15 Most Disappointing Legacies In Rap and Their NBA Counterparts, Ranked

Who failed most to live up to their potential?
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In A Bronx Tale, Sonny famously tells Calogero that “the saddest thing in life is wasted talent.” Bobby DeNiro’s wisdom echoes a theme basketball fans are far too familiar with: unfulfilled potential.

The annals of NBA history are peppered with superstars who never fulfilled their promise. Some are struck down by the basketball gods and suffer career-altering injuries; others fail to reach their potential for reasons we’ll never understand. Nevertheless, these players are remembered equally as much as those who did live up to the hype, for in the game of basketball, like in the game of life, we spend excessive time asking "What if?"

This concept can be extended to the rap game. Since hip-hop’s humble beginnings, far too many rappers have retired with disappointing legacies. Rap’s What Could Have Been Club is made up of victims of either tragedy or the hype machine—which swallows up potentially great rappers and spits out cautionary tales.

Since basketball players and rappers are viewed through this same lens, it’s time to rank the 15 members of Hip-Hop’s Unfulfilled Potential Club and their NBA counterparts. Who failed most to live up to their potential?

15. Juelz Santana is Shawn Kemp

Santana’s Ceiling: Top-five MC of his era; Top-40 MC ever
Kemp’s Ceiling: Top-10 PF ever; Top-40 NBA player ever

The best sidekicks in NBA history, just like the legendary Robins in the rap game, are the select few who’ve excelled in the second-banana role largely because they know their place and have no intention of wrecking the pecking order. In basketball, it’s players like Scottie Pippen, young Kobe Bryant, old Kareem Abdul-Jabbar, and old Dwyane Wade; in hip-hop, its hype men like Memphis Bleek, Lil’ Cease, Proof, and Flavor Flav.

Another branch of the sidekick tree, though, is comprised of guys who-while recognized as the junior to their respective alpha-dog-might’ve actually been the Batman in the relationship. Enter Shawn Kemp and Juelz Santana.

Reign Man was the No. 2 to Gary Payton’s No. 1, despite the fact that he was, perhaps, the best player on a Seattle team that averaged 58 wins over a five-year stretch from 1993 to 1997. During Seattle’s 1996 run to the NBA Finals, a nine-game stretch (Games 5–7 of West Finals, through Game 6 of the NBA Finals) saw Kemp average 25 PPG, 12 RPG, and 3 BPG. Most impressive, against the 72-win Bulls, he was arguably the best player (MJ included) in the series. For whatever reason, though, the 26-year-old Kemp hit a wall after being traded to Cleveland before the 1997-98 season. If he continued to amass All-NBA nods, he would’ve retired as one of the ten greatest power forwards ever.

Vice President of the Diplomats, Juelz Santana was overshadowed by Dipset leader Cam’ron. When the pair appeared alongside one another on many of the group’s hits, though, Santana’s performance suggests otherwise. A teenager at the time, Juelz showcased his superstar potential on Cam’ron’s “Oh Boy” and “Hey Ma,” before arguing his case as the alpha-dog of Dipset on their compilation LP Diplomatic Immunity. As a result, Santana was tapped as the future of hip-hop’s ruling class during the lead-up to his debut album. But by his 25th birthday, his solo career had sputtered on the back of two so-so full-length offerings, 2003’s From Me to U and 2005’s What the Games Been Missing.

14. Kurupt is Rasheed Wallace

Kurupt’s Ceiling: Top-five MC of his era; Top-20 MC ever
Wallace’s Ceiling: Top-10 PF ever; Top-50 NBA player ever

Rasheed Wallace could’ve been the best power forward of all-time; instead, he’s remembered as the captain of the NBA’s Headcase team, not to mention the prevailing face of laziness and wasted potential. At 6’11, with a 7’4 wingspan, Sheed could dominate on both ends of the floor: he was strong enough to battle the best low-post scorers and long enough to protect the rim. On offense, he possessed an impeccable low-post game, capable of stretching the floor with his three-point range.

