72. Black Milk, Tronic
Fat Beats
Released October 28, 2008

While Black Milk’s past work (including 2007’s Popular Demand) hewed to typical Okayplayer backpacker styles established by Madlib and 9^th Wonder, he finally found his voice with Tronic. On the surface, the album is reminiscent of the late J Dilla, from the classic Detroit “tronic” tones to the slumping pace. But Black Milk smartly distinguishes himself with analog instruments, pumping out “live” tracks from the swooping horns and crackling drums of “Give the Drummer Sum” to the sampling keyboards of “The Matrix,” the latter a deadly session between himself, Pharoahe Monch and Sean Price, with DJ cuts courtesy of Premier. He drew some criticism for his stilted raps, which dragged underneath the beats. At the same time, his unorthodox rhymes give Tronic an off-the-cuff tone – you can hear him putting his heart into the music. He’s not just making beats for beats’ sake.

78. The Cool Kids, The Bake Sale
Chocolate Industries
Released May 20, 2008

The Bake Sale was the closing of a first chapter in the Cool Kids’ career. Most of its tracks had already circulated around the Internet, catapulting the Cool Kids — Mikey Rocks and Chuck Inglish — into notoriety. Songs such as “One, Two,” where Mikey Rocks percussively looped a girl lolling “da da da da,” were modest, minimalist wonders. Even if Mikey Rocks mostly borrowed bass styles from other regions for his Chicago coolness – the booty bass codes of deep South towns like Miami and Atlanta and the pre-rugged noise of mid-80s golden age New York – he mixes his influences into a uniquely middle-class vision: the freewheeling hipster consumerism of “Gold and a Pager” and “A Little Bit Cooler.” Aspiring to old-school glory, the Cool Kids couldn’t muster the fly rhymes that typified those old-school classics. Instead, they produced a new kind of classic with The Bake Sale, one both informed and unencumbered by the past.

81. Kid Cudi, A Kid Named Cudi
Online mixtape
Released July 2008

Mixtapes are by nature vocal showcases built on freestyles over familiar beats, a handful of original songs, and plenty of shout-outs to famous mentors and friends, as if to foment success by association. Intangibles such as song concepts and memorable personalities separate the wheat from the chaff. Kid Cudi’s breakout mixtape excels on all fronts. He flaunts the monotone crooning that made his debut single “Day ‘N Nite” a top 5 Billboard smash in the summer of 2009. But he doesn’t overdo it. Flat raps over Dilla beats (“Cudi Gets”) and straight-up singing over Paul Simon’s “50 Ways to Leave Your Lover” (reinterpreted as “50 Ways to Make a Record”) bring variety to his stoned harmonizing. He declares his himself a loner (“Man on the Moon”), but wants our love badly, and pleads for it (“Embrace the Martian”). In the result, he exemplifies the blog-rap era and its thousands of voices, pumped up by MySpace and rap blogs, declaring themselves as unique voices waiting to be discovered.

82. Flying Lotus, 1983
Plug Research
Released October 3, 2006

Born Steven Ellison and a nephew of Alice Coltrane, Flying Lotus appeared in random spots before 1983: a beat for Adult Swim here, a Mia Doi Todd remix there. And the luminous cluster burst that was his debut resembled other phenomena: the romantic indulgences of Daedelus (who contributes a hopped-up remix of the title track), the vocal chops and edits of Scott Herren, and the breakbeat soul of Madlib, Jay Dee and many others. But his vision was original. The “Space is the Place” vibe of the opening title track unfolded into “São Paolo,” a series of handclaps syncopated into percussive funk. The minute-long “Bad Actors,” a backhanded homage to Lotus’ native L.A., morphs into “Pet Monster Shotglass” and an unfocused stutter-step. There is the final epiphany of “Untitled #7” and its soft, synthetic patter, the psychedelic ballad “Unexpected Delight” (voiced by Daedelus’ partner Laura Darlington), and the Daedelus remix. That’s eleven songs, 33 minutes, and one mostly instrumental journey into laptop metaphysics.

83. Cormega, The Realness
Legal Hustle/Landspeed Records
Released July 24, 2001

Cormega’s debut arrived during a moment of reconciliation between the oppositional worlds of underground and mainstream rap. The Realness was distributed by Boston-based Landspeed Records, an indie distributor known for Premier-leaning hip-hop; its success would encourage Landspeed to indulge in so much Queensbridge-Infamous Mobb records that the company cleaved in two (out of which the backpack-friendly Traffic Distribution was formed). And The Realness’ status as an album borne from the ashes of a shelved Def Jam debut (The Testament, which was finally released independently in 2005) endeared it to a growing cult of New York street rap collectors. Cormega’s appeal lies in his plainspoken voice. “R U My Nigga’s” asks, “If I die, would you cry/Need, would you provide/If I got heat, would you be squeezing side by side?” “Fallen Soldiers” shouts out fellow crooks, asking, “Did you ever lose a nigga to love/Then ask yourself is there a heaven for thugs?” He’s not a technician, and won’t dazzle you with his verbal dexterity. The Realness is simple stuff, really, but its themes of brotherhood and broken bonds make for a compelling drama.

85. Prodigy, Return of the Mac
Koch
Released March 27, 2007

On Return of the Mac, Prodigy plays the role of superthug. The Alchemist produces a context for his mannerisms, liberally lifting from 70s and 80s classics such as James Brown’s “Down and Out in New York City.” He conjures a mood that’s perfect for Prodigy’s ominous threats and proclamations. When Prodigy says, “I sit alone in my dirty-ass room staring at candles, high on drugs,” paying homage to the Geto Boys’ “Mind Playing Tricks On Me,” he really sounds paranoid, “scheming on you niggas.” Wisely, Koch Records marketed this self-described “mixtape” as a new album, helping the Queensbridge rapper garner some of the best reviews of his career. But it would be for naught: Shortly after Return of the Mac’s release, Prodigy was sentenced to three years in prison on gun possession charges. He now languishes at Marcy Correctional Facility in Oneida County, New York, and is scheduled for release in 2011.

88. Tanya Morgan, Moonlighting
Loud Minority Music
Released April 4, 2006

In the Okayplayer-led world of soulful, classically inspired hip hop, Tanya Morgan’s debut marked a transition from the Little Brother styles of the mid-00s to the freewheeling blog rap of the present day. Hailing from Cincinnati (Donwill and Ilyas) and Brooklyn (Von Pea), the three rappers stuffed Moonlighting with goofy, hastily written songs (Ilyas complains about people mistaking him for Bob Marley on “Just ‘Cause I Got Locks”), Von Pea’s zippy beat-making techniques (sampling MC Lyte on “Paper Thin,” looping Marvin Gaye on “Want U To Want Me”), and a murky hiss that represented their modest, subterranean origins. Despite the album’s poor sound quality, the group’s infectious songs were clearly audible. As the group’s label/management Loud Minority Music struggled to distribute Moonlighting (the label would eventually reform as Interdependent Media), most discovered it via Internet downloads and enthusiastic reviews. The resulting acclaim cemented Tanya Morgan’s status as leaders of the new school.

89. People Under the Stairs, O.S.T.
Om Records
Released June 4, 2002

First emerging in 1998 amidst an L.A. indie explosion led by Dilated Peoples, Jurassic 5 and the Lootpack, People Under the Stairs were the scrubs of the bunch. But producer/rapper Thes One and DJ/rapper Double-K’s self-released 1998 debut, The Next Step, expressed a simplicity and charm that sometimes eluded their bigger rivals. Keenly aware of their underrated status, PUTS upped the ante on O.S.T.’s “The Outrage,” calling out Madlib (“Fuck a loop digga, in my city man just stay home”) and influential journalist Oliver Wang (“Oliver ‘Mark Ass’ Twang”). It permanently marked the group as scene outsiders.

Still, O.S.T. is an excellent reason for why the group continues to thrive. Its best tracks offer slices of Los Angeles life over funky soul breaks. “The Suite for Beaver Part 1” fleshes out a Friday night escapade with allusions to “one of those weeks stressing frequently” and “I felt no worries as I slid out south to Crenshaw Heights.” “Acid Raindrops,” a fan favorite, celebrates the ruminative powers of weed with poignancy. PUTS sound and look so much like their backpack audience that it’s easy to forget how difficult it is to make dope hip hop.

91. Mr. Lif, Enters the Colossus
Definitive Jux
Released November 28, 2000

A veteran of the East Coast battle rap scene, Jeffrey “Lif” Haynes’ loquacious rhymes hewed to the “super-scientifical” style – coined after a phrase in Jeru the Damaja’s “Can’t Stop the Prophet” – and rendered songs with purplish language. On “Datablend” he raps, “First I unleash my rage on the stage/Off the top of the dome, fuck the written page/Then engage in telekinesis thesis/Which verbally rips your bitch-ass squad to pieces.” But Mr. Lif has less bloody interests, too, as he works through each misty, dramatic track as if freestyling after a smoke-out session. On “Front On This,” he rhymes, “It’ll give courage to cowards/And put a stop to homicidal cops and watchtowers.” On future releases, Lif would break out of the Dungeons-and-Dragons alley of Enters the Colossus. But it may be the only Lif album that captures a particular moment in rap history, reflecting a scene that no longer exists.

87. Beanie Sigel, The Truth
Roc-A-Fella Records
Released February 29, 2000

These days, it seems improbable that Beanie Sigel, the oft-arrested, thematically-limited Vladtv.com star and indulger of corny beefs with other rap gangstas, was once considered a next-to-blow rookie. The Truth opens with Kanye West’s churchy organs (“The Truth”), then threads through keyboard presets from Swizz Beats, then heavy in his synthesizer Mozart phase (“Who Want What”), and Rockwilder’s ominous horn pumps on “Stop, Chill.” “Where I’m from, all my niggas from under the ground,” raps Beanie on the latter. “Rock jeans and a bunch of white tees/Troopers/They don’t post but they toast and they like to shoot you.” It’s as loud and violent as a street argument that turns into a tragic shooting. And Beanie’s East Coast slanguage, broken down in plain but vivid language, interprets it all. Like so many other once-hot newcomers, from David Banner to Jadakiss, Beanie has spent the rest of his career trying to convert The Truth into mainstream success with mixed results. But he can point to at least one album as a symbol of achievement.