#118, “5 Out of 6,” Dessa (2018)

150 Favorite Songs: #118, “5 Out of 6,” Dessa (2018)

I love boasts in hip hop, the way that a brash declaration becomes a challenge to the listener. Go ahead and doubt me, the best ones suggest. Pusha T taunts his enemies about how they can call “1-800-CALL-MY-BLUFF” if you think he’s just acting like that on a record. Xzibit once declared “my whole skeleton is dipped in titanium,” which can’t be true (you’d die!), but there’s a sort of emotional truth to it anyway. Lil Wayne once rapped in a love song “what you mean to me is what I mean to rap,” which is kind of sweet, in a fucked up, self-aggrandizing way. DJ Khaled, of course, famously declared that all he does is win, win, win, no matter what, and every time he steps up in the building, everybody’s hands go up (and they stay there), which sounds like it must be exhausting, if you’re in a building and Khaled comes in, then realizes he left something in his car and goes back out to get it, then maybe steps back out to take a call. But that’s the point—he’s so good, those hands go up (and they stay there) every time anyway.

Dessa’s boasts on “5 Out of 6” are, I think, my favorite, because she does a thing that none of those dudes have the confidence to do: She qualifies her greatness in a way that makes them more trustworthy, not less.

Dessa is an interesting artist. At the start of her career, she was mostly a rapper who could sing well, and would occasionally do that on her songs—but mostly, she was interested in narrative storytelling in her songs, rapping about things you’d rarely hear in hip hop. Her debut album opens with a song about her love for her younger brother; it goes on to offer a song of support to a rapper’s wife whose husband is kind of a shit-ass, says “I see you” to her; I guess the most famous song on it is the one with the most boasts, a song called “Bullpen” that her fellow Minnesotan Amy Klobuchar played at rallies when she ran for president in 2020, about being unafraid to be the only woman in the room and calling out the boys for their bad behavior. (“In a room of thugs and rap veterans / why am I the only one who’s acting like a gentleman?”) As she evolved as an artist, though, the confidence she displayed on that song led her to vary up what she did musically; her latest album is upbeat, poppy, only sometimes a rap record at all. It’s been a fun progression to observe.

I think everything she does well, though, she does best on “5 Out of 6.” It’s a classic boast song, from the very first line (“double-jointed triple threat” is how she describes herself at the onset, before declaring that she’s “got no time for my detractors / standing on my staircase, all you are’s a fire hazard”). But the key to a great rap boast isn’t just saying something bold and declaratory about your own greatness, it’s delivering it in a way that demonstrates that greatness, which she really does in the second verse, with a nimble set of lines with complicated but immediately satisfying meter and internal rhymes and assonance, a metaphor she stretches to its breaking point without actually letting crack:

and i run a tight ship

every deckhand here has a five-year plan

and an ice pick

they can write code, they can drive stick

i got an octave on you and a high kick

I love that shit—and then she shows up Khaled, acknowledging, “I don’t win ‘em all, but I’d say I take five out of six.” And that, to me, is the magic of Dessa’s approach to music. We know that DJ Khaled doesn’t win all the time. We know Xzibit’s skeleton isn’t dipped in titanium (he’d die!). We know that Pusha T isn’t out there literally murdering his foes. We know that rap would survive just fine, albeit a little less delightfully weird, if Lil Wayne hung up his mic tomorrow. But Dessa’s line here lands in just the right way. An .833 win rate is incredible, means you’re in the playoffs every year and probably bringing home the title most of the time—and it’s plausible in a way that makes the rest of the lines resonate a little harder, too. Maybe she does win that often?

There’s a power in vulnerability that we rarely talk about, and Dessa grasps that intuitively in “5 Out of 6,” which is still one in the long tradition of rap songs about how great the rapper performing it is. It runs through the whole song—“cut my own gills with a pocket knife” is a hell of a way to say “I invented myself to be able to survive anywhere, using whatever tools I had available,” which is a boast but also one that acknowledges that there are environments that you aren’t built to survive in, and that adaptation might leave scars. “I brought a chisel tip to this pencil fight” lowers the stakes of Jay Z’s refrain in “Takeover” about bringing knives to fistfights and guns to knife fights in a way that’s true to who Dessa is—someone whose battles (like Jay’s and Push’s and most other rappers) are fought metaphorically, without the need to self-aggrandize.

There have been lots of times in my life where I want to listen to a song by a rapper who is talking about how great they are, in order to get fired up for whatever. It’s kind of a cliche (here’s Kendall Roy listening to “Takeover” in a town car in Succession), but the fact that rap music can be a first-person power fantasy is part of why the world loves it. These days, if I want that feeling, I find myself reaching for “5 Out of 6” more than “All I Do Is Win,” though. It’s got all the same bravado, but I’ve lived long enough to know that taking five out of six is plenty.