This story doesn't have the community involvement or thoroughly thought out design elements of some of the other flags, but this is how it really happened.
On March 18, 1998 Frank Harrell (Cowboy Frank) (that's me folks) published his first personal web page. Having been building web pages as a volunteer at the National Park Service for a couple of years, he was not new to web work.
At first Frank placed a copy of the gay rainbow flag on his site. However, his page was about Gay Cowboys, and he thought he should have a flag more representative of the western life style.
Frank developed a flag with a wood grained background, scanned a small rainbow colored cowboy boot from a bumper sticker, and placed it in the upper left corner.
On March 24th, 1998, Frank applied to the Gay Cowboy WebRing which had been founded on December 31, 1996. Robert Williams (Bob), who was the RingMaster at that time, accepted Frank's site on March 26th and sent him the following e-mail.
Welcum -- and hope things stay as good with you as they have been!!
Somehow the e-mail got dropped into the wrong folder and Frank didn't notice it until April 26th. When he found it, Frank panicked! Creating web pages for the Park Service, Frank knew the possible repercussions of copyright infringement, and his flag contained an obviously copyrighted cowboy boot logo.
Quickly, in only a couple of hours, Frank redesigned his flag using the gay rainbow flag as a background and added a cowboy hat from an image in the public domain. The flag was sent to Bob and forgotten.
Over the next couple of months the flag began to show up in a few places on the web, and Frank called his partner to the computer and beamed with pride.
In 2000, Yahoo! took over the WebRing system. On September 1, 2000, Yahoo! turned on their new management system and Bob became frustrated with the new tools, many of which didn't work correctly as the new system was being broken in. Bob asked Frank if he wanted to take over the ring, and by the end of September, the Gay Cowboy WebRing was under Frank's Ring Mastership.
Frank immediatly began redesigning the flag with a cleaner cowboy hat image, which he took using one of his own hats. The new image, which was sharper and crisper, was used as the new Gay Cowboy WebRing logos.
However; the original Cowboy Hat Flag seemed to have just the right touch and has become commonly used around the Gay Cowboy Internet community.
UPDATE: May 3, 2012. After 14 years, I have left the Webring system, invited all the other members to take over my rings and deleted my Webring account. The rings had a good purpose when they were new. They offered a way to easily link similar subject websites of individual folks together. In the last few years, Webring has turned into a purely commercial venture. It has come to my attention that the coding used can, under certain conditions, hijack a visitor coming to one of the pages with Webring code on it and send the user to the Webring home page. Also I have begun to see pornographic advertisements inserted by webring which I find very offensive. Especially when I am touring a gay site and suddenly find myself redirected to pages covered with nude women. The actual traffic the ring has brought to my sites in the last 12 months has been under 15 hits. I probably have sent them many more of my visitors by hijacking than they have given me via the rings. So I am no longer affiliated with any of the webrings.