Explore the best hip-hop concept albums of 1999 featuring standout releases with unique themes and narratives. Covering everything from personal stories and fictional worlds to cultural commentary and deeper explorations of society, these are the albums that stood out among the year's conceptual releases.

5-Star Albums

Prince Paul – A Prince Among Thieves

Prince Paul’s A Prince Among Thieves is a concept album that follows Tariq, a young, ambitious rapper trying to raise $1,000 to record a demo tape for an important meeting with RZA. Struggling to make ends meet, Tariq quits his low-paying job and turns to his childhood friend True, a seasoned hustler, for help. True introduces Tariq to the drug game, promising it will be an easy way to make the money he needs. As they dive deeper into the criminal underworld, Tariq encounters a colorful cast of characters, including corrupt preachers, unstable arms dealers, and shady pimps. Along the way, his journey is fraught with danger, and a police ambush that lands him in jail. Tariq pushes forward, driven by his dream, only to face betrayal in a final, deadly showdown that underscores the price of desperation.

4.5-Star Albums

Mos Def – Black on Both Sides

Mos Def’s Black on Both Sides is a statement about Black identity, culture, and societal perceptions. With this album, he tackles stereotypes, challenges misconceptions, and highlights the complexity and depth of Black experiences. “It’s a collection of songs designed to relay a theme and a message about Black people in the world. I have to do that. Because there’s so much propaganda that exists about who we are, what’s important to us, our abilities. I did it to dispel a lot of the myths that exist about hip-hop, about Black culture, about Black society, about our sensitivity to politics, our level of awareness.” – Mos Def

4-Star Albums

Blackalicious – Nia

Nia is the name of the fifth principle of the African-American holiday Kwanzaa and the Swahili word for “purpose”. The album as a whole is about Gab and Blackalicious taking a look at the wrongs within the world and finding their purpose.

Handsome Boy Modeling School – So… How’s Your Girl?

So… How’s Your Girl? is an album ostensibly organized by two fictional boozy dilettantes, Nathaniel Merriweather (in actuality, producer Dan the Automator) and Chest Rockwell (Prince Paul), who are two geeky producers masquerading as jet-set male models centered around the musical curriculum of a men’s modeling school. All this in turn is (loosely) based on a subplot from Chris Elliott’s short-lived Get A Life television series, which is sampled throughout to provide some of the continuity for the album  

MF DOOM – Operation: Doomsday

Operation: Doomsday chronicles the story of DOOM, a young college student turned Diabolical Mastermind after a scientific accident scarred his face. The backstory of Operation: Doomsday is similar to that of Marvel Comics supervillain Dr. DOOM, with a series of terrible setbacks and tragedy culminating in the birth of a villainous persona. After suffering the devastating death of his brother and the dropping of his group from their record label, MF DOOM, formerly known as Zev Love X, was left emotionally scarred. His lingering pain manifested in the form of a masked hip-hop supervillain who wishes to rule the world for its own good on Operation: Doomsday.

The Roots – Things Fall Apart

Things Fall Apart is inspired by Chinua Achebe’s 1958 novel of the same name, which explores the collapse of traditional African societies under colonial rule. The title serves as a metaphor for the struggles and disintegration within modern society in the context of black experiences. The album dives into themes of systemic oppression, personal and societal breakdown, and the search for identity and resilience in the face of adversity. The album cover, featuring a black-and-white photo of a couple running during the 1960s Civil Rights Movement, underscores these themes.  

3.5-Star Albums

Kool Keith – Black Elvis / Lost in Space

Kool Keith’s album Black Elvis / Lost in Space covers two different, but intersecting concepts, one about Black Elvis who professes to live a futuristic lifestyle while other wannabe pop stars are trapped in the past, while the other is a story about being lost in space.  

Phoenix Orion – Zimulated Experiencez

Zimulated Experiencez is an amalgamation of tales based on a variety of cartoons, comic books, movies, and some of Orion’s very own creations. Often uses samples from old sci-fi movies or tv shows. With samples from old sci-fi films and TV shows, the album weaves tightly wound, self-contained stories that showcase Orion’s imaginative storytelling as he juggles all the characters. 

Slick Rick – The Art Of Storytelling

The Art of Storytelling is basically Slick Rick flexing his storytelling skills in every way imaginable. Each track tells a different story, as Slick Rick shows off his abilities and lays down why he thinks he is the greatest storyteller in rap. He bounces between funny, wild tales and more personal reflections, keeping it all sharp with his signature wit and flow. 

Honorable Mentions

• Cypress Hill – Los Grandes Éxitos en Español
• DJ Frane – Frane’s Fantastic Boat Ride
• Dr. Dooom – First Come, First Served
• Ithaka – Stellafly
• L*Roneous – Imaginarium
• Scotty Hard – Return of Kill Dog E
• Sporty Thievz – Street Cinema