This ability to heat up behind the arc-at a time when power forwards were supposed to play with their back to the basket-helped Sheed redefine and revolutionize the position. Unfortunately, his knack for earning technicals and laziness prevented him from going down as one of the best ever.

Like Sheed, Kurupt was a once-in-a-generation talent who should’ve been remembered as one of the best of his generation. He became a West Coast legend in the battle scene and a lyrical assassin who’s recognized as one of the greatest freestylers in hip-hop history. After meeting Snoop Dogg and signing with Death Row, Kurupt submitted a handful of scene-stealing features to Snoop’s Doggystyle, including an iconic verse on “Aint No Fun.” But after teaming up with Daz Dillinger to form The Dogg Pound-and releasing their exceptional debut Dogg Food, in 1995-Kurupt waited four years before trying his hand at a solo career.

In retrospect, he and Sheed just didn’t want it enough. Then again, perhaps they were satisfied knowing they had all the skills to be one of the best; to hell with having to prove it.

13. Cam’ron is Tracy McGrady

Cam’ron’s Ceiling: Best MC of his era; Top-25 MC ever
McGrady’s Ceiling: Top-five SG ever; Top-40 NBA player ever

For a five-year window from 2001 to 2005, young basketball fans believed that T-Mac would be remembered as the Michael Jordan of his generation. During a period that saw Shaq and Duncan jostle for the best-player-alive title, Iverson and KG capture one-off MVPs, and Kobe become the most-popular young NBA star, it was T-Mac who-having already cemented his status as the league’s best scorer-had the most potential; the question wasn’t if he would snatch the throne, but when.

By his 28th birthday, T-Mac, a 2017 Naismith Memorial Basketball Hall of Fame inductee, had already submitted a resume worthy of being mentioned among the 75 greatest players ever: two-time NBA scoring champion, seven-time All-Star, two-time All-NBA first team, three-time second team, and two-time third team. Just entering his prime, the possibility of McGrady retiring as one of the 30 best players in NBA history seemed inevitable; the basketball gods, though, had other plans.

Following the 2007–08 season, 28-year-old McGrady underwent shoulder and knee surgeries; from then on, he was never the same. The speed at which he went from superstar to bench player to out of the league is unprecedented: In 2008, he earned his eighth straight All-NBA nod; by 2010, he was playing 35 games a year and averaging 8.2 PPG, 3.1 RPG, and 3.2 APG; come 2012, he was out of the league at the age of 32.

Cam’ron, like T-Mac, is not one of the first guys mentioned when discussing hip-hop’s Unfulfilled Potential Club, largely because at his peak he was as big as any rapper on the planet. In 2002, he hit his stride at the perfect time: the throne was up for grabs, with JAY-Z set to retire, Nas past his prime, Eminem and DMX two years removed from their respective apexes, and 50 Cent a year or so out from grabbing the Best Rapper Alive title.

From 2002 to 2004, Cam’ron was—aside from Fiddy— the most popular MC in the game. He was coming off back-to-back platinum albums (2002’s Come Home With Me and 2004’s Purple Haze) and had pioneered Dipset movement, with Juelz Santana and Jim Jones becoming stars in their own right. Only 28 years old, Cam was set to own the 2000s in the same way that JAY-Z owned the second half of the ‘90s. Cam, though, failed to capitalize on his hype. Just two years later, 2006’s Killa Season flopped, and he promptly disappeared for a long hiatus; Killa Cam, only 30, was washed.

12. Fabolous is Chris Webber

Fabolous’ Ceiling: Top-five MC of his era; Top-25 MC ever
Webber’s Ceiling: Best PF ever; Top-20 NBA player ever

Compared to the greatest players of his era, Webber doesn’t have a crowning achievement. Duncan, Kobe, and Shaq have multiple MVPs and titles; KG and Dirk followed up MVPs by winning a ring while still in their primes; Iverson has the 2001 MVP season and Finals run; Nash has back-to-back MVPs; Kidd was the league’s best point guard for five-straight years; Pierce has the 2008 title run; Allen had titles with the Celtics and Heat; T-Mac won back-to-back scoring titles; Carter has his iconic 2000 Slam Dunk Contest performance.

