Greatness Hip-Hop MLB NFL Rap

Bo Jackson and Lauryn Hill: Legendary Even Without Longevity

Some people are too talented to be confined to just one lane. 

Vincent Edward “Bo” Jackson was the rare two-sport athlete. He could have been a Hall of Famer in both baseball and football. 

Lauryn Hill was the rare two-discipline musical artist. She could have had the greatest career as both a rapper and a singer.

They also shared several other traits in common: reaching incredible heights; colleagues accusing them of being difficult; focusing on their families; and, above all, not being interested in living up to the outsized expectations created by their early acts of brilliance.

Naturally Gifted & Unique

“A really great talent finds its happiness in execution.”

 — Johann Wolfgang von Goethe

Bo Jackson was arguably the most naturally gifted athlete, with the rare combination of size and speed that made jaws drop with his incredible feats like running a 4.13 40-yard dash and blasting 450-foot home runs. An NFL scout once raved about Jackson: “I have not seen anyone faster, quicker, stronger, or more explosive.”

Lauryn Hill was arguably the most naturally gifted hip-hop artist, with the rare combination of an angelic voice and flawless flow that made jaws drop with her ability to deliver a classic 16-bar verse immediately followed by a timeless chorus. Hill “straddle[d] the line between Motown soul, boom bap, R&B, jazz and rap — defying convention and introducing a new standard for genre-bending rappers.”

They may have also taken that natural ability for granted. 

While Jackson left it all out on the field, he was notorious for his lack of work ethic. He never worked out. He wouldn’t develop his game in the offseason. As Jeff Pearlman writes in his excellent biography of Jackson, The Last Folk Hero, “His work habits stunk. His moderate interest in the playbook was irritating. Nothing was crisp or precise.” As a pro baseball player, he wouldn’t study pitchers and never really mastered the ability to hit anything other than a fastball. As a pro football player, he would not know the plays being called and it was not unusual for him to move in the wrong direction. As early as college, he developed a reputation as a “half-assed practice player.” 

Hill has the ability to create magic in the studio, but she has frequently clashed with groupmates and collaborators and become known more for being hours late to her own concerts with no explanation, as well as soap opera-level drama, rather than her musical output. In the past two-decades, she’s released only a handful of solo tracks (one as part of a legal requirement), a single reunion song with the Fugees, and a few scattered features.

Top of the Mountain

“It’s not the mountain we conquer, but ourselves.” 

— Edmund Hillary

Bo Jackson led off the 1989 MLB All-Star Game with a 448-foot home run. In the fourth inning, he hit an RBI single. In the commercial break between the top and bottom of the fourth, Nike unleashed its “Bo Knows” commercial, a spot that immediately became part of the zeitgeist and was instantly validated when the night ended with Bo raising the MVP trophy. Four years earlier, Jackson had won the Heisman trophy as the top collegiate football player in the nation. In less than a half-decade, he had gone from the best football player in the country to (at least for one night) the best baseball player in the country. 

A decade later, Lauryn Hill won five Grammy Awards in 1999, including Album of the Year — a first for a hip-hop artist — for The Miseducation of Lauryn Hill. They went along with the two she won with the Fugees two years earlier for their diamond-selling masterpiece, The Score. Her smooth but powerful combination of soul, R&B, hip-hop, and even reggae expanded the horizons of what pop music could be. A compelling argument could also be made that she “created Beyoncé, Kendrick Lamar and Cardi B.” Hill was in the conversation as both the best singer and the best rapper.

Shooting Stars

“In your life you will meet shooting stars. You will see them, make your wish and see them disappear.”

― Nahiar Ozar

Bo Jackson became an outsized figure not by breaking records or winning championships, but through singular moments that almost didn’t seem real. In an era before the internet, legends grew through the passing of dubbed VHS copies and stories that began with the phrase, “I heard that that he…” and no one was the subject of those stories more than Bo.

There was the Monday Night Football game against the Seattle Seahawks when he ran over the overhyped, trash-talking Brian Bosworth…

…the time he couldn’t stop in time so he ran horizontally across the outfield wall…

…and the breaking of bats over his knee and, once, even over his head (the bat had been cracked on the pitch, but never let the truth get in the way of the legend).

