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I Asked AI to Help Me Write an IT Musical. Things Escalated.

It started with a dial-up modem singing a love song. A few hours later I had a two-act musical about incident response, expired certificates, and turning it off and on again.

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August 22, 2026 • 5 min read • 873 words

It started with a dial-up modem.

More specifically, I had the idea that an IT musical should open with a love ballad sung by a dial-up modem trying to connect to another modem.

That seemed like a perfectly reasonable place to stop.

It was not.

A few hours later I had two acts, fourteen songs, an overnight security incident, an expired certificate, technical debt, a questionable backup strategy, and an IT department singing about incident response.

So naturally, I turned it into an album.

IT the Musical album cover

You can also open the full player at music.gregvedders.com/it-the-musical.

It started with a modem

The first song is Handshake of the Heart. A beige PC, a CRT glow, a telephone cord trailing into the wings, and a MODEM stepping into a spotlight like a digital Romeo who has been waiting all night on copper wire.

The joke lands because it is completely sincere:

So pick up the line
And tell me you’re there
Send me a signal
Through the cold midnight air

That set the rule for everything that followed. Treat the most mundane IT concepts with total Broadway commitment and see how far the bit can go.

Then the help desk showed up

Once you have a modem falling in love, the next stop is obviously the help desk.

Have You Tried Turning It Off and On Again? turns the oldest troubleshooting ritual into a full company number. Users arrive in waves. Printers chirp. Someone clicked yes to everything. Someone’s toolbar is purple. Someone’s coffee is cold and the help desk still says reboot it.

From there the everyday IT canon basically wrote itself:

  • It Works on My Machine
  • The Network Is Down

I will not paste every lyric here. That is what the libretto is for. The playlist above is the better way to hear how the comedy stacks up before the story gets dark.

And somehow it developed a plot

Around Someone Got In, it stopped being a collection of IT jokes and became an actual story.

The progression is familiar to anyone who has lived through a real incident:

Someone Got In → Wake Up the Incident Team → It Looked Like Microsoft → Containment

The phishing song is one of my favorites conceptually, because the attacker does not need a clever exploit. They only need a familiar logo and a tired human being with seconds to decide.

Then Act I tries to close the door. Sessions revoked. Passwords changed. Endpoints isolated. The company sings Contained! like the curtain is about to fall on a clean win.

It is not.

By morning, the office is cheerful again in Good Morning, Everything Is Fine while the incident team is still counting copies of a seven-year-old certificate that nobody owns. The password did not matter. The account did not matter. Something they trusted was still trusted.

Act II: the joke gets surprisingly serious

Act II is less about the breach and more about what survives after the alarms stop.

Trust Me is where the musical finds its villain, and it is not a hacker in a dark room. It is a forgotten certificate personified as Trust: elegant, charming, and already approved.

The beautiful thing about trust is
You already said I’m fine

That line does more work than I expected when I started this as a modem joke.

From there the story runs through the cleanup everyone pretends will be quick:

  • Who Owns This? / Temporary
  • Burn It Down and Build It Back
  • Known Good
  • Handshake of the Heart (Finale)

Preparedness, communication, ownership, and the people behind the systems. It turns out a silly musical can land in the same neighborhood as the security posts I usually write, just with more choreography.

The complete album

IT: The Musical: Original Cast Recording

Act I

  1. Handshake of the Heart
  2. Have You Tried Turning It Off and On Again?
  3. It Works on My Machine
  4. The Network Is Down
  5. Someone Got In
  6. Wake Up the Incident Team
  7. It Looked Like Microsoft
  8. Containment

Act II

  1. Good Morning, Everything Is Fine
  2. Trust Me
  3. Who Owns This? / Temporary
  4. Burn It Down and Build It Back
  5. Known Good
  6. Handshake of the Heart (Finale)

The player at the top of this post has the whole album. If you want the dedicated page, it is at music.gregvedders.com/it-the-musical.

Read the complete libretto

The full two-act musical includes all fourteen songs along with stage directions and scene transitions.

Download the lyric book (PDF)

How far one dumb idea can go

None of this existed when I started except for one thought: a dial-up modem singing a love song.

I worked through the story and lyrics with ChatGPT, song by song. Each number suggested where the story should go next. Once the lyrics were finished, I used AI music generation to turn all fourteen songs into actual performances, then built a little self-hosted album player so the whole thing could live at music.gregvedders.com.

Is it going to Broadway? Probably not.

Did I somehow spend my day producing a full-length musical about incident response, certificates, technical debt, backups, MFA, and rebooting computers?

Yes.

And I am surprisingly okay with that.


IT, how can I help you?

“Hi. My printer isn’t working.”

“Have you tried turning it off and on again?”

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Greg Vedders writes about information security, troubleshooting, photography, and the occasional unexpected fix.

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