The Story of My Slightly Funny Coolio Joke

Coolio, the rapper who absolutely slayed the 90s, sadly died today at the age of 59.

Coolio, the West Coast rapper whose gritty music and anthemic hits like “Gangsta’s Paradise” helped define hip-hop in the 1990s, died on Wednesday in Los Angeles. He was 59.

His longtime manager, Jarez Posey, confirmed his death.

I didn’t know Coolio, but I’ve seen and shared his pictures so many times that I kinda feel like I did. You see, Coolio was the source of one of my longest, lamest, and yet most cherished jokes. Let me explain.

A long time ago, my wife and I would be having one of those married people text conversations and rather than saying “Cool.” like normal husband would reply, I started saying “Coolio.” followed by, after waiting just long enough, a picture of Coolio. I did it once because it was dumb, a weird reference, and just barely funny. Naturally, since it was just a little bit funny, I decided to start doing it over and over again in order to make it more funny. Don’t question my logic. It’s a solid plan. I can assure you that it worked.

Around that same time we got Slack at work and I found the admin section where you can setup automatic replies. Guess what I did? Yes! The dumb little joke had now infected work. No one ever noticed as, shockingly, I was the only person who ever replied to anything with “Coolio” but that auto-reply has been hiding there for over eight years now.

Shortly after I added the Coolio joke to our corporate Slack, and I was having way too much fun with it, a developer in our office said “Now you just need to figure out how to have Coolio appear when you’re talking.” Well that sounded funny too, so I went to work on that and created Conversations Plus which was a web application that opened your microphone and listened until you said a key word and then it showed a picture on the screen. You could have configured it with a long list of keywords, but to start it only had one:

    return {
      data: {
        listening: true,
        background: false,
        chatter: [],
        recoginzer: recoginzer,
        matchers: [
          {re: "coolio", fn: this.handleCoolio}
        ]
      }
    };

We had this running on a screen in the office off and on until we closed that office down in 2016. Every time anyone said the word “Coolio” up popped a random picture of Coolio with his skinny dreads. I can’t tell you how many wonderful and weird pictures of Coolio there are. It’s a lot.

Seeing the terrible news about Coolio, made me think about this dumb joke that is older than two of my kids. At this point I don’t know if I actually still like the joke or if I just like keeping it going. It never really had anything to do with Coolio, but it also had everything to do with Coolio. Would Coolio have like it? I’d like to think so.. Should I stop doing it now? Should I turn off the Slack setting, delete my GitHub repo, and go cold turkey in iMessages with my wife?

I decided already.

The answer is: No.

It’s a tribute now.

In fact, as a fun bonus, it turns out that Conversation Plus still works! Enjoy and feel free to set it up in your place of business!

RIP Coolio. Long live the Coolio joke.