Then there was Tecmo Bo. 

It’s possible that Jackson is remembered as much for what he did in 8-bits as for anything he did on a football field or baseball diamond. Never again would a video game become so entwined with an actual person that it became part of that person’s biography and lore as much as Bo Jackson and Tecmo Super Bowl. The game’s creators were so enamored with Jackson that playing as him was the “ultimate cheat code.” Its impact — and nostalgia — remains to such a degree that even three decades later it is the topic of both a 2017 Kia commercial and a hilarious bit on Family Guy.

Considered by many to be the greatest athlete of all time — in addition to football and baseball, he was also a decorated track and field competitor — Jackson’s jaw-dropping career ended suddenly, even anticlimactically, in the 1990 AFC Divisional Playoff Game when a seemingly routine tackle led to Jackson departing the game and, it turned out, the sport. 

He developed avascular necrosis of the hip, a dangerous condition in which blood supply is cut off from the damaged bone, thereby risking deformity or amputation. Amazingly, despite doctors advising he may never walk properly again, Jackson eventually returned to baseball, even homering in his first at-bat following hip replacement surgery (add it to the legend), but he was a shell of himself, playing two seasons for the Chicago White Sox in 1991 and 1993 and one more for the California Angels in 1994. 

While Lauryn Hill did not have the same type of mythological moments, her career trajectory was almost the exact inverse of Bo Jackson’s. Her rise seemed just as fast and just as unexpected as his fall.

A year after announcing herself as a future star with her turn in 1993’s Sister Act 2, she and her groupmates released their first album as the Fugees. Upon its release, Blunted on Reality sold twelve copies. Twelve. Even the most optimistic fan could have not predicted what transpired next. Their second album became one of the best-selling albums ever — even briefly becoming the best-selling hip-hop album of all time — with more than 22 million copies sold. 

For almost exactly three years, from the release of The Score on February 13, 1996 to the 41st Grammy Awards on February 24, 1999, the music world fawned over Lauryn Hill, both as a member of the Fugees and as a solo artist. Her ability to deliver both classic rap verses and immaculate hooks, often on the same song (“Ready or Not”; “Vocab”; “Fu-Gee-La”; “Doo Wop (That Thing)”; etc.), made her the ultimate dual threat. Combined with the emotional strength and impact her music provided to legions of fans, she came to represent much more than a musical artist

When Hill returned in 2002, it was with a live album, MTV Unplugged 2.0, which found her not belting out powerful ballads or dropping deep 16s, but instead strumming an acoustic guitar and singing folk songs. At one point, her emotions became so strong that there were tears streaming down her face. During one of the spoken interludes, she says, “Fantasy is what people want but reality is what people need, and I just retired from the fantasy part.” 

It may have been what people needed, but the album is not what they wanted. Critics and fans acted as if they were personally offended by it, particularly the long conversational asides in which Hill addresses the audience. The reviews were scathing — Robert Christgau said it was in the running for the “worst album ever released by an artist of substance,” and the headline of Dan Aquilante’s review was simply, “SHUT UP & SING.” (For what it’s worth, I enjoyed the album. While it was not a proper follow-up to Miseducation and Hill’s voice was certainly hoarse and scratchy, I appreciated it for what is was and even found her raw honesty and emotion refreshing and bold.)

Deemed to be Difficult

“I don’t think most people, perhaps not even some celebrated artists, are aware of the battle it takes to be an artist and remain true to what you really think. I don’t even ‘practice’ small talk, so I’m never confused with someone who can be seduced.”

— Lauryn Hill

Both Jackson and Hill have been variously described as difficult, both publicly and behind the scenes. 

It’s not rare for wildly talented people to be on a different wavelength from everyone else. The reasons for this are many — others can’t see what is clear to them; they feel others are holding them back or preventing their vision from coming true; or they’ve simply always gotten what they’ve wanted because their talent always won out. 

This is not confined to strictly sports and entertainment. There are about 103 million Google search results for dealing with talented but difficult individuals, most of them focused on the workplace. 

Part of Bo Jackson’s job as a professional athlete was to interact with the sports media on a daily basis, but he refused interviews and spoke as little as possible. He was hostile to the same people that were chronicling his Paul Bunyan-like feats. Worse, he was prickly with his peers — aloof or even outright mean to teammates and dismissive or rude to players from other teams. When opposing players asked Jackson to trade jerseys or autographs, a regular custom in American pro sports, he would often berate and scream at them. 

