I hate cutesy messages, but this one never bothered me.
Reddit is a fun site, and can have a fun error message.
Oh I agree, this totally would be on point for Reddit at the time. However, not only did the user-base change, Reddit did as well; Between the ads, awards, and NFTs... errr... avatars, I feel that Reddit is now a lot better off financially than it was back then (I could be totally off-base here) and so the expectation is that it should now no longer be in a situation where my specific visit to the site took down the one MySQL box in the storage closet.
When we added it 16 years ago, people thought it was cute and funny. In fact, people loved it so much we sold t-shirts that said "I broke reddit" with one of the injured Snoos, and they sold out super quickly. This was probably due to the fact that the majority of users were engineers, many of whom also ran user facing sites, so they could empathize.
Maybe these days it makes less sense since the user base is so broad. But I'm not involved anymore and honestly it's sort of part of the brand now.