This isn't super early and not really iconic and I forget why I saved it, but this is a self-professed journalist getting absolutely owned in 2013 or so and then deleting his own thread after posting correspondence with someone who had requested confidentiality.
Also an actual rather iconic one from the days of gifs.
The rather complicated story of why this happened.
It's a video and not an image but it's ancient. Pre-2000 even. If you saw this when it first came out it was likely you were using an actual phone modem.