Ooohhh it's been many years, let's see how many I can remember.

I have a good speaking voice, but I'm not much of a singer. I can hold a tune ok, but my range is limited to an octave or so. It's deep, think Nick Cave.

I picked Nick, as I can duet the Wild Roses well.
New York, New York.
Base part of Blue Moon as a duet.
Ice Ice Baby (yep, there was a time where I could do the rap).
Anything by Bing Crosby (White Christmas was my go-to).