There’s a small, select group of rappers who first got famous for being namechecked on other rappers’ songs; think 50 Cent saying that he’s going to tell us what Banks told him. Even on that small list, though, Fredo Santana stands out. The first that most of us heard of Fredo was also the first we heard of Chicago drill music: Chief Keef’s volcanic fight-starter “I Don’t Like.” The Fredo namecheck on that song didn’t even come from Keef, Fredo’s five-years-younger cousin. It came from guest Lil Reese: “Fredo in the cut, that’s a scary sight.” The Fredo who appeared in the “I Don’t Like” video wasn’t even really a scary sight; he was just one more fired-up shirtless kid in a living room full of them. But Fredo steered into that characterization anyway, honing a persona as a face-tatted wraith, a dangerous person even within a scene of dangerous people. His glare, his deadpan singsong, his propensity for posing like horror-movie villains on his mixtape covers — it all played into that image. But Fredo’s death this past weekend, at the tragically young age of 27, throws that image-crafting into stark relief. Fredo wasn’t a monster. He was a traumatized young man, one of many.
Listening back to Fredo’s music over the past few weeks, a pattern emerges. Fredo was a limited rapper, but he was also a malleable one, and that’s what made him such a great collaborator. Fredo was never concerned with having the best verse on whatever song he was on; he seemed to care much more about giving the song a creeping-dread vibe, anchoring it in the ominous. Maybe that’s why Fredo, more than pretty much any other drill rapper, worked with rappers from outside the drill scene. Kendrick Lamar put in one of his all-time great verses on one of Fredo’s songs, 2013’s “Jealous.” And Kendrick’s performance — his flaunting of his Chicago roots, his profession of love for Harold’s Chicken, his dive into mental darkness — makes sense because it’s a Fredo Santana track, because of the context of darkness and wildness that Fredo brings to it. The same is true of Childish Gambino flexing about his Tesla on “Riot.” And maybe it’s why Fredo turned up on tracks with Future, Gucci Mane, Kodak Black, and Kevin Gates — or, more accurately, why they showed up on tracks with him.
Fredo came from drill music, and even as he worked with all these people from different cities, drill music was always his base. He wasn’t interested in transcending drill; he only wanted to perfect it. He didn’t have the star charisma of his younger cousin, but he did have a hissing intensity, a sense of ecstatic instability. He rode with that. Again and again, Fredo rapped about shooting and robbing and kidnapping. And maybe, in the sheer purity of his vision, Fredo was influential. (My first thought upon seeing 21 Savage was that this kid really wanted to be Fredo.) That image was probably what got Fredo his biggest-ever mainstream look, playing a grinning kidnapper in Drake’s “Hold On, We’re Going Home” video. But persona is always a simplification, and that’s more true of Fredo than it is of most of his peers.
Fredo didn’t project pathos. That wasn’t his lane. On his songs, he put forth the hardest image possible. But on social media, Fredo felt a bit more free to describe the forces behind that image. Fredo had, after all, grown up in Chicago, watching friends getting gunned down ever since childhood, and he suffered the aftereffects of all that death. Last September, responding to a photo of the rapper Russ in a T-shirt that made fun of rappers using Xanax and lean, Fredo tweeted, “Until I can stop thinking bout my dead homies an the trauma that I been thru in my life that’s when I’ll stop.” A month later, Fredo was in the hospital, suffering from liver and kidney failure. He started tweeting about wanting to get his life together: “I got ptsd… I was running from my old life tryna get high didn’t want to face them demons.” He never got the chance.
On Friday night, Fredo died after suffering from a seizure. It’s not immediately apparent whether his death had anything to do with lean, but codeine can trigger seizures. If Fredo was a lean casualty, he wasn’t the first, and he probably won’t be the last. But his passing does force us to rethink the way we think about drugs and rap stardom and the sort of hardness that rappers like Fredo have long projected. Those things are all dangerous. But for a lot of people, they’re a way of coping. There’s been a lot of ink spilled in recent years about the way the opioid epidemic has affected rural America. But its effect on kids like Fredo, black kids from rough parts of American cities, is just as harrowing. Fredo built a whole career on that “scary sight” line. But the conditions that he came from were a whole hell of a lot scarier.
1. Payroll Giovanni & Cardo – “Stack It, Stash It” (Feat. Jade Jones)
Before Fredo passed, I was planning on writing this week’s column about Payroll and Cardo’s excellent new album Big Bossin’, Vol. 2, which comes out Friday. Now, with Culture II coming out on Friday, I don’t know if I’ll have a chance to write about Big Bossin’, Vol. 2. So just know that there is a very good album full of smooth and efficient street-rap awaiting you in a couple of days.
2. Dreezy – “2nd To None” (Feat. 2 Chainz)
2 Chainz’ second-best punchline on this: “I don’t even think weed strong unless that I cough / And my mama house so big she went downstairs and got lost.” But his best punchline is a gloriously dumb single-entendre — “I’m second to none, I’m next to a nun, she naked / No disrespect to her, my check long, it’s a confession” — and it’s on the actual hook. But this isn’t 2 Chainz’ song. Instead, it belongs to the persistently underrated Chicagoan Dreezy, who makes trap bangers sound so effortless that she ends up being overlooked for being too breezy.
3. Black Milk – “Laugh Now, Cry Later”
The burbling bass, the hiccuping drums, and the smeary, gasping sample are enough to throw you into a whole new mental universe, and they’re enough to make Black Milk’s damn, the world is fucked up lamentations (“Lames, giving they opinion on her persona / Ma, wear your hair, makeup the way you wanna”) sound truly deep. And you know what? Maybe they just are deep.
4. Nipsey Hussle – “Last Time I That Checc’ed” (Feat. YG)
Maybe one day I’ll be tired of hearing craggily smooth fuck-you-up Los Angeles rap songs, but I can’t imagine when or why that day would arrive.
5. SOB x RBE – “Once Upon A Time”
If you ever want to get my attention, just build a Bay Area rap banger around a sample of Bananarama’s “Cruel Summer.” It’ll always work.
IT WAS ALL GOOD JUST A WEEK AGO
Russ deleted this tweet and realized he can't show his inner Aryan feeling until he transitions away from hip hop and becomes the Diet Pepsi version of Kid Rock 😭😭😭😭 pic.twitter.com/i7N0TjGpm6
— Ahmed/Drakeo & 03 Greedo are the greatest (@big_business_) January 21, 2018