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What's with Roy Harper and Jason Todd's friendship?
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The age gap isn't as pronounced now. You might consider Roy around 2 years older than Jason and they hung out a lot as the Outlaws. So for Dick/Nightwing, it's like if his childhood best friend started hanging out with his younger brother.
Wasn’t Roy the oldest of the original titans. And by the time Jason shows up dicks is in college. The age gap is 5 possibly 6 years them being friends at any point never made sense.
There's nothing to indicate that it's a 2 year age gap, afaik.
Yeah, nothing really there for the age gap. I just plucked that out based on the new 52 robin timeline.
Ironically this happened to me when my brothers best friend became my best friend after my brother moved away for college.
To tl:dr it, Jason, Roy, and Starfire hung out for a bit in New 52 Red Hood and the Outlaws after Roy kind of fell back off the wagon and Starfire.. got addicted to space heroin, kind of? It was a bad book, but the broadstroked version of it is that they all kind of relied on each other while they were each in a bad place.
Their ages were closer during the New 52, but while their actual ages have been restored post-Rebirth, they still canonically hung out and bonded, so they're still friends.
They aren't contemporaries, though they did retcon in some extra interactions between them during Jason's time as Robin. The Outsiders stuff is still canon, as is Roy being a Titan alongside Dick.
If you're reading Rebirth Green Arrow- there's a bit of fuzziness in a lot of early Rebirth stuff because authors weren't entirely clear how much the events of Rebirth were going to restore to the timeline, and how much they were allowed to change stuff from the New 52.
Weren't they both in Donna's substitute Titans?
Yes
In 2011, they had a series together called red hood and the outlaws that ran for quite a few years. And yes Roy was a Titan with Dick.
Jason is consistently portrayed as closer in age to Dick then Tim and has been since he came back to life. It doesn't make any sense but it IS consistent.