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Olatunde Osinaike’s playlist for his poetry collection “Tender Headed”

“Needful as I was for a soundtrack to deploy during the daily affairs of my life, song remained the one street I could play within.”

In the Book Notes series, authors create and discuss a music playlist that relates in some way to their recently published book.

Previous contributors include Jesmyn Ward, Lauren Groff, Bret Easton Ellis, Celeste Ng, T.C. Boyle, Dana Spiotta, Amy Bloom, Aimee Bender, Roxane Gay, and many others.

Selected by Camille Rankine as a winner for the 2022 National Poetry Series, Olatunde Osinaike’s poetry collection Tender Headed is a moving and vulnerable examination of Black masculinity.

The Millions wrote of the book:

“The push-and-pull of form in this debut from Osinaike is such an impressive balance, spanning from reverent prose pieces to something like the interesting construction of Etymology of Simp; with its two columns, verses square and stark, inviting the reader to confuse the line appropriately for the coming-of-age narrative it presents. Selected by Camille Rankine for the National Poetry Series, this collection simmers thoughtfully through considerations of Black masculinity and boyhood, introspective and precise in its critical eye—but always tender, always earnest.”

In his own words, here is Olatunde Osinaike’s Book Notes music playlist for his poetry collection Tender Headed:

Olatunde Osinaike’s playlist for His Poetry Collection “Tender Headed”

If you were to ask, I’d say 8.6 times out of 10 what advances my venture deeper into a song is its instrumental. More times than not, it’s the background that gets to me, moves me. A more wayward endeavor, but beautiful still, is the intention from which I suppose songs measure endings. To suggest a song is fully successful at crossfading and/or moving on is to suggest songs are not honey, that they are not sticky and thus are clean artifacts. To be sure, songs do stop, words hush and albums do finish in an agreed-upon duration but I don’t believe that which blooms from creation can ever be tidy.

Writing Tender Headed over these past few years, I thought a lot about transitions and grew more fascinated by music’s insistence for study of the formative. Needful as I was for a soundtrack to deploy during the daily affairs of my life, song remained the one street I could play within. Throughout the book, each of the poems became their own site or intersection that lobbied for the pause and witness it takes to recognize place, power, and position.

As does the title of the book, the working title of this playlist (“Perdendo”), which these lingering songs belong to, clarifies an ending by its possibility ahead, a castle of opportunity that becomes only in the face of growing conclusion. On the other side of a song’s start, who knows where I’ll end up. Who knows if that even matters? For now, I have the ability to rewind and treasure known delights along the way.

  1. Nico’s Red Truck by Dijon

“I’m afraid I might forget / what if the good memories start to fade out“

At the 1:51 mark, the music video for this song (would encourage you to view, if you have the chance!) shows a Black mother and daughter mounted up on a horse. The daughter yawns; it happens for no longer than a split second in the sepia frame of my computer, but I remember when I first saw it five years ago. How I yawned in response, unwittingly. It is said that yawning is a behavior, like laughter or scratching an itch, that can be attributed to social mirroring. Imitation as an emotional event. I did not know the daughter then nor now. Though in a lot of ways, the book attempts to review that kind of tie between Black folks and the chemistry that results from that behavior. More significant, the language we lean on when confronted by the brief reappearance of emotion. When I hear this song, as I did during the earliest stages of this book, a past rushes back (un)expectedly and I wonder about how well I’ve prepared my language to embrace it. No matter the detail, no matter how hardened I’ve mistaken myself to be to it.

  1. Myself When I Am Real by Charles Mingus

The most beautiful song I’ve ever heard that needed hearing. Its improvisation, its long-windedness (almost 8 minutes long), its excessive turns, its run-ons lacking resolution. I owe the vibe of the book to it partly because its title was a declaration I struggled with. There was a time when the contrarian in me took any self-love declaration to task. And it was through writing this book – the months I spent interrogating my own action, my own understanding of love as that action – that I understood The Angry Man of Jazz a little more fully and what it could mean to remain adamant about each of your moods.