Webber’s greatest accomplishment? Sacramento’s Game 7 loss in the 2002 Western Finals. Of course, we forget that over a five-year stretch (2000–04), Webber was one of the 10 best players in the league; and, from 2001 to 2003, a top-five guy. He was the first true point forward; someone capable of controlling the offense from the post and perimeter, he was explosive, had a great jumper, and could run the break.

Still, Webber should’ve been better; a skillset like his guaranteed multiple MVPs, an annual slot on the All-NBA first-team, and at least one championship. For whatever reason, though, he never had it—particularly, the killer-instinct needed to be transcendent. As such, we’ll remember him for what he was: a very, very, very, very, very good player who wasn’t quite great.

Fabolous is familiar with the fine line between being good and great. He exploded into the mainstream in the early-’00s-during New York hip-hop’s third golden age-arriving on the heels of JAY-Z and DMX, alongside fellow up-and-coming MCs Ja Rule and Cam’ron. From the jump, Fabolous had the highest ceiling of the three: he was more charismatic than Ja Rule, and more lyrical than Cam; more than anything, though, he sounded, looked, and carried himself like a guy who’d one day hold the Best Rapper Alive title.

A Brooklyn native himself, Fab was next in line to grab the torch that was passed down from Brooklyn MCs Big Daddy Kane, Biggie, and JAY-Z. Hip-hop fans will never understand what prevented Fabolous from reaching his ceiling. While he does have a history of commercial success on par with many of the city's biggest stars, his lack of a bona fide classic LP or timeless, deep album cuts makes one thing certain: Fab, like C-Webb, is very, very, very, very good but not quite great.

11. Nicki Minaj is Dwight Howard

Minaj’s Ceiling: Best MC of her era; Top-20 MC ever
Howard’s Ceiling: Top-five Center ever; Top-25 NBA player ever

Twenty years from now, an entire generation of aspiring basketball players are going to come across Dwight Howard’s accolades and think, “Wow, why didn’t my dad ever tell me about Dwight Howard?” On the surface, his resume is too good to be overlooked: By his 26th birthday, Dwight had made first-team All-NBA five straight years and was the NBA’s Defensive Player of the Year for three years running.

Comparably, here’s how the seven-best centers of all-time fared in both categories by the time they reached 26: Russell (one-time first-team, zero DPOYs), Wilt (three-time first-team, zero DPOYs), Kareem (three-time first-team, zero DPOYs), Shaq (one-time first-team, zero DPOYs), Hakeem (three-time first-team, zero DPOYs), Moses (one-time first-team, zero DPOYs), Ewing (zero, zero).

So, yes, Dwight was on pace to be one of the best centers ever. We spent the first half of the decade bracing for him to transform into early-’00s Shaq, who, like most great big men, took the leap once he reached his late-20s. Instead, Dwight took a step backward. Which is why those of us who remember his career will always feel like he left something on the table. Sure, his resume will suggest otherwise; but if you were there, you know.

Our expectations of Dwight after he dragged the Magic to the ‘09 NBA Finals were similar to that of Nicki Minaj post-”Monster.” After witnessing the rookie rapstress run circles around hip-hop’s GOAT (JAY-Z), the then-Best Rapper Alive (Kanye), and a top-five MC (Rick Ross), with her scene-stealing verse on “Monster,” the ceiling on Nicki’s potential was completely removed. Everything was on the table: Best Female MC Ever….Best Rapper Alive….Top-10 MC Dead or Alive. Nine years later, while she’s remained one of the 10 most popular hip-hop acts of the 2010s, she hasn’t lived up to her early career hype. Even worse, she’s been surpassed by a more successful woman rapper (Cardi B), just like Dwight was usurped by an even better center (Joel Embiid).

