pursued lesson plans that diverged from what made his breakout album compelling. The two albums that followed swallowed listeners in overthought riddles, exhausting lyricism, and colorless journeys to the center of nowhere. 

Ab’s recent performance on Black Panther The Album inclusion “Bloody Waters” displays a return to form—the artist fans hope to hear when they press play—but after years of partial letdowns, it’s hard to become hopeful that his next album will pick up where Control System left off.

Honorable Mentions: Cassidy, SpaceGhostPurrp, Papoose

It's (Still) Not Too Late...


Underneath the spotlight isn’t a natural setting for every artist who steps onstage. Raury didn’t appear alien beneath the blinding glow; the young man has always stood tall despite a series of disheartening career setbacks. Being young in this business comes with growing pains, stumbles, and falls that leave lasting scars instead of temporary scabs.

Since the release of his breakout single, “God’s Whisper,” Raury has experienced the highs of opening for OutKast and being able to play music for Kanye West, but also the lows of separating from his major label and parting ways with the management team that introduced him to the world.

The beauty of starting over, however, is a clean slate. The beauty of independence is creating the rules you play by. Returning to the spotlight as a refined, reinvigorated artist could make the second phase of his career bigger than the first. Raury’s destiny is ultimately in his hands. Plus, he's only 21.

Rich Homie Quan

In 2013, during an interview with MTV, Drake labeled Rich Homie Quan’s “Type of Way” the song of the summer. It’s a flashback to a time when the Atlanta melody machine was reaching a new pinnacle of exposure and embrace from giants in every rap circle.

Quan was hot and only growing hotter; the hits kept coming as he paired with Young Thug as Rich Gang, and after their abrupt breakup, he caused the world to dance with 2014 single, “Flex (Ooh, Ooh, Ooh).” But soon after, the serial hitmaker who promised to never stop going in broke his vow and a series of duds fell flat.

Four years later, after some legal and non-legal mishaps, Rich Homie Quan is finding his footing. Rich as in Spirit, Rich Homie Quan’s debut album on Motown, is a refreshing resurrection of the heartfelt, hustle-driven rapper whose future was bright as his jewelry. There’s fire in his gut, maturity in his reflection, and hope that the mountain can still be conquered. I wouldn’t bet against Rich Homie, baby.

Honorable mentions: Vic Mensa, Father, XV 

By Yoh, aka, Thanyohs aka @Yoh31


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