Here's a deep dive. Back in the day, I was a frequent visitor of the Homestar Runner website. One of the things I discovered there was a web blog called, "Strong Sad's Lament."
hrwiki.org/wiki/Strong_Sad's_L
Anyways, one of the songs I saw was called "Transformer Man" by Neil Young. It's quite an oddity because all the lyrics are sung using a vocoder. It gives the song a very robotic feel. It's unlike any song I've ever heard from him.
youtu.be/iHdS1zdhWQs

@Magnetron1
I used to laugh my a$$ off watching StrongBad's Emails.

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@1000dannyboy For sure. My favourite ones are the Japanese cartoon and the dragon emails.

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