10. Big Pun is Larry Johnson

Pun’s Ceiling: Top-five MC of his era; Top-20 MC ever
LJ’s Ceiling: Top-15 PF ever; Top-75 NBA player ever

Back in 1994, Larry Johnson graced the cover of the first ever issue of SLAM. In his third season at the time, LJ was the league’s most promising under-25 talent not named Shaq. At 6’6", 250 pounds, he was built like Zion Williamson, only played like Blake Griffin, equipped with a style built on high-flying dunks and crash-the-boards rebounds.

Johnson followed up winning the NBA’s Rookie of the Year award in ‘92 with a second-team All-NBA nod in ‘93 (averaging 22 PPG and 10 RPG) before his back went out in ‘94. Just like that, LJ’s prime was over before it even began; he was 24 years old.

Just like LJ, Big Pun peaked early, only to be struck down while on the cusp of greatness. After making his commercial debut on fellow Bronx rapper Fat Joe’s second album, 1995’s Jealous One’s Envy, Big Punisher drooped his critically-acclaimed, commercially-successful first album, 1998’s Capital Punishment.

The record not only minted 26-year-old Big Pun a star-he was the first Latino rapper to go platinum, no less-but also cemented his status as one of the best lyrical rappers in the game. Two years later, he died of a heart attack, going down as one of the biggest what-if stories in hip-hop history.

9. Ma$e is Penny Hardaway

Mase's Ceiling: Top-five MC of his era; Top-25 MC ever
Hardaway’s Ceiling: Top-five PG ever; Top-30 NBA player ever

During MJ’s baseball hiatus, while Hakeem cemented his status as alpha-dog of the league, Penny was the odds-on favorite to follow in Jordan’s footsteps and become the face of the NBA. In that same breath, Biggie’s death in ‘97 left the throne up for grabs; and while JAY-Z and Nas battled for the Best Rapper Alive title, fellow New York MC Ma$e was poised to own hip-hop’s post-Biggie era.

Penny and Ma$e asserted their dominance early: 24-year-old Penny, by way of back-to-back first-team All-NBA selections in ‘95 and ‘96; 23-year-old Ma$e with consecutive platinum albums, 1997’s Harlem World and 1999’s Double Up. The star-power of both young superstars extended beyond recording booths and basketball courts, too; Penny and Ma$e were equally great behind the scenes as they were in their respective fields, both equipped with a level of charisma and swagger that their peers couldn’t match.

The only thing they weren’t blessed with, then, was longevity. Penny was dealt a cruel hand by the basketball gods, as his prime was derailed by persistent injuries. Meanwhile, Ma$e decided his fate and retired from the rap game while at the absolute peak of his powers. Both guys should’ve owned the early ‘00s; instead, they’re cemented in the annals of hip-hop and basketball history, their brief apexes froze in time as two of the greatest what-if stories in pop-culture history.

8. Lauryn Hill is Derrick Rose

Hill’s Ceiling: Top-five MC of her era; Top-20 MC ever
Rose’s Ceiling: Top-10 PG ever; Top-50 NBA player ever

At this time next year, when rookie Ja Morant’s highlight reel-dunks force talking heads to wonder, “Who’s the most freakishly athletic point guard ever? Russell Westbrook or Ja Morant?,” I-hopefully like most hoops fans who were old enough to drive circa 2010-will hear this, shake my head in disgust and yell “You forgot about Derrick Rose!” at my television, which is the exact response said talking heads prefer.

All joking aside, D-Rose’s legacy is the most disappointing for Millennial basketball fans. MVP of the league at age 22 (the youngest ever to do so), Rose was the first superstar who threatened LeBron’s reign atop the sport-even before Durant and Curry; years before the arrival of Davis and Giannis. Twelve months after winning the 2010-11 MVP, Rose tore his ACL and was never the same. Which brings us to Lauryn Hill.

Lauryn Hill’s 1998 debut, The Miseducation of Lauryn Hill, is her version of D-Rose’s MVP campaign. Twenty years before Drake arrived on the scene, Hill was the first MC who could sing as well as she could rap; and while her hooks were unprecedented, she spit straight bars. Like Rose, Hill’s peak was brief. But despite leaving the game with an unfulfilled legacy, Hill’s imprint on the genre has yet to fade.

