Un-rotate the data frame, convert labels to annotation, rotate data frame again, rotate labels to compensate by setting annotation Angle field in attribute table to 90.From Wendy H. on 5/5/08:To produce rotated anno:On the advanced settings utility check only the "produce annotation that is rotated when converting labels to annotation when the dataframe is rotated" checkbox.In the labelling options check the option to "rotate point and polygon labels when data frame is rotated."To produce horizontal anno:On the advanced settings utility check the "produce annotation that is rotated when converting labels to annotation when the dataframe is rotated" and the "rotate labels with data frame rotation" checkboxes.In the labelling options uncheck the option to "rotate point and polygon labels when data frame is rotated."The first setting, in the Advanced Settings utility, is on the "Symbols/Graphics" page, "Label annotation" section.The second setting is in the Labeling toolbar -> Labeling menu -> Options -> General page -> "Data Frame Rotation" option.