I think for boldness it was a guy at the Minneapolis Eagle, when I was in town on business. He moved over 2 stools to sit next to me at the bar, and without any word of introduction he reached his hand right out and touched my cheek, saying "Nice facial hair." I had a trim beard at that time.
I usually dislike being touched by a stranger, and my instinctive response was to be turned off by it. But he went right on to tell me how much he liked guys with beards like mine. And he was very good looking, my age range, nice voice, and made intelligent, pleasant conversation.
So, OK, I took him back to my hotel room with me where he stayed the night. Not the greatest guy in bed, but a bird in my bush is worth two in the bar. Is that how that goes?
We didn't do a repeat the next night when my business was again completed for the day, and in fact I went instead to the Saloon, where I found a different trick. In those days when I was traveling on the road & horny I considered "Hello" to be a good pick-up line.