7. Canibus is Derrick Coleman

Canibus’ Ceiling: Top-10 MC of his era; Top-30 MC ever
Coleman’s Ceiling: Best PF ever; Top-20 NBA player ever

As a guest on The Bill Simmons Podcast in 2016, Charles Barkley-one of the three best power forwards of all-time, mind you-said the following about Derrick Coleman: 

“I thank god Derrick Coleman never got it… He’s one of the few guys that made me say, ‘That guy scares me right there.’ If that guy ever got his stuff together, they would’ve had to change the rules. That guy had it all. He could shoot threes. He could post up. He had everything.” If that doesn’t convince you that DC had a skill set other players would die for, Sports Illustrated once wrote, “Coleman could have been the best power forward ever; instead he played just well enough to ensure his next paycheck.”

With a guy like Coleman-whose GOAT potential culminated with one All-Star selection and two third-team All-NBA nods-it’s tempting to blame ourselves for overhyping him; but we’re not at fault. DC had all the talent in the world, only to be prevented from reaching his ceiling merely because of laziness.

Which brings us to Canibus. Granted, Canibus, unlike Coleman, was likely overhyped to begin with, his career proof that he wasn’t ready for the Big Time. And yet, no rapper wasted their moment quite like Canibus.

Arriving on the scene at the height of Diddy’s jiggy movement in the late-’90s, Canibus was hardcore rap’s answer to Bad Boy’s shiny suits and bubble-gum production. If you didn’t believe the hype, you did once he dropped “2nd Round K.O.” After beefing with legend LL Cool J, Canibus submitted one of the best diss songs ever, which in turn minted him a star-in-the-making.

But despite having the natural skills necessary to snatch the throne, Canibus squandered his chance by dropping an absolutely awful debut album. As a result, Canibus—like Coleman—is remembered as one of the most disappointing stars of his generation.

6. Snoop Dogg is Bill Walton

Snoop’s Ceiling: Best MC of his era; Top-10 MC ever
Walton’s Ceiling: Best Center ever; Top-10 NBA player ever

Would you rather have 15 years of Wilt Chamberlain or two transcendent years of Bill Walton? Further, would you rather have 15 years of JAY-Z or two iconic years of Snoop Dogg?

Walton, 25, was named NBA MVP and Finals MVP while leading the Trail Blazers to a championship in 1977, in which he averaged a 19–19–5 with four blocks and slapped up an ungodly 20–23–8 with seven blocks in the deciding game. Then, at the height of his powers—and after leading the defending champion Blazers to a 50-10 start in 1978–Walton’s body broke down. He should have been one of the five-best centers ever; instead, he’s the face of NBA Careers Ruined By Injury.

Now, saying that Snoop Dogg didn’t fulfill his potential may seem misguided; he’s one of the best rappers of all times for chrissakes. But, back in 1994, Snoop’s ceiling was limitless. He’s already bodied the best rap album of all-time, The Chronic, (as a guest star, no less), before dropping the biggest debut album in music history with ‘93’s Doggystyle. So, at the time, Snoop was thought to be the God MC, second to Rakim, if that. Over the last 20 years, though, he’s submitted a so-so career for his standards. As such, like the Big Read Head, Snoop has left hip-hop heads with a salty taste in our mouths: yes, he’s one of the greatest; but he could have been much more.

5. A$AP Rocky is Grant Hill

Rocky’s Ceiling: Best MC of his era; Top-25 MC ever
Hill’s Ceiling: Top-five SF ever; Top-20 NBA player ever

Before the Michael Jordan comparisons became ubiquitous, burdening a collection of up-and-coming talents during the late-’90s and early-’00s, Grant Hill was the original heir apparent to His Airness. Arriving at the league in the fall of ‘94, Hill was nothing short of a gift from the basketball gods, a young star who could fill the void left by Jordan and, simultaneously, improve the league’s then-shattered image.

