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One of the best I have heard was, many years ago on shortwave radio I heard a commentator say................"With four furlongs to go Aspire Tee is still in front. How the hell it is, I will never know but alas it is. Doesn't say much for the rest of them!" Then on the corner the horse was still in front and he said, "Can you believe this ramble! They still can't get past this thing!" Anyway, the horse finally finished out of the first 4. From what I was told the commentator never called live again. All of us who heard him thought he was the best we ever heard.
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A former Tassie caller lost his cool one day when I was down there...I reckon that he, along with half the people on course that day, must have really unloaded on a 'promising 1st starter', pretty sure it was a 3yo actually but that's beside the point. Anyway, he called it bowling along, doing it easy in front etc & then when the push came on with a 1/4 to go it started to falter and inside of the final 16th it was in full reverse, the entire field went by and finished last. Old mate did his usual run down from the winner through placings and then back through the field until he got to the extremely well supported but dismal fav. whereupon he lined up on it with "...and someone had better go get (whatever its name was) a saucer of milk...'cause it's a CAT!" He was replaced soon afterwards but it was one of the funniest things I've ever heard on a racetrack. The owners did not find it funny however, no surprises there.