From Superman’s Pal, Jimmy Olsen #91 and #92 by Leo Dorfman, Pete Costanza, and Mort Weisinger. Covers by Curt Swan with George Klein.
My copy of #91 is so warped it won’t scan properly, but you can still see that Jimmy goes all Scorpio Rising and joins a bike gang. He also pals around a bit with Robin. I think they had a lot of interaction in the Silver Age, but I’ve never read anything with them together post-Crisis. It would have been fun to see that relationship develop.