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I have given Leo much thought recently. Mostly because my 35 year old brother's name was Leonardo (but went with Leonard). Growing up I cringed everytime I said his name as I would invariablely get a giggle. We called him Leo at home but never took that nickname outside of the house- it was just too uncool. Len was the best we could do for my surfing aussie brother with a proponderous Italian name.

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..but this was way before Leonardo Dicaprio and way before 'o' became cool.

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Needless to say, I love Leo, I always have.