Pen Game — The Apprenticeship Track

Thesis. “Pen Game” is the song where a seventeen-year-old does his homework on the form. Every move in it — the geographic claim, the body-the-opponent boast, the punchline structure, the shock-value insult — is a battle-rap convention being rehearsed by a kid who knew Skyzoo was about to listen back to it. The single thread to follow is the pen itself: not as metaphor, not as theme, but as instrument being learned. This track is the workshop. Some of what gets practiced here will become part of Mac’s signature for life. Some of it will be discarded inside a year. Some of it never should have been written in the first place. That’s what apprenticeship looks like when you can see the lathe.

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The MySpace track

October 2009. Mac is seventeen, still finishing senior year at Taylor Allderdice, halfway through the most prolific calendar year of his career. The Jukebox: Prelude to Class Clown dropped in June. The High Life will drop in December. In between, somewhere in the messy connective tissue of a teenager building a catalog the old-school way, he does the thing every ambitious kid in 2009 did: he goes on MySpace and DMs someone he respects.

The someone is Skyzoo. Brooklyn underground, real reputation, the kind of rapper rap fans named when they were arguing about bars. The Salvation — Skyzoo’s debut album, the one that put him on every backpack rap blog’s year-end list — came out in September 2009, one month before “Pen Game” was recorded. Skyzoo was right at the peak of his “everyone who cares about lyricism is paying attention to me” moment.

A kid from Pittsburgh slid into his DMs. Skyzoo, years later, would remember it as the moment he realized Mac was most dope indeed — Skyzoo’s words, repeating Mac’s own crew tag back at him.

What I want to sit with is the asymmetry of that. Skyzoo in October 2009 has a critically acclaimed debut. Mac in October 2009 has two mixtapes nobody outside Pittsburgh has heard. The legitimization runs only one direction. And the song is about that — it’s about the pen, about who can write, about lyrical credentials. The kid showed up to a track called “Pen Game” to share a beat with a rapper whose pen game was the entire reason the kid wanted him on it.

That’s the apprenticeship.

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The single thread: pen as instrument

The whole song is about writing. Not about love or money or pain or weed — about writing. The chorus is literally a brag about being able to write a verse anywhere (“In the middle of Alaska I’ll write a heater”). The verses are about being a better penman than the opponent. The hook word in the title is pen. Skyzoo’s standout line is I’m the penner of the penners.

Track this thread and the song becomes legible in a way it isn’t if you read it as just braggadocio. Mac isn’t flexing wealth, women, status, geography in any deep way. He’s flexing craft. Specifically: the craft he’s still in the process of learning.

Listen to how he opens his first verse:

With my man Skyzoo, it’s the class clown of his high school
Drown you in typhoons, hittin’ you with rhyme too

Line one is the brand statement — Mac is already referring to himself as class clown, the title of the previous mixtape, a self-mythology three months old. The seventeen-year-old has decided what character he plays and he’s already wearing it like a stage name. Line two is the pen demonstrating itself: Skyzoo / clown of his high school / drown you in typhoons / hittin’ you with rhyme too. The whole couplet is a vowel-locked rhyme scheme (zoo / school / typhoons / rhyme too) that wants you to notice it noticing itself. He’s showing his work.

Then this:

We stay high like Einstein’s IQ

This is the kind of bar a seventeen-year-old who studies the form writes. It’s a clever-corny pun — high (weed) and high (IQ) and Einstein the cultural shorthand for genius — and it lands somewhere between clever and trying too hard to be clever. Big difference between this and the bars on the same tape’s One of a Kind, where the surface is brag but the underneath is dread. There’s no underneath here. The underneath is did you catch the rhyme scheme?

And that’s fine. That’s appropriate. That’s the form being studied. Battle rap isn’t supposed to have an underneath — battle rap is supposed to demonstrate the pen. The whole point of the apprenticeship is that the surface is the thing.

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The bar that’s actually good

Every once in a while in the apprentice phase, a young writer drops something that you can tell they knew was good when they wrote it. Mac has one of those in the chorus:

In the middle of Alaska I’ll write a heater

Read it twice. Heater in rap means a hot verse — slang has been there since the eighties. But heater in normal English means a heating device. In Alaska you don’t really need a hot verse. In Alaska you do need a heating device. The bar works on both axes simultaneously: even in the coldest place imaginable, even where my pen game would be the least relevant flex, my pen would still generate what’s actually needed. Heat as art, heat as survival, same word, same line.

