Checkpoints

Insomnia as a kind of border

Some songs describe a place. "Checkpoints" describes a state of mind that behaves like one: the half-lit, over-alert condition of a person who cannot stop standing guard. It runs barely over three minutes^[1], it is the third track on Hiding Places, and it spends that time building a portrait of unrest that feels both personal and political.

The music does much of the work. One reviewer calls the production fuzzy psych rock^[5], and another hears woozy, reverb-soaked kicks and minor-key fuzz^[4]. The beat does not groove so much as list, as if the floor were slightly tilted. Over it, billy woods pushes toward one of the album's many operatic crescendos^[4].

Where it sits

Hiding Places arrived on March 29, 2019 through Backwoodz Studioz, a collaboration between the Brooklyn rapper billy woods and the Los Angeles producer Kenny Segal^[1]. The two had been circling each other for a while. Segal produced Milo's 2015 album So the Flies Don't Come, which featured Elucid, woods's partner in Armand Hammer, and then made beats for that duo's Rome and Paraffin before the pair decided to make a record of their own^[1]. The Passion of the Weiss review describes the project as growing organically out of the sessions that produced Paraffin^[4].

"Checkpoints" belongs to what The Fader's Paul Thompson calls the album's opening four-song suite, one with snarling, serrated guitars that sets an aggressive and foreboding tone^[2]. That is the right company for it. By the time the track arrives, the listener has already been told that this will not be a record of relief. Another reviewer points out that it contrasts with the claustrophobic melancholy of the track that follows, "Spider Hole"^[5], which gives the early run a push and pull between fuzz and dread.

A sleepless palace

The central image, in the account of one critic who singles the track out, is a figure who has fallen from a position of power and now cannot rest^[4]. The scene is of pacing through the rooms of a grand house at night, of flinching when the phone rings, of expensive bedding that offers no sleep. I am describing it in my own words, but the picture is consistent: comfort that has curdled into surveillance.

It is a striking inversion. Palaces are supposed to be the opposite of a checkpoint. They are where you are protected from being stopped, searched or questioned. Here the protection fails. The deposed ruler is still inside the walls but has lost the sense that the walls belong to them.

Checkpoints as a way of living

The title is plural, and that matters. A checkpoint is a single physical place, a roadblock or a border post, but the plural suggests a life organized around them. Each one is a moment when a stranger with authority gets to decide whether you pass, what you are carrying, and what your papers are worth.

woods has long been a writer attentive to the afterlives of empire and the way violence travels across borders. Passion of the Weiss describes him as the son of a Zimbabwean revolutionary and a college professor^[4], and reviews of the album repeatedly note its African-war references alongside its American ones^[5]. That double vision is what makes a word like "checkpoints" so elastic in his hands. It can evoke a military roadblock abroad, a police stop at home, a bank's verification, an insurer's form. Stereogum's Tom Breihan reads the album as a study of being broke and Black in America, citing songs about a bank balance, a previous tenant's mail and an insurance letter^[3]. Each of those is a checkpoint of a different kind.

Hiding as a response

The album's title gives the clearest key. Thompson reads the record as preoccupied with hidden behaviors coming to light, with things left unsaid even to loved ones, and with the urge to sever ties^[2]. He also notes that woods himself famously avoids showing his face in press photos or videos^[2]. Hiding, in this reading, is not only a theme but a practice.

Seen that way, the sleepless figure in "Checkpoints" is not simply a casualty. They are someone who has learned to treat every ring of a phone as a possible summons. The song captures what it feels like when vigilance becomes permanent, when you rehearse the next interrogation in the dark because the last one never fully ended.

The sound of being stopped

Segal's production is often described in terms of friction. Breihan calls the album's sound a heavy skronk-lurch of detuned guitars, drowning synths and drums that thud where most would thump, and says it recalls Pere Ubu more than DJ Premier^[3]. Another reviewer notes that his Los Angeles beats are far more spacious than the New York productions woods had typically worked over, giving the rapper emotional and technical room^[5].

"Checkpoints" uses that room to stage a tension between the loose and the tight. The instrumental smears and wobbles, while the writing is, as Passion of the Weiss puts it, tightly coiled, a place that is both a refuge and a prison^[4]. The collision is the point. A listener never gets to relax into the groove, just as the song's subject never gets to relax into the bed.

A writer with a lot of miles on the clock

It helps to remember how much work stands behind the record. Thompson notes that by 2019 woods had released five solo albums in seven years, plus four records with Elucid as Armand Hammer^[2]. That productivity shows in the density of the writing, and it also explains why the collaboration with Segal feels less like a debut than a refinement.

The same sense of craft runs through the album's making. woods has said that "Spongebob" was the first song on which he and Segal fully understood each other's vision, and that the song was originally titled "Monotheism" before a chorus about being underwater, an allusion to negative equity, changed its name^[1]. That anecdote is useful for hearing "Checkpoints" too. woods treats ordinary pressures such as debt, bills and paperwork as seriously as he treats war and exile, and he lets one vocabulary bleed into the other.

Why the plainness matters

Reviewers have also noticed that the album is, paradoxically, among woods's most direct writing, even as its scenes resist tidy narrative. "Checkpoints" shows how that works. There is no elaborate plot to follow. There is a room, a night, a ringing phone, and a person who cannot settle. The simplicity is what lets the dread land, and it is why the track is easy to remember even when the details of its wordplay slip away.

Other ways to hear it

Because woods writes in compressed scenes that do not always settle into a clear storyline, as another critic observes of the album generally, listeners have to dig in. There are at least three reasonable readings.

The first is political. The fallen sovereign stands for a regime or class that has lost its footing, with the song as a small allegory about how power produces its own paranoia. The second is personal and domestic, a portrait of anxiety in a modern home where money worries, bad news and unanswered calls make a bedroom feel like a holding cell. The third is a self-portrait, an artist who guards his image so carefully that the guarding itself becomes the subject.

These are not mutually exclusive. Part of what makes the track durable is that its central image can carry all three without strain.

Why it lingers

Critical response to the album was strong. Pitchfork gave it a 7.7, and Breihan called it a stressed-out rap classic^[1][3]. It placed on year-end lists at NPR and Stereogum (both ninth), Vice (eighth) and Time (fifth)^[1]. Thompson called it woods's leanest and best^[1].

The song has also stayed in the live repertoire. A 2025 review of a Boston show noted that woods performed "Checkpoints" and that the crowd was fully engaged with it^[6]. For a three-minute track from a record that is now several years old, that kind of recognition says something about how deeply the song's mood has lodged in listeners.

Closing

"Checkpoints" asks what happens to a person after the authority that scared them has passed, or after they have become the person who fears the knock. Its answer is not a plot but a feeling: a long night in a large room, a body that will not power down. Segal's fuzz gives that feeling a texture, and woods gives it a face without ever showing his own. It is a small song about a large kind of fear, and it makes the case that the most thorough border is the one you carry inside.