Apparently Mr. Gyllenhaal was ahead of his time and was doing the whole “gay cowboy” thing before the hipsters jumped on the fade making it trite. He’s also ahead of his time by professing his being ahead of his time on his t-shirt. This is like meta fashion bragging…almost the opposite of the overweight chick in the purple valor suit with “Juicy” on her ass.
I think this honor goes to the guy from The Village People. He was truly a gay cowboy before it was cool.