In the case of clock king he wouldn't be as obsessed as his focus is on time I feel, so she would either fascinate him or annoy him on an idealogical level. Holiday, he was a personal villain towards organized crime so he would probably either admire her or not be bothered (his holiday gripe was with Calendar man but in this continuity well)
So it is an impressive link, and I look forward to seeing how you go with this.