He had the complete basketball package, highlighted by a once-in-a-generation skill-set: otherworldly speed and athleticism; an ability to handle the ball and cover the length of the floor like a point guard; explosiveness around the rim. Even more, he possessed a Jordan-esque image that instantly made him a fan favorite: Like MJ, Hill was good-looking, charismatic, and articulate, while on the floor carried himself like an assassin.

After the first six seasons of his career, before his ankle injury, Hill had a total of 9,393 points, 3,417 rebounds, and 2,720 assists. Oscar Robertson, Larry Bird, and LeBron James are the only three players in league history to eclipse these numbers after their first six seasons.

Granted, A$AP Rocky doesn’t have a legitimate excuse for failing to live up to his potential. But Rocky, like Hill, was the full package: while Drake was the sensitive rapper and Kendrick tapped into the lyrical niche, Rocky touched both sides and operated as the medium. If anything, he was poised to be the JAY-Z of his era: a rapper with commercial potential and technical sensibilities.

Unfortunately for hip-hop heads, Rocky decided to step away at his peak. Since his breakthrough mixtape in 2011, he’s released two albums; in that same span, Drake has dropped five full-length LPs, Kendrick four, and J. Cole four. He could’ve been the Jigga of his generation. Instead, A$AP is more comparable to Kanye: a rapper who latched onto his next hobby (Fashion) en route to forgetting his true potential.

4. Lupe Fiasco is Vince Carter

Lupe’s Ceiling: Top-five MC of his era; Top-20 MC ever
Carter’s Ceiling: Top-five SG ever; Top-25 NBA player ever

Vinsanity never believed in his potential; there’s no other way to explain his legacy. Sure, he’s submitted a 20-year career, is one of the 75 best players in NBA history, and arguably the best dunker the sport has ever seen. But he had the talent to be much, much more. Of all the guys heralded as the “next MJ,” Vince Carter was the only guy whose peers saw his ceiling at limitless; if only he cared. If you insert Michael Jordan’s brain into Vince’s skull, you have the best player of all-time. Sadly, he never came close.

Like Vince, Lupe Fiasco simply didn’t want to be great. After exploding on the scene with a career-making feature on Kanye’s “Touch The Sky,” Lupe minted himself a star with his debut in 2006, Food & Liquor. From then on, he was praised as a lyrical assassin, one sent from the rap gods to save hip-hop from the ringtone era of Mims, Rich Boy, and Hurricane Chris. Except, Lupe never wanted it; having a platform through which he could voice his political messages was enough. It’s just that: we’ll always wonder how big he could’ve been had he leaned more toward commercial fame rather than an underground following.

3. The D.O.C is David Thompson

D.O.C’s Ceiling: Best MC of his era; Top-15 MC ever
Thompson’s Ceiling: Best SG ever; Top-10 NBA player ever

Before Michael Jordan and Magic Johnson and Julius Erving, there was David Thompson. And before Snoop Dogg, Ice Cube, and DJ Quik there was The D.O.C. Both pioneers blazed the path that their more iconic peers would follow: Thompson, the high-flying dunk artist who paved the way for Dr. J and MJ, and The D.O.C., an initial muse for Dr. Dre who established the blueprint for Ice Cube and Snoop Dogg.

In the ‘70s, Thompson was God. Listed at six-foot-four, Thompson was closer to six foot two and looks noticeably shorter than his contemporaries on tape. No matter. Thompson would dunk on your head or block your shot in the blink of an eye. But, in the end, he was undone by nose candy, peaking by 24 and washed by 28.

The D.O.C suffered a similar cruel fate. His 1989 solo album No One Can Do It Better came on the heels of NWA’s breakout, and it became a classic, going platinum and earning shout-outs from JAY-Z, among many others. But only three months after its release D.O.C crashed his car while driving home intoxicated from a video shoot. When the arriving paramedics tried to insert a breathing tube, he fought them, which caused his larynx to be scarred. In a flash, his melodic, sing-song flow and famous verbal dexterity were gone. Even more, the forefather of Dr. Dre’s G-Funk was delivered a death blow.

