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Halloween is a time of hair-raising chills and jump scares, of cold horrors and creeping dread. Hip hop’s been obsessed with similar scares for decades, with rappers’ ability to incite violence meant to instill fear in the public and naysayers. The gun serves as an instrument of terror, a weapon in more meanings than one. But instead of celebrating the inherit creepiness brought on by the always looming possibility of death, rap instead shied away from actual terror and utilizes it to attract swathes of women and the cool factor the genre mixes with it. Not too many artists actually use the terror they build up. Fredo Santana, however, became synonymous with terror itself; partly because of a conscious effort to be scary, but also just because of himself, period.
Like Lil B, Fredo Santana was a meme of the early 2010s, but instead of his name being attached to the breezier side of rap, it was packaged with a darker meaning. Chief Keef put on for Chicago rap in 2012 with “I Don’t Like,” and through a throwaway line of “Fredo in the cut, that’s a scary sight” from featured artist Lil Reese, the world was introduced to Keef’s cousin five years his senior. Fredo embodied scary; thin eyebrows and a protruding brow made even his blankest of stares appear angry, deadly even. He quickly became hip-hop’s boogieman before even releasing a track. On Halloween, there isn’t a rapper dead or alive that has been able to bring the chills like Fredo Santana did.
Born Derrick Coleman, Fredo was someone that immediately caught your attention when he entered into a frame. Early coverage of him with his imposing image painted him as a villainous character, a product of Chicago’s gun violence narrative that reporters salivated at. He enjoyed the role and played a tongue-in-cheek version of himself in Drake’s video for “Hold On, We’re Going Home.” When he came around to releasing music, he knew exactly what he needed to be, in contrast to many artists who have to find themselves over the courses of their career. On the cover of 2012’s It’s A Scary Sight, Fredo lurks in the shadows looking like he’ll lash at you quick with vampire fangs. It’s simple but unsettling, an early indicator that his brand of gangster doesn’t just extend to gunplay, but a malevolent essence as well.
His second project Fredo Krueger leaned full into his creeper status. The cover depicted him as Freddy Krueger, the infamous slasher of dreaming kids that’s about as scary as one could imagine. His music may have lacked the polish that made the best drill stick like glue to the public’s collective subconscious, but his aesthetic alone was endlessly captivating. It worked wonders for branding purposes. When he threatened to kill Migos the following year, a chill went down the spines of everyone on the internet. People were afraid for Migos. A bubbling rapper whom not too many people knew anything about raised red flags for the Migos safety. When the feud quietly bubbled down without any further mention of beef, Fredo’s eminence grew like the end of horror movies before sequels; he emerged unscathed from a thematic bloodbath on the way to the next victim.
Ironically, as Fredo became more of an approachable person, his aesthetic became increasingly terrifying. Trappin Ain’t Dead could have been the cover of a mid-90s urban slasher film. It’s A Scary Site 2 painted him as a predator on the prowl encouraged by the light of a full moon. He also released Walking Legend which showed him as a baby on the cover, an attempt at humanizing a lethal force. By the time of his death in 2018, he was one of the most charismatic figures in rap, equally feared and respected.
The lingering sentiment applied to Fredo, aside from universal adoration, is the fact that of all of the rappers that exist in mainstream rap, even those who try their best to appear scary, no one’s quite managed to operate like Fredo did. Without weapons, most rappers are harmless—afraid to fight or argue without it. Fredo appeared off-hinged, ready for a scuffle, shootout, you name it. When he told the Migos that he “didn’t give a fuck” about going to jail for murdering them, the world felt that. Perhaps that’s why no one else ever tried him. Just the image of him standing in an alleyway with glowing eyes boring holes in your skull from 10 feet out is enough to make someone sleep with the lights on. Drake noticed it early on and helped him to embrace the role that he was created for.
Horrorcore is a subgenre of rap that can be traced back to the Geto Boys who created horror-themed lyrical content and brought it to the mainstream. DJ Jazzy Jeff and the Fresh Prince had released “A Nightmare on My Street” in 1988 that described encountering Freddy Krueger, but the Geto Boys’ “Assassins” on their debut Making Trouble is largely credited as the song that started it all. It’s become intermingled with rap at large over the years, watered down, with the idea of horror coming from shock plays of murder and sexual violence. Fredo didn’t rap about any of this stuff but managed to transcend the reach of the genre by sheer image alone. When we think of horror in rap, Fredo will always remain the slasher that changed how we think of fear in contemporary hip-hop. Many imitators have come and gone, but there will never be another Fredo.
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