Most Underrated Rappers: All-Time
When it comes to verbosity, stamina, longevity, stepping outside-of-the-box, and straight up overall rap skill, these legends take the cake for my most underrated spitters of all-time. Upon reading these takes, I hope you dig into these guys’ discographies to find gold and a section of the genre you didn’t know you were obsessed with. Here is the brief lowdown from my subjective taste:
When it comes to Philadelphia… please, you ain’t fucking with no amateurs, homie - Philly ain’t known for cheesesteak sandwiches only. Philly is the origin city of the legendary 90’s rap group The Roots. But I’m not getting into the ever-flowing top 10 group - I’m talking about their frontman, Black Thought. Thought has been on an absolute microphone tear since his flaming 10 minute freestyle on HOT 97 with Funkmaster Flex in 2017, followed by 2018’s Streams of Thought Vol 1, and a handful of other thought-provoking projects laced with sharp awareness. You may only know him from The Tonight Show Starring Jimmy Fallon, but he has steadily been one of the most skilled rappers in hip-hop since The Roots’ 1993 Organix and their classic from 1996, Illadelph Halflife. To get the full idea, listen to his 2022 album Cheat Codes which he had been working on with Danger Mouse since 2006. You very well may see this project in our Top 10 Albums from 2022, as this album is at the pinnacle.
Westside Lu. Madison and Homan. Chicago’s very own Lupe Fiasco has put out everything from ageless radio hits “Kick, Push” (2006), “Superstar” (2007), “The Show Goes On” (2011), to the greatest showcase of lyrical ability ever heard, possibly my favorite rap song ever, “Mural” (2015). Lupe burst onto the scene with a feature on fellow Chi-Town artist Kanye West’s “Touch the Sky” (2005) which he followed up with two classics, Food & Liquor (2006) and Lupe Fiasco’s The Cool (2007). Since those popular releases, he has put out a handful of radio hits, but more importantly, some lesser known albums displaying some of the best lyricism in rap history. He is so good at writing words and surprising you with them that he is currently teaching a Rap Theory course at MIT. To get the bigger picture, listen to Lupe’s latest release, Drill Music In Zion (2022). You’ll also see this one in our Top 10 Albums of 2022.
Hailing from the D, Royce da 5’9 has been one of the most impressive rappers since he appeared on “Bad Meets Evil” off Eminem’s debut album Slim Shady LP (1999) and a few other songs with Eminem that year. He has been one of the best lyricists since he became known and would probably be a bigger deal if it wasn’t for his beef with D12 in the early 2000s when Detroit was popping off, but he has been respected by your favorite rappers even if you didn’t know him. With over 20 years of top tier rap performances, some of my favorite include the collab albums Hell: The Sequel (2011) by Bad Meets Evil in which Royce is one half with Eminem, PRhyme (2014) and PRhyme 2 (2018) by PRhyme in which he is the mic half and DJ Premier is behind the wheelz of steel, and the solo albums Book of Ryan (2018), and The Allegory (2020). He is so damn good at rapping. For quick evidence, check out his 2017 freestyle “Beats Keep Calling”, in which he demolishes samples of “Bad and Boujee” and “Lockjaw”.
Last rapper I’m going to list is the underground legend Aesop Rock. This dude has one of the most interesting imaginations in all of rap, and has had so since his debut Music for Earthworms (1997). He was front of the line during the late ‘90s-early ‘00s wave of New York underground, releasing numerous albums from 1999-2007 with El-P’s Definitive Jux label. After a hiatus and a few smaller projects, Aesop came bursting back like he was a Webster’s Dictionary on DMT and adderall with 2016’s The Impossible Kid. I see it as one of the greatest underground albums ever released. Another notable project of his is Malibu Ken (2019)... one of the zaniest yet beautifully colorful albums in recent memory. Spirit World Field Guide (2020) is another display of his lyrical ability, coated with cadences that will surprise you every verse. He is difficult to get into due to being extremely verbose, but once you’re in - the lyrics and imagery will hold you there. Check out Garbology (2021) for his most recent mind-bending album and also the late 2022 single “Pumpkin Seeds” ft. Lupe Fiasco, fellow most underrated rapper of all-time. Potential Top 10 Single of 2022? Most definitely.