Here's a good one, how about Jim Gordon interacting with superheroes that aren't Batman or a Robin (or any one-time Robins). Extended Batfamily counts, so Huntress, Spoiler or Cass are all fine, though those might iffy given GCPD's official stance on even the Batman. Superman, Wonder Woman, or any Justice League would also be delightful. Bonus points if you have any Jim with Babsgirl! (other than Legends of DCU 10-11, which have been posted already)