27 years ago - Jimmy Olsen born to a single mother in Suicide Slums.
14 years ago - 13-year-old Jimmy Olsen begins working at the Daily Planet as a gofer as part of a community service project. Lois Lane realizes how talented he is and gets him into the cub photographer pool.
13 years ago - 14-year-old Jimmy Olsen meets Clark Kent. he is the only photographer able to capture images of Superman, which run with Lois Lane's story, making him the youngest photographer to ever have images on the cover of the Planet.
9 years ago - 18-year-old Jimmy Olsen takes a full time job with the Planet, appearing on-camera in their remote TV spots.
7 years ago - 20-year-old Jimmy Olsen begins revitalizing the Planet's web division.
6 years ago - 21-year-old Jimmy is replicated by Rudy Jones to get into the Daily Planet to look for Superman.
5 years ago - 22-year-old Jimmy Olsen captures photos of Superman's death, winning international acclaim. He begins his own news feed through the Planet's Web
Jimmy has had such a weird journey over the years. There's so much content to draw from and a huge amount of it completely insane. Weirdly, one of the most innovative and forward thinking versions of Jimmy Olsen came in Grant Morrison's All-Star Superman. Instead of trying to describe it, I can use this exert of an interview with Morrison by the website newsarama:
"I don’t like victim Jimmy or dumb Jimmy, because those takes on the character don’t make any sense in their context. It seemed more interesting (sic) see what a young man would be like who could convincingly be Superman’s “pal.” Someone whose company a Superman might actually enjoy. That meant making Jimmy a much bigger character: swaggering but disingenuous. Innocent yet worldly. Enthusiastic but not stupid."
Granted, his Jimmy was also a prototypical Morrison character, which means he was clearly fueled by a steady diet of peyote, but the adventurous character was a innovative and bold re-imagining. Those qualities can apply to the character without making him quite such a weirdo.
Our take on Jimmy is also fueled by an understanding that the Daily Planet has to be more than just print media. Making it a large news conglomerate with a proactive web division means that the stuff Lois and Clark write actually matters (a man that can fly is one thing, but anyone caring about anything getting printed in traditional news is completely ridiculous). Jimmy's role as a photographer is a cool one, but if he's going to grow as a character he needs new mountains to climb.
It's also worth pointing out that Jimmy's signature look, at the time I'm writing this, has somehow come back into style.