Jam Sesh with Kevin, Vol. 5

MAY 2025: Underrated '90s hip-hop albums

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It seems safe to say, at this point, that the retrospectively rather quaint debate over which albums belong in the ‘90s hip-hop canon has been settled. But with those colossally expected answers comes a whole bunch of new questions about whether this list is complete, or if there are a broader range of LPs that belong in this equation. This month,

Kevin Alexander

and I make our respective cases for ‘90s hip-hop albums that may not be underrated by hip-hop heads, but they are definitely underrated in the sense that the broader public should recognize these gems as among the greatest albums of that decade. Sure, they may not be in the same tier as your Illmatics or your 36 Chambers—well, most albums aren’t…—but they are heavy hitters in their own right and should be recognized and discussed as such.

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MY PICK: Lifestylez ov da Poor & Dangerous - Big L

Big L had flows, punchlines, cadence, delivery—the kind that even an emcee like Nas said he was scared to death of. He was the first rapper who made me fall in love with the technical and creative side of lyricism. In high school, when I first heard the line, “Ask Beavis, I get nothing butt head,” it shattered my adolescent mind. A master of the lyrical stickup, Big L could just ride a beat and undress his competition with kinetic metaphors and a brash comedic repertoire. Lifestyles is gritty horrorcore with impeccable boom-bap production, and is a must-listen for anyone getting into ‘90s East Coast hip-hop. Big L is one of the biggest “what ifs” in the genre, a huge loss an a generational talent who was taken from us before he even really got started.

Highlights: Put it On, 8 Iz Enuff, All Black, Da Graveyard, Street Struck, Let ‘Em Have It “L”

KEVIN’S PICK: ‘93 ‘Til Infinity - Souls of Mischief

My Response:

This was one of my runner-ups, so ‘93 ‘til Infinity has my seal of approval. Have you ever seen certain ‘90s cartoons or movies where twins would finish each other’s sentences? Souls of Mischief are sort of like that, and this is an example of a great album coming out of friends shooting the shit over the beats with great wordplay. This is probably the most East Coast that a West Coast album could sound like. They remind me of a Bay Area version of A Tribe Called Quest, as they actively aspire to their fluidity, effortless flows, and telepathic trade-offs. The transitions are seamless, tracks often segue into each other without pause, and the title track is a timeless classic. This is a GOATed West Coast hip-hop album.

Highlights: Live and Let Live, What a Way to Go Out, Never No More, ‘93 ‘Til Infinity, Anything Can Happen, Batting Practice

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MY PICK: Ridin’ Dirty - UGK

As much praise as this album gets, it still deserves more. Outside of prime OutKast, Ridin’ Dirty goes toe-to-toe with the best of any Dirty South album. Pimp C was the soul, Bun B was the attitude. “One Day” blew me away with its smooth production and somber lyrics. The rest of the album isn’t as melodic, but Bun’s verse on “Murder” is a thunderbolt to the forehead, then the transitions to the ultra-funky “Pinky Ring” are incredibly smooth and laid back. This is the perfect fusion of funk, soul, and gospel-infused sounds. You cannot tell the story of how southern trap music was born without talking about Ridin’ Dirty.

Highlights: One Day, Murder, Pinky Ring, Diamonds & Wood, 3 in the Mornin’, Hi Life, Ridin’ Dirty

KEVIN’S PICK: Bizarre Ride II The Pharcyde - The Pharcyde

My Response:

The mind meld with Kevin is strong this month, as this was another runner-up of mine. When West Coast hip-hop was influenced by N.W.A. and G-Funk, the Pharcyde was taking their cues from De La Soul and Leaders of the New School with their fusion of punchy rhythms, loopy rhymes, soulful pianos and organs, and head-nodding baselines. Bizarre Ride is a freewheeling hip-hop cabaret, an unholy amalgam and simultaneous parody of Black entertainers. The Pharcyde are deeply unconventional and deeply stupid in the best possible way, and they rap as if they’re a vocal harmony group who learned how to talk instead of sing. The result is a sonic utopia. This is a light record, breezy and funky, but it’s not lightweight—it’s hard-hitting, but done in a way that creates a world that’s riotously funny, twisted, and brooding with noir-ish cool

Highlights: Oh Shit, Soul Flower (Remix), Ya Mama, Passin’ Me By, Otha Fish

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MY PICK: De La Soul is Dead - De La Soul

As much as I love 3 Feet High and Rising, De La Soul’s first four albums are all classics, and they’re all on par with each other. The skits are even wilder, and the samples Prince Paul uses are so left-field. I appreciate the storybook concept, and the group came more into their sound on this one. “Keepin’ the Faith” shines as a great culmination of their progression, and jams like “Saturdays” continue the uber-positive vibes of their debut. Their experience in the music industry gives more bite to their humor, as De La isn’t afraid to go dark and personal. Even as Pos divulges his brother’s drug addiction, the inventiveness of the sounds and rhymes keeps everything interesting, if not outright fun to listen to. Don’t let 3 Feet High and Rising overshadow De La’s subsequent albums—this is about as consistent of a discography as you’ll find in hip-hop.

Highlights: Oodles of O’s, A Roller Skating Jam Named “Saturdays,” Bitties in the BK Lounge, My Brother’s a Basehead, Let, Let Me In, Millie Pulled A Pistol On Santa, Who Do U Worship?, Pass the Plugs, Fanatic of the B Word, Keepin’ the Faith

KEVIN’S PICK: So...How's Your Girl? - Handsome Boy Modeling School

My Response:

Kevin’s third pick nailed the theme (at least for me) because as steeped as I am in ‘90s hip-hop, I’ve never come across this album. Considering this dropped in 1999, the production feels very modern. It’s a surprisingly cohesive listen, even if the production on almost every song, not to mention the featured vocalists, is completely distinct. Like a good drink, this is inventive, funny, and strong. This is a wonderfully refreshing listen, filled with quirky instrumentals and textured raps that satirize upper-class snobbery and vain materialism.

Highlights: Magnetizing, Waterworld, The Truth, Sunshine, Megaton B - Boy 2000

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That’s it for the May 2025 edition of Jam Sesh! Let us know what you think about our picks in the comments.

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Jam Sesh with Kevin, Vol. 4

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