The repeat in the hook is the giveaway. Mac wrote the bar, knew it was the bar, decided to use it as both the opening and closing line of the chorus so you’d hear it four times before the song ended. He wanted you to notice. He wanted Skyzoo to notice.

This is the kind of bar that survives — the kind of construction Mac is going to do a lot more of as the catalog matures. By So Far to Go from the same Pittsburgh era, he’s writing whole verses where the double meanings stack on top of each other instead of standing alone. By Avian on WMWTSO, the wordplay is so dense the song refuses to declare what it’s actually about. The Alaska bar is the bar where you can see him deciding he wants to be a guy who writes those.

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What Skyzoo brought

Skyzoo’s verse is a different machine than Mac’s. Listen to it as a craft demonstration:

No sleep, no retreat, no surrender
No apologies from me, I’m the penner of the penners
I mean what I speak, so if I’m givin’ you a sentence
Then it be’s what it be’s, nothin’ hid on the agenda

That’s an anaphora cluster (no sleep / no retreat / no surrender / no apologies) into a rhyme-and-syntactic-parallel pattern (sentence / agenda tied to I mean what I speak / it be’s what it be’s). Skyzoo is doing something Mac at seventeen is not yet doing — building rhetorical scaffolds where the grammar of the lines is the architecture, not just the rhyme. It’s the difference between bars that are skilled at the bar level and verses that are constructed at the verse level.

You can feel Mac listening. By the time you get to verse three, Mac’s flow has gotten denser, more rhythmically aggressive, more rhyme-per-line:

I rip mics to pieces, cook ’em or eat ’em raw
Was bustin’ freestyles before I could read at all

That’s an internal rhyme on top of the end rhyme (pieces / mics / rip, then raw / at all) and a self-mythology bar (I was rapping before I was literate) folded into the same couplet. It’s tighter than verse one. Verse one was him introducing himself; verse three is him after Skyzoo’s verse landed and he can’t be loose anymore. The apprentice is taking notes inside the song.

This is the part of “Pen Game” that gets missed if you listen casually. The verses aren’t just sequential — they’re responsive. Mac is writing the second half of the track having heard the first.

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The bars that haven’t aged

I’m not going to skip past it.

Verse three has lines that are ugly. And you gets no love like a man with AIDS / I fill you dancin’ gays with some hand grenades. That’s shock-value battle-rap homophobia. The 2009 underground rap context — especially the kind Skyzoo and Mac were both swimming in — treated those bars as ordinary. The genre treated them as ordinary. That doesn’t make them defensible in 2026. It also doesn’t make them defensible in 2009. They’re bars from a seventeen-year-old white kid trying to sound hard on a track with a respected New York MC, and he reached for the worst tool in the kit because the kit had it sitting on top.

Part of what apprenticeship in any form means is that you do the form imperfectly while you’re still figuring out which parts of it to keep. Mac’s later catalog tells you which parts he kept. The penmanship — kept. The double-meaning constructions — kept. The casual queer-bashing slur — dropped. Hard. By the time you get to the Faces-era catalog, that vocabulary is gone from his pen. It doesn’t come back. The apprentice learned that that particular convention was one he didn’t want.

That’s the long version. The short version: those bars are bad, the kid who wrote them got better, and pretending the bad bars aren’t in the song to protect the catalog is a form of dishonesty that does the catalog no favors.

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The class clown can’t help himself

Even with the form he’s learning being battle-rap-strict, Mac keeps slipping in the goofy:

See, I fucked this track, worried that I got it pregnant

That’s a clown bar in the middle of a battle verse. Skyzoo wouldn’t write that. Skyzoo wouldn’t want to write that — it’s tonally off-brand for the seriousness his verse is operating in. Mac can’t help it. The class-clown-of-his-high-school self-mythology he opened the song with is real. Even when he’s trying to be the lyricist battle rapper, the goofy keeps leaking through.