2. Jay Electronica is Greg Oden

Jay’s Ceiling: Top-five MC of his era; Top-25 MC ever
Oden’s Ceiling: Top-10 Center ever; Top-40 NBA player ever

The worst cases of unfulfilled potential leave us wondering whether they were undone by hype, or if the hype wasn’t real to begin with. Greg Oden and Jay Electronica serve as cautionary tales; considered potential all-timers, both guys disappeared before we ever had a chance of finding out the ceiling on their greatness.

A true basketball prodigy, Oden entered college ball heralded as the best big man prospect since Shaq, possessing a skill set that had NBA scouts calling him the second coming of Bill Russell. He dominated as a freshman at Ohio State, posting per 40 minute averages of 21 points, 13 rebounds, and 4.5 blocks per game; then displayed Ewing-like potential as a rebounder and shot-blocker while dominating Joakim Noah and Al Horford in the ‘07 NCAA Championship Game with 25 points, 12 boards, and 4 blocks.

But a few months after Portland selected him first overall in the 2007 NBA Draft, Oden had surgery on his right knee, forcing him to miss his entire rookie season. He’d return and suit up for 61 games in the 2008-09 season, but the damage was done; Oden, looking like a shell of himself, was already labeled a bust. Basketball fans never got the chance to see his potential, just as hip-hop heads were left wondering about the potential of Jay Electronica.

From the jump, Jay Electronica seemed more like a myth or urban legend than an actual rapper. The buzz surrounding Jay began following the release of the 15-minute, spoken word mixtape Act I: Eternal Sunshine (The Pledge), which was posted on his MySpace in 2007. Two years later, “Exhibit C” hit hip-hop like a meteor. Ten years on, the Just Blaze-produced single remains Jay Electronica’s ‘07 NCAA Championship Game moment, transforming him from an underground enigma to the hottest rookie in the game. It’s impossible to overstate the excitement in the aftermath of “Exhibit C;” Jay’s performance had everyone convinced that the Messiah had arrived to usher in a new hip-hop era. And then poof, he was gone; like Oden, we’ll never know how great Jay Electronica could have been.

1. Big L is Len Bias

Big L’s Ceiling: Best MC of his era; Top-10 MC ever
Bias’ Ceiling: Best SF ever; Top-10 NBA player ever

Regarding Big L’s legacy, Nas said on MTV: "He scared me to death. When I heard that on tape, I was scared to death. I said, 'Yo, it's no way I can compete if this is what I gotta compete with.'" 

When the man considered to be the greatest lyricist of his era, if not the best ever, says that about you, it’s safe to say you have what it takes to be the best ever.

Tragically, Big L never got the chance to fulfill his limitless potential. He died at 24 years old, gunned down outside of his apartment in Harlem on February 15, 1999. At the time, he was poised to snatch the King of NY throne in the post-Biggie era; five years and one year younger than JAY-Z and Nas, respectively, Big L had next.

Even with a small body of work- just one album, a handful of singles and freestyles- the Harlem prodigy proved he had the talent to be the most respected MC of his era- the true embodiment of the old adage, your favorite rapper’s favorite rapper. The saddest thing, then, is that we’ll never know what he was capable of; unlike fallen heroes like ‘Pac and Big, Big L was taken from us when he was on the cusp of superstardom.

The same goes for Len Bias. Drafted by the defending champion Boston Celtics No. 2 overall in the 1986 NBA Draft, Bias was heralded as the answer to Michael Jordan- an explosive, shit-talking playmaker who was poised to go toe-to-toe with MJ during the ‘90s, just as Magic and Bird battled in the ‘80s. Unfortunately, on the night he was drafted, the 22-year-old soon-to-be-superstar-rookie died of a cocaine overdose. And just like that, the rival MJ always needed, not to mention a natural talent who could’ve gone down as one of the ten greatest players in the history of the sport, was gone.

Oh, what could have been…

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