  1. Nah It Ain’t The Same by Greentea Peng

I, too, admire the certainty of this track though my feelings about it have changed since I first let it spin. That is, in part, due to what Greentea Peng has noted about its intention – how its usage of ‘man’ is meant more universally and not as fixed to gender as one might first assume. But it is also because as I took her craft in, I subtracted more and more from whatever one might call the takeaway. Greentea does not propose a solution; she only proposes consideration. I like that and I’d add that, as readers move through this book and its poems, they can see the same sort of leaps.

  1. Long Run by Smino (feat. Via Rosa)

I’ll keep this one brief: no artist influenced the rhythm and musicality of this work more than Smino. His topical range and punny tactics aside, his use of alliteration and enjambment in verse is inspirational and helped me churn through a number of poems in the book.

  1. An Interlude Called “Circus” by Saba (feat. Eryn Allen Kane)

If there were a close second to this argument made above, Saba would be in the mix. Coming from the same neighborhood as me and thinking even of the small sample size of time we shared space together (shoutout LINK!), it is important to note his care and intention in carving out room to memorialize Chicago, its love and spirit. Besides, I have a special place in my heart for any song that can make the ride to its image feel like a quick ride home. Now I like to think I’m not especially biased about which songs can lead me to this place, but most often for me this happens with interludes! And with this song, I’m glad to call the ‘Circus’ my West Side, which has nurtured ya boy and the many poems that came out of that cultivation.

  1. Temptations by Omah Lay

“How do you love like that / your eyes no dey dry water”

This is where I say, if you find the time to come hear me read from the book this upcoming winter and spring, you will undoubtedly hear this song. As it was (probably!) the most repeated song in this playlist during my time writing and developing the book, it’s only right that I share that it’s my baseball walk-up equivalent. I can’t say who all Omah speaks to during this two and a half minute session, but it felt a lot like speaking heart to mind for one’s own self. Hearing another, coming from where I come from, float in an airiness of this song and curate moments of both interrogation and intimacy shifting from “when I don backslide in my passions / and in my prayers” to “my day one / from way back / you dey there / you no give up”. It was nourishing to be sure, hearing him face hitches without eluding or recusing. As I went through my own journeys. I did my best to instigate gentleness in the same way.

  1. Skippin Work Today by Eddie Kendricks

The first track that ever got added to this playlist was this one. It could serve, appropriately so, as an outro for the days I logged off after wrestling with the occupations of my mind, whether at work or with writing. Its feat of relaxation, likened to a retro Black sitcom’s opening theme song, was one of easy listening that connected with me. And if I’m honest, Eddie sang like he needed a hug. I felt that.

  1. News Come by Mereba

“I see the future / I see so clearly / I see the vision / inside the children”

A subgenre I feel to be particularly untended, this Black folk soul song by Mereba touches on many themes shared in the book, like Black liberation and the processing of agitation and discouragement in marginalized communities. It is music of the same curb this book stands on and of the same sky that can pour rain to wash away tears. It is quite a gem and one that ties into the same histories this book looks into.

  1. Gwendolynn’s Apprehension by Mick Jenkins

“be too cool for me / too many social rules for me /

I’m in the party and he think he schoolin me”

Another Chicago artist shining, Mick Jenkins speaks life into the striking words of Gwendolyn Brooks’ poem “We Real Cool” for the hook of this song. Around the time I first encountered it, I was so preoccupied by other tracks on the album (“Pieces of a Man”) that I almost missed out on truly hearing this one. (A fun fact: an almost-epigraph for this book takes place in Heron Flow 2 – “how is it that we’ve come to quantify the whole of a man, only by what he looks like in the light?”) But I’m so glad the hook was what it was. It stopped me just long enough to observe Mick at his best: treasuring the gold of staying in step with yourself and no one else.

