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Yes this is definitely possible with a calculated field. Create a field called something like Column Tooltip Label like this:
If isnull([Comments]) then "" else "Comments: " end
Drop this new field onto the tooltip mark. Go into the tooltip editor and replace the current column label with this calculated field. Now when the comments field is null, the label won't appear.
Oh sure, just like this:
If ISNULL([Comments]) then "" else "Notes: " + [Comments] END