This is the seam in “Pen Game” that tells you who Mac is going to become. The pure battle-rap MC has no use for the goofy line; it breaks the spell. But Mac will go on to make a whole career out of letting the goofy and the serious sit on top of each other — Best Day Ever is goofy on top of dread, Diablo is dark on top of cartoon, the entire Larry Lovestein side project is a put-on smirk over real songwriting. The artist who can’t help dropping a pregnancy-joke into a battle verse is already, at seventeen, the artist who isn’t going to be a pure anything. He’s going to be a hybrid by temperament, because the goofy isn’t a choice — it’s a tic.

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Where the pen goes from here

If you take the pen-as-apprenticeship thread and follow it forward, you can mark the stations.

The Jukebox / The High Life era (2009): pen as proof of credentials. Look what I can do with words. The form is the message.

K.I.D.S. (2010): pen as voice-finding. He stops trying to prove the pen and starts trying to use it. Knock Knock, Senior Skip Day, Traffic in the Sky — the pen is now in service of a feeling, not the other way around.

Macadelic (2012): pen as confessional instrument. Clarity, Lucky Ass Bitch, Fight the Feeling. The pen is starting to be used to open him instead of defend him.

Faces (2014): pen as exhibit. The pen documents what’s happening to him in real time. Some of it he can’t even spell out — he just puts it on the tape.

Swimming (2018): the pen has gone interior. He’s barely “rapping” in the old sense anymore. The pen has become a melody-and-thought instrument. It’s the same pen. The thirteen-year-old in 2005 learning bars in Pittsburgh, the seventeen-year-old in 2009 trading verses with Skyzoo, and the twenty-six-year-old in 2018 writing Self Care are using the same instrument. They’re just at different places in their relationship to it.

“Pen Game” is the kid practicing scales. It sounds like practicing scales. That’s not an insult — every great musician practiced scales. The reason scales matter is that one day they go away and you can’t hear them anymore, but the muscles are still there.

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The thing the casual listener probably misses

The song is not, despite the title and chorus, about being the best writer. Listen carefully: Mac never says he’s better than Skyzoo. He says he’s better than abstract MCs. He says his worst verse is hotter than your best rhyme — but your in the chorus is the imagined opponent, not the guy in the booth next to him.

This is etiquette. Mac at seventeen knows where he is in the hierarchy. He’s on the track with Skyzoo because Skyzoo let him be on the track with Skyzoo. He’s not going to use the track to claim he outdid Skyzoo. The flex is sideways — at the absent third party, the MCs who aren’t on the song. The actual co-star gets respect by way of the implicit we’re on this song together against the rest of them.

That’s a small thing and it’s a generous thing. It’s also a politically smart thing for a young rapper to do when an older one extends him a guest verse. Mac knew the etiquette before he had the leverage to break it.

Open QuestionWhen does the pen become something Mac can trust to do work he himself hasn’t planned? On “Pen Game” the pen is doing what he tells it to. He’s writing braggadocio so he writes braggadocio bars; he’s writing about being a lyricist so he writes about being a lyricist. There’s a 1:1 between intent and output. By the time you get to something like Stay on The Divine Feminine, or the looser parts of Swimming, the pen seems to discover things mid-verse — to put down a line whose meaning the writer himself doesn’t fully know yet. The pen has become a sensor, not just an instrument. When did the changeover happen? Not on “Pen Game.” Not yet on The High Life. Maybe somewhere in the Macadelic sessions, when sustained interiority becomes part of the toolkit. Maybe later. But the changeover is a real thing in the catalog and “Pen Game” is on the early side of it — the pen here is still a hammer, not a stethoscope.

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Key takeaways

• “Pen Game” is the apprenticeship track. Every move in it is a battle-rap convention being practiced by a seventeen-year-old who knew Skyzoo would be listening back.
• The heater in Alaska bar is the moment you can see Mac decide he wants to be a guy who writes double-meaning constructions. He gets a hundred more reps of it across the catalog.
• Verse three is responsive — denser and more rhyme-per-line than verse one, because Skyzoo’s verse landed between them. The apprentice is taking notes inside the song.
• The track contains shock-value homophobic bars that haven’t aged. Mac’s later catalog drops that vocabulary entirely. Apprenticeship includes learning which conventions to keep and which to discard.
• The goofy keeps leaking in even inside the strict battle-rap form (I fucked this track, worried that I got it pregnant). That tic is the seed of the hybrid artist Mac will spend the next nine years being.
• The flex in “Pen Game” is sideways, not against Skyzoo. Mac at seventeen had the etiquette of the form before he had the leverage to break it.