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It’s that time of year again! Ghost, goblins, ghouls and all types of little people, and some grown folks, dressed up in their best and scariest get to indulge in the decadence and fright that comes along creeps up on us every year at the end of October.

Halloween is an interesting, somewhat polarizing, but nonetheless entertaining time of year. And Hip Hop is no stranger to dabbling in the dark side of life, with tons of songs and videos dedicated to bringing out some of the darkest sides of some of our favorite emcees.

And it’s not just the old school novelty songs like Whodini’s “The Freaks Come Out at Night”“The Addams Family” that take the cake.

Some of the most disturbing, subconsciously scary and bleakest music has come from Hip Hop from some of its most famous artists. So we at SoSoActive.com decided to take a brief look at 12 of the most frightening Hip Hop songs of all time. Just keep telling yourself it’s only a dream. Or, rather, it’s only music. (*Insert Vincent Price “Thriller” evil laugh here.)

“I Seen A Man Die”–Scarface: Earlier on in his career, Brad Jordan was infamous for being Hip Hop’s version of Alfred Hitchcock with cryptic Southern rhymes and an obsession with the afterlife. This song, from his 1994 album The Diary is his dark crowning achievement from that era.

“Dance with the Devil”–Immortal Technique: One of the more serious and topical songs on this list, this may very well be Technique’s most well-known single, detailing the story of Billy, a misguided young man craving social acceptance from his peers so much so that he is peer pressured into committing a series of vile acts of defiance, the most disturbing of which is when he unknowingly beats and rapes his own mother.

“The Crossroads” – Bone Thugs-N-Harmony: The seminal Hip Hop tune for coping with the loss of a loved one and pondering the afterlife. The 5-man Cleveland crew got extremely reflective on the track that was unofficially dedicated to Eazy E after his passing and earned them a Grammy nod.

“Bad Dreams” – Busta Rhymes: This entry from Busta is one of his more obscure pieces of work form his Genesis album, but is still pretty chilling. On it, Bussa Buss details a nightmare in which he goes toe to toe with Satan himself. Busta’s distorted, villainous voice serves as the Devil and really takes the track to a sinister level, creating the sense that one is really walking through Hades to come face to face with the most infamous fallen angel.

“Bad Meets Evil” – Eminem feat. Royce Da 5’9”: From Eminem’s monumental debut The Slim Shady LP, Em and Royce get super lyrical on a story of two emcee outlaws hell bent on doing whatever they please. The cowboy voice at the beginning and end may be a little corny but the two emcees monstrous rhymes more than make up for it on a track that juxtaposes between humorous and ominous.

“My Mind Playin’ Tricks On Me” – Geto Boys: A song that has clearly influenced the likes of Bone Thugs and Three Six Mafia, this is still as creepy as ever well over 20 years later. Scarface, Willie D and Bushwick Bill were unmatched in creating a haunting masterpiece that touched on mental illness, paranoia and our deepest fears. The greatest moment had to be Bushwick Bill punching the ever-loving crap out of the concrete at the end of the video.

“Interview With a Vampire” – Ras Kass: Deep throbbing bass line, introspective, inward-looking, complex lyricism, vocal distortion and a prevailing theme of good against evil and the light versus the dark makes Ras Kass’s song a true dark classic. More thought provoking than it is scary, this joint still raises many questions in the heads of many Hip Hop fans to this day.

“Yonkers” – Tyler The Creator: More so menacing and threatening in its pacing, production and musicality and not so much in the content, the song Tyler has become most famous for is no less ominous and troubling. And of course, Tyler’s signature raspy growl, coupled with the imagery in the video of him eating and throwing up a cockroach, is pure new millennium shock value at it’s finest.

“Tear The Club Up ’97” – Three Six Mafia: Arguably the Memphis, TN collective’s most beloved track, the group created a sound scape and an atmosphere on this song that was equal parts frightening and doom-filled, yet one that you could still bounce to in the club. The ski masks and scary, southern-style CGI graphics on the World Domination album cover only helped to cement this jam as a deceptively dark work of genius.

“Damien” – DMX: In 1998, there weren’t many rappers close to the level of darkness and sheer malice of Dark Man X. This tale from his debut, It’s Dark And Hell Is Hot, is basically the Hip Hop version of “The Devil And Tom Walker”, where X meets a figure he deems to be his guardian angel and swears to give his right hand in exchange for his success. The second installment from his follow-up album featured Marilyn Manson and was even more menacing. Both featured the classic dark hook, “The snake, the rat, the cat, the dog/ How you gonna see ‘em if you livin’ in the fog?”

“Closed Casket” – Esham: Considered by many the primary figure in Detroit acid rap, and also by his own admission, this is one of Esham’s darkest pieces of music from a long career of independent music success. Lyrics detailing him going to Hell, meeting the Grim Reaper and Satan, have curiously helped Esham carve out a niche to become the most successful independent artist in Detroit Hip Hop history.

“Demons” – Tech N9ne feat. Three Six Mafia: Two of the most shadowy but still misunderstood Hip Hop acts of all time connect on this joint from Tech Nina’s K.O.D. album. N9ne has always been an expert at baiting people into believing the many misconceptions about him, and “Demons” helps him to so to a tee.

Ron Grant is a freelance journalist and blogger originally from Detroit and currently residing in Orlando. He is a contributor at HipHopDX.com, is the lead writer for Orlando-based indie music label Conscious Mind Records and runs his own independent music blog, The Music Nerdvocate. Follow him on Twitter @RonGreezy.
  • PL Sauce

    Great article, great selection!!

  • Ronald Grant

    Thanks very much for reading and supporting!