  1. Runnin Away by Sly and the Family Stone

In the book, there’s a camp of poems I affectionately call the “lyre” poems. “Lyre” holds two stations here for me: (1) it’s the etymological base word for the word lyric and (2) when said aloud it sounds like ‘liar’. These poems take notable punchlines from hits by Black male rappers and bid to follow up with the lyric’s declaration. Exploding the readied stakes of the lyric into a petition for interrogation, application, and resolution. As a music archivist and longstanding sample lover, I’ll note that each of these artists have sampled the work of this distinguished group. While researching for the book, I found this particular song (though none of the artists sample it) to be striking for another two reasons: (1) the ones they do sample all extend from a distinct era of Sly and the Family Stone’s music unlike this song and (2) the tone of this song coupled with the sharp “hee-hee” ad-libs throughout lend it a different layer to view its escapist fabric from.

  1. Best Life by Cardi B (feat. Chance the Rapper)

Life is not without its candy, and musically that is what this song is to me. A perfect coupling of artists for what is incredibly fun and a must-have on this playlist. Sometimes you have to encourage yourself in the midst of life’s fog and I appreciate Cardi and Chano for taking time out of their schedules to show us a way to do so.

  1. The Bird by Anderson .Paak

“working my fingers to the bone / see, I do the best I can /

mama was a farmer / papa was a goner”

Circling back to this song for the nth time, Anderson’s staggering use of motif here was one that drove me toward writing the following line: “we are still living in a time full of prerogatives, a city of exaggerations headed southbound”. Typically, Anderson brings me to a groove but here he brings me to a standstill. It is an unassuming song that granted me a whole workshop on the tide of choices, the vow of descriptive language and how to reconsider momentum in poem, in song, and in life.

  1. Maybe Tomorrow by Grant Green

I find that when I am writing, self-censorship can sneak its way in. A method I have discovered that combats that balking is music that nudges me toward stalling. The work can be already so urgent, so balance is vital. Songs like this level me into a displacement from whatever space I’m in tangibly, a lounging environment where the impending word would be anything but an interruption. That way, whatever I say has every chance to fit in.

  1. Static by Ari Lennox

Candidly, as a fan, I’ve witnessed Ari feel rejection. In many areas but explicitly for the album this song is featured on, no less, which deserved many more awards than it received. This playlist, which ends the same album as that album does, is a prize unto itself. What Ari does with this track, I fully believe, should be studied and that is admittedly tied to my bias for it. Near the onset of this book, I ordered a banner from Rayo & Honey which has been planted onto the wall above my desk since. It reads ‘Joy Is An Act of Resistance’ which is a deliberation this book wrestles with. I think the heat of the static Ari refers to in this song deals with many things. Every time I hear it, I think of that heat as noise and as necessary background from which the clearing can begin.

The songs below are marked in case you’d like a little more time to linger.

Bonus Tracks:

  • Awards Show (Interlude) by Mase

Another interlude (!) that takes the shape of an acceptance speech and Mase gives us a sincere glimpse into the immeasurable. The closer you get to the gold, the more your tribe should shine. Keep them close.

  • Windows by Donnie Trumpet & The Social Experiment

A tune that is both playful and sobering that served as another mirror into not forcing the word. Words spilled as they had to once I realized it is not the concern of voice to be reliable or incorruptible.

  • Talkbox Medley by Stevie Wonder [Never Can Say Goodbye by Jackson 5 + (They Long to Be) Close to You by Dionne Warwick + Close to You by Frank Ocean]

Once, my thought of the work of writing was consumed by craft, by what I lacked and what I couldn’t do. But what I could, was play. Stumbling upon this 1972 Stevie Wonder performance in the aftermath of Frank Ocean’s 2016 album Blonde, I started to refocus my poems on their one true subject: leisure. 


For book & music links, themed playlists, a wrap-up of Largehearted Boy feature posts, and more, check out Largehearted Boy’s weekly newsletter.


Originally from the West Side of Chicago, Olatunde Osinaike is a Nigerian American poet and software developer. He is the author of Tender Headed, selected by Camille Rankine for the 2022 National Poetry Series. He is the winner of the 2019 Lucille Clifton Poetry Prize, a 2019 Frontier Poetry Industry Prize, and honorable mention for the 2019 Ploughshares Emerging Writer’s Award in Poetry. His work has appeared in Best New Poets, New Poetry from the Midwest, Kweli Journal, Wildness, Southeast Review, and elsewhere. He lives in Atlanta.


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