He'd climbed rap's commercial ladder in the 1980s; going from Doug E. Fresh's cohort MC Ricky D with two star-making showcases in "The Show" and "Ladi Dadi," to Def Jam's platinum-selling storyteller du jour Slick Rick, a silver-tongued rhymer with a knack for dark humor. In 1988, he dropped The Great Adventures Of Slick Rick, widely hailed as one of the greatest rap albums ever made.

The album set Rick amongst the biggest and brightest in Hip-Hop, primed to carry Def Jam into the 1990s alongside contemporaries like Public Enemy, EPMD and 3rd Bass. 

By 1990, Slick Rick was riding high. With a penchant for flossing, Rick was reveling in success. The British-born rapper became known for his massive gold jewelry and no shortage of ego, but his mother and manager suggested he get some protection. She hired Rick's cousin Mark Plummer to be his bodyguard, which seemed like a savvy move--until Plummer began extortion attempts both her and Rick. The rap star fired Plummer, who responded by threatening to kill Rick and his mother. 

So after Rick's Pathfinder was riddled with bullets outside a Bronx nightclub, the rapper decided to arm himself and go on the offensive. Rick began preparing for anything--riding in his car with weapons that included two machine pistols and a shotgun. And one day, after learning that Plummer on his block, Slick Rick opened fire. A bystander was struck and Rick sped off before crashing into a tree. Following his subsequent arrest, Ricky Walters was charged with two counts of attempted murder. 

“I was driving a rent-a-car Dodge Shadow at East 241st Street and White Plains Road when I saw my cousin Mark,” Walters told the cops at the time. “I drove home with my girlfriend, Lisa Santiago, and picked up six weapons: two .25-caliber automatic pistols, one .380, two Uzis, and one shotgun. I drove back to East 241st and White Plains, saw my cousin Mark, and shot at him about five times with my .380…. I left the scene westbound on 241st Street and got on the Bronx River Parkway going south. The police were chasing me. I tried to get off at the Allerton Avenue exit, couldn’t make the turn, and crashed.”

The Hip-Hop industry was waiting for his sophomore album, not to mention the fact that he was contractually obligated to deliver one to his label, Def Jam. 

The result of Rick's high-intensity recording is a flawed-but-uniquely-gripping album that furthers Rick's greatest storyteller" rep while also highlighting a staggering transformation in both his flow and his less-heralded vision as a producer.

“He’d be calling me, telling me to get this and that beat," Vance explained to SPIN in 1991. "I’d call him back and play it, and he’d kick it in his head to make sure they were flowin’. That’s how we did a lot of the new album.” Def Jam posted Rick's bail, and after the star pleaded guilty on March 22, he had until June 6 to do record. Rick went to Chung King Studios in Manhattan and rush recorded music, while also making the time to quickly shoot music videos for the project.

Lead single "I Shouldn't Have Done It" is a striking story song, with a title that seems to cheekily reference Rick's real-life woes. The actual song is about infidelity, as Rick explains how insecurities can self-destruct a relationship. It's one of Rick's most breezily insightful songs with a dark ending that's pure Slick Rick. 

"It's A Boy," also a single, is yet another foray into the trials and tribulations of relationships, but this time the focus is fatherhood. The accompanying video is one of Rick's funniest, featuring Rick's contemporaries from Chuck D and Flavor Flav to LL COOL J as kids in a romper room. 

So many tracks on the album have single-word titles, another indicator that everyone was speeding through the project. Album opener "King" features some of Rick's nimblest rhymes over a Bomb Squad-esque production from Rick and co-producer Vance Wright. On "Bond," Rick flips the Chi-Lites and Rufus Thomas as he plays international man of mystery, one of his most uniquely entertaining story raps.

"Tonto" is a darkly comedic semi-sequel to 1988s "Indian Girl (An Adult Story)" that furthers that song's jokey raunch; and the uptempo "Venus" features some of his best crooning, which was always somewhere between sincere and cynical. But Rick serves himself well on the hook, and against the piano-driven production, it's one of the album's best cuts. As is "Runaway," a top-tier Rick tale about (again) infidelity, but Rick's unique wordplay obscures whether he's happy or sad about his girl gettin' it in.

On almost every track, Rick adopts a speedy delivery only hinted at on his hit debut; breathlessly delivering quips and narratives as though a clock is ticking on the entire project.

In many ways, it was.

“It depends how you look back on yourself,” Rick would say to The Guardian in 2016 when asked to look back on the hardship of that time and his decisions. “If you overly scrutinize yourself, you could say: ‘I should have done this or that.’ You can look back and see how certain things influenced you to make wrong decisions. But you learn from your mistakes; what doesn’t kill you makes you stronger. You learn from your prison time, your bad and good situations. It’s like the story of Van Gogh with the ear-cutting-off: it depends on how you look at something.”

Slick Rick would drop another album while incarcerated, the pointedly titled Behind Bars before his release in late 1996. Alongside high profile collaborations with artists like OutKast, Aaliyah and Kid Capri, he released his first post-prison album The Art of Storytelling to critical acclaim in 1999. He hasn't dropped a long player in the over 20 years since, but Slick Rick has maintained a steady presence via live performing, singles and guest appearances. He's forever revered as one of the most gifted rhymers to ever touch a mic, and his sophomore album, while less heralded than his iconic debut, is more evidence that the Ruler's rep is well-earned. 

Rick told Wonderland in 2019: