MF DOOM’s Operation: Doomsday came to the surface 20 years ago today, on April 20, 1999. Birthed out of tragedy and commercial frustrations, Metal Face DOOM, real name Daniel Dumile, created a solo album shrouded in mystery, multi-syllabic rhymes, and technically rough, back-to-the-future production. The display was weird, cartoonish, and wild at a time when Rap music in the mainstream was taking itself very seriously. Although whimsical in its form, DOOM’s album dealt with tremendous pain, industry marginalization, and an MC building a pathway to reinvention and the brightest of futures. It marked a turning point toward a new era of Underground Hip-Hop, by a man more concerned with shedding his old skin than staying in the convention of his Rap contemporaries.

Of course, Operation: Doomsday could not exist without the intent of rebirth, and unfortunately, real death and despair was a catalyst for that purpose. Prior to the record’s release, Dumile was rapping as the Afrocentric Zev Love X, one-third of the group KMD, alongside his younger brother DJ Subroc, and friend Onyx The Birthstone Kid. After KMD found success and signed to Elektra Records, the group dropped video single “Peachfuzz,” and soon after, the imaginative 1991 full-length LP, Mr. Hood.

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With Onyx leaving the fold in the early ’90s, and X and his brother Subroc got to work on their major label follow-up, Black Bastards. The two reportedly spent months grabbing samples, writing rhymes and tweaking productions in various studios across New York to work on the record. But on April 23, 1993, Subroc was struck and killed by an oncoming car while trying to cross the Long Island Expressway on foot. Zev Love X was left to finish the small remainder of the album without his brother and band-mate.

Black Bastards was initially scheduled to release on May 3, 1994, but due to the album’s controversial artwork of a “Sambo” figure being lynched, the record was ultimately shelved a month before hitting stores, thanks in large part to push-back from the press, including Billboard‘s Terri Rossi and Havelock Nelson. Zev Love X had created the album artwork himself, aiming to “execute the stereotype” established by whites, rather than depicting a lynching. “It’s not the hanging of a person,” Dumile told Jon Shecter, founding editor of The Source magazine, for an article titled “Corporate Hysteria.” “It’s an idea being executed –– the whole concept and stereotype of our people being displayed as minstrels or servants or fools.” Even with the Jody Watley-sampling “What A Ni**a Know?” serviced as a single, and a few promo copies of the full-length already in circulation, much damage was caused with KMD’s label relationship. Elektra walked away from the group which had devolved to Zev Love X.

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Failing to release the album he had worked on for years, his brother’s final act, Dumile took a hiatus from rapping and used his time to mourn. He was broke, pissed off. He moved down to live with family Georgia and re-calibrate his mind. During this period, the artist who had grown up on Long Island also made frequent up-north-trips to the Big Apple. Dumile was “damn near homeless, walking the streets of Manhattan, sleeping on benches and sh*t,” according to an interview with The Wire magazine in 2005.

In 1995, at the suggestion of friend and Rap peer Kurious, Daniel Dumile chopped it up with radio host, A&R, and Hip-Hop conduit Bobbito Garcia to show him what a post-Zev Love X sounded like. While away from the industry, Dumile had reinvented himself during his hiding as MF DOOM, a super-villain rapper with a more laid-back flow than Zev Love X ever had, maintaining the same charisma. His rapping turned from easy-going to chaotic, with even more buttery flows. He rapped with precise attention, intentionally tripping over his off-kilter production. DOOM built upon KMD’s later sound with an expanded universe of ’70s Saturday morning cartoons, nickel bags, and scuffed-up ’70s Jazz and Rock breaks.

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Before resurfacing in the Hip-Hop scene, Daniel Dumile used a mask to hide his face, representing a turn away from Zev Love X, and showing the world what the new face of Daniel Dumile looked like. DOOM explained drawing inspiration from old comic books to The Wire: “The way comics are written shows you the duality of things, how the bad guy ain’t really a bad guy if you look at it from his perspective. Through that style of writing, I was kinda like, if I flip that into Hip-Hop, that’s something ni**as ain’t done yet. I was looking for an angle that would be brand new. That’s when I came up with the character and worked out the kinks—that’s the villain.”

It was Bobbito that would help Dumile surface back onto the scene as MF DOOM via his Fondle ‘Em Records imprint. In 1997, “Dead Bent / Gas Drawls / Hey!” was released on 12″ vinyl. The singles were recorded at DJ Stretch Armstrong’s house, Bobbito’s radio co-host at WKCR. In 1998, Dumile appeared at an open mic poetry session at New York’s Nuyorican Poets’ Cafe. In those early days, he reportedly masked his face (using anything he could, including a sock, or his infamous metal-face mask) and performed as MF DOOM. Within the next year, on April 20, 1999, Fondle ‘Em Records released the MC/producer’s solo/debut, Operation: Doomsday.

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The record kicks off with “The Time We Faced Doom (Skit),” a retro-tinged theme song, weaving a sample of dialogue from the 1983 movie Wild Style together with a robotic voice announcing an important “Flash Message Top Secret Ultra.” The robot delivers lines in a manner reminiscent of Sidney Sheldon’s 1991 novel, The Doomsday Conspiracy. The robotic transmission called for the album’s cohorts to assemble: “Notify MF, KMD, GYP, CM. Effective Immediately.” The latter half of the track samples dialogue from the original 1967 Fantastic Four TV series, with “Mr. Fantastic” stating: “Doom hates us all, but in his warped mind, he has a personal score to settle with me.”

Of course, the record doesn’t truly kick off until DOOM’s sample flips of “Kiss Of Life” by Sade and “Poetry” by Boogie Down Productions play on “Doomsday.” It’s here that listeners first hear DOOM’s complex rhyme schemes and odd slang references within the first four bars of the song: “I used to cop a lot / But never copped no drop ? Hold mics like pony tails tied in bobbalobs / Stop and stick around, come through and dig the sound / Of the fly, brown 6-0 sicko psycho who throws his d*ck around.”

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But the next song, “Rhymes Like Dimes,” provides the ultimate DOOM definition and Operation: Doomsday imperative. DOOM raps: “Only in America could you find a way to earn a healthy buck / And still keep your attitude on self-destruct.” The juxtaposition of Dumile’s point in his career as DOOM, versus what he left behind as Zev Love X, and the tragedy of events that led to DOOM’s inception, feed into these ideas of turning into a villain well. It also shows that in his multi-syllabic rhyme symmetry, the MC dropped heavy jewels in his points.

DOOM brings up Subroc’s name throughout the project, while Fantastic Four samples and themes of villainy pop up at every opportunity available to Dumile. Bars are spit in a stumbling, yet hasty fashion. They often reference cultural artifacts lost by time. On “Gas Drawls”, DOOM details his dedication to Rap after his brother’s death: “To my brother Subroc and Black Ju’ / I crack brew for, two more, three men, two up / I hit the brew up like nobody knows, how X the unseen feels / When giving crews a brush with death like between meals.” As DOOM revealed a few weeks ago while celebrating another album birthday (2004’s Madvillainy), he treats writing rhymes, not unlike Scrabble. Operation Doomsday fills the board with triple-word scores that use the most challenging letters.

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“Tick, Tick…” showcases DOOM’s sampling tastes, choosing to flip a section of The Beatles’ track “Glass Onion,” for a see-sawing solo track by then-Kool G Rap affiliate, MF Grimm. The samples on Operation: Doomsday delve into the obscure and then-unpopular choices by rappers, from the eerie and pestering high-pitched Scooby Doo sample on “Hey!” to Steely Dan and ’80s Funk grooves. Although DOOM’s various rhyme styles and bars are cited as his greatest asset, his production is equally unique. Both talents have influenced troops of copycats since.

The entire super-villain experience concludes with “?”, where DOOM chronicles his tales of KMD and records his thoughts on the death of his brother on wax. Instead of questioning the painful events of the last six years, he embraces them as giving him an answer. “You out your frame but still bagging ’em too / You know I know, these hoes be asking me if I’m you / Like my twin brother, we did everything together / From hundred raka’at salats to copping butter leathers / Remember when you went and got the dark blue Ballys / I had all the different color Cazals and Gazelles / The ‘SUBROC’ three-finger ring with the ruby in the ‘O,’ ahk / Truly the illest dynamic duo on the whole block / I keep a flick of you with the machete sword in your hand / Everything is going according to plan man.”

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To this day, Operation: Doomsday is one of Hip-Hop’s greatest examples of reinvention. On a shoestring budget, under the worst of circumstances, DOOM returned to Rap as a villain with a masked identity and a sinister sound. However, instead of snatching jewels, he dropped them.