Lauryn Hill had already become disillusioned with both the music industry and the media by 2002, so when her second solo album landed with a thud, she retreated into private life. Yet it wasn’t just the suits and the critics with whom she bristled. Hill has been criticized as difficult to work with, with various collaborators and backup band members claiming she often acts erratically, constantly changing her mind, criticizing them, firing bands on a whim, and other diva behavior. That’s not to mention the claim that lying about her child’s paternity is the reason the Fugees disbanded. It’s not only behind the scenes. Her constant tardiness to live shows turned off many fans, but she was rarely apologetic, blaming others, citing the need to “align her energies,” or any other number of reasons as why it was acceptable for her to show up two hours late and only perform for forty minutes. She ultimately addressed all this in a line on “Nobody” from Nas’s King’s Disese II: “I’m savin’ souls and y’all complainin’ ‘bout my lateness.” 

Prioritizing Family Life

“I would say my greatest achievement in life right now — my greatest achievement period is — and I’m still trying to achieve it — is to be a wonderful father to my kids.” 

 — Bo Jackson

Bo Jackson was not Kobe Bryant. He was not psychotic about the game and singularly focused on only becoming the best ever. He treated the sport he played — both of them — more like a job than an obsession. Pearlman writes, “He didn’t live and die with the games he played. He didn’t take stuff home and dwell on it. Why? Family.” Later, he quotes Jackson directly, in response to being asked why he did not stay late after a game: “Listen, my wife is out there waiting on me, and I’m always going to be the first one off that fucking field and the first one undressed and in the shower and dressed and out of here…I’m a team player out on that field. But once we leave that field, fuck everybody I work with, because I am not going to take that shit home with me.”

Similarly, Lauryn Hill was not Jay-Z. She did not have ambitions to conquer the music world — and beyond. Her triumph at the Grammys led to incredible pressure to repeat or even exceed Miseducation, as she became much more than simply an artist: “Her music became religious to some, and that creeped her out. It inspired her to disappear and avoid the expectations of popular media to keep her individuality intact.” Following the tepid and even angry response to MTV Unplugged 2.0, she made “the decision to pull away from the rigors of fame to focus on raising her six children.” She could have attempted to make another classic to secure her legacy and be (even more) lauded by fans and critics, but she chose her family instead. 

Legend Over Longevity

“It’s better to burn out than fade away.” 

 — Jeff Blackburn

Bo Jackson was the only pro athlete in history to be an All-Star in both baseball and football. 

Perhaps it’s counterintuitive, but Jackson’s immediate disappearance (aside from a they-said-it-was-impossible short baseball comeback) cemented his mythical status. We didn’t see him grow old and steadily decline — he was superhuman and then he was broken. There was no in between. It was like when Superman was killed.

Hannah Giorgis, writing in The Atlantic, makes a similar point about Lauryn Hill: “Hill’s legacy lives in the gap between what she has given and what she has kept hidden away. The mystery is itself a kind of genius.” Without proof to the contrary, we can imagine anything — everything! —could have been possible if she hadn not stepped away.

Had Bo Jackson stayed healthy, he could have been one of the all-time great baseball and/or football players.

Had Lauryn Hill kept recording, she would have inarguably been one of the all-time great rappers and/or singers.

But perhaps they were never meant to have the long, stable career. Maybe they were always meant to represent a short, but incredibly impactful, moments in time. 

After all, the magic of a shooting star is not how long it lasts, but how breathtaking it is for the few brief moments it streaks across the sky.

Christopher Pierznik is the worst-selling author of nine books. His work has appeared on XXL, Cuepoint, Business Insider, The Cauldron, Fatherly, Hip Hop Golden Age, and many more. Connect on Facebook or Twitter. Please feel free to get in touch at


By Christopher Pierznik

Christopher Pierznik is the author of 9 books and has contributed to numerous websites on a variety of topics including music, sports, movies, TV, personal finance, and life. He works in corporate finance and lives in northern New Jersey with his family. His dream is to one day be a member of the Wu-Tang Clan.

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s