42 years ago - Oliver Queen is born
25 years ago - 17-year-old Oliver has an affair with a local girl in Tibet while on vacation. She gives birth to Connor Hawke.
20 years ago - 22-year-old Oliver is shipwrecked.
18 years ago - 24-year-old Oliver is rescued from his island, and begins using his new found skills to battle injustice as Green Arrow.
17 years ago - 25-year-old Oliver first meets Bonnie King, who tries to become his partner. He rejects her.
16 years ago - 26-year-old Oliver begins sleeping with Bonnie King, despite having no desire to take her on as a partner. He loses an archery contest to Merlyn, who then stages an assassination in Star City to win his position in the League of Assassins and severely beats him in the process.
13 years ago - 29-year-old Oliver takes in Roy Harper, and trains him to become his sidekick, Speedy.
8 years ago - while 34-year-old Oliver is away with Hal Jordan, Dinah Lance discovers Roy Harper's heroin addiction & takes him to rehab.
7 years ago - 35-year-old Oliver's relationship with Dinah Lance becomes more serious when her mother dies of cancer. He begins working with Helena Bertinelli, teaching her to use her crossbow.
6 years ago - 36-year-old Oliver meets his son, Connor Hawke. He stops Merlyn from killing Bruce Wayne, finally proving that he'd become the better archer.
5 years ago - 37-year-old Oliver sleeps with Helena Bertinelli. when Dinah Lance discovers them, she ends their relationship. He saves Mia Dearden from the streets.
4 years ago - 38-year-old Oliver is forced to kill Hal Jordan, and retires. his son Connor Hawke becomes the new Green Arrow.
now - 42-year-old Oliver runs for Mayor of Star City.
You really can't get a much more simple concept that a superhero version of Robin Hood. The character was clearly a reaction to the Silver Age Batman, with his trick arrows, Arrowcar, Arrowcave and so on. It wasn't until Neal Adams and Dennis O'Neil updated the character in the early seventies that he started to adapt his own identity. Rather than just modeling him visually after Robin Hood, he became an ideological equivalent to the character as well, championing decidedly liberal ideas that often conflicted with other superheroes who's methodology can, at least on paper, seem decidedly fascist.
It was a bold characterization, as comics were still usually treated as a children's medium, but it allowed a great deal of growth with the character and let him stand out among other characters even though his actual power set was essentially useless: he wasn't there because being an archer was an especially good power, but because he was a representative of an ideological perspective the team lacked otherwise. He was the one character that would fearlessly call everyone else out when he disagreed with them.
This obviously meant that he was often depicted as being deliberately antagonistic. Also, as his stories were used to depict real world problems, those same problems were often part of his narrative. His sidekicks were victims of drug abuse, HIV, and perpetual abandonment. His personal relationships were plagued with poor choices and infidelity. Oliver might have been a hero for the people, but he wasn't exactly a good person.
All of this is great. Some of the writers have tried to make him a sort of superhero James Bond: depicting him as a perpetually womanizing gentleman adventurer, but that was just playing into the idea of his misanthropy. Rather than try to write him out of it, we decided to embrace it all. This is who Oliver is, and who he SHOULD be.
Oliver was one of the characters that was replaced by a younger character in the early nineties, this time with his newly introduced son, Connor Hawke. Connor was cool, and was briefly part of Grant Morrison's JLA, but eventually, Oliver came back, and Connor was pushed to a supporting position. While we're not particularly interested in having Oliver die, we DO like the idea of Connor Hawke, and we decided to have him take over the role of Green Arrow by having Oliver retire after having to kill his best friend Hal Jordan. Hal's descent into Super Villiany is fantastic, and the idea of Ollie being the one that has to put him down is awesome. It opens the door for Connor to take over, while Ollie can focus on helping train Mia and on his new career as mayor of Star City. the idea of him running for office comes from a later series, and it's a great place for a former hero to go.