For decades the two characters existed in parallel—helping their mentors in fighting crime, providing useful sounding boards, and expressing the emotions of young readers. Dick Grayson was a teen orphan living with Bruce Wayne. Roy Harper was a teen orphan living with Oliver Queen. And their paths never crossed.
In 1964 Robin began working with Aqualad, Kid Flash, and Wonder Girl as the Teen Titans. But Speedy was notably absent. Fans wrote in, asking why the line’s other long-time kid sidekick was being left out.
So Teen Titans, #4 and #11, featured guest appearances by Speedy. And in issue #19 he became an official member of the team—and also managed to score a date with Wonder Girl, thus distinguishing him from all the other teammates who had crushes on her. But not by much.
The Teen Titans series, aimed at a younger audience, never mentioned Speedy’s heroin troubles through the 1970s. Its writers tried sought other ways to set him apart from Robin: he and Wonder Girl remained a casual couple, and he was a bit more hot-headed. There was enough space between the characters for the series’ last issue to retroactively establish Speedy as a founding member of the team.
In the early 1980s Marv Wolfman and George Pérez brought Roy Harper back for occasional appearances in the New Teen Titans magazine, this time referencing his troubled past. Now working for a government agency, he joined the Titans in attacks on drug dealers. Those issues also portrayed him as an incorrigible ladies’ man just as Dick Grayson was entering a serious (and sexual) relationship with Koriand’r.
Finally, after Crisis on Infinite Earths Wolfman and Pérez added another layer to Roy Harper’s character. New Teen Titans, vol. 2, #21, revealed that he’d gone undercover [!] and had an affair with an international assassin named Cheshire. They’d even had a child together. Dick (now Nightwing) and Kory were having sex, but Roy was having unprotected sex with a villain!
Roy Harper had become DC Comics’s anti-Dick Grayson. Dick was charming, respectful, and monogamous. Roy hit on almost any woman he met, especially when he was on duty. Dick became the one member of the original Titans who never married or had kids. Roy did the kids part first and muddled through as a single dad.
Nightwing was the young hero who did everything more beautifully than anyone else, whom everyone trusted. Roy was the character who managed to screw up most of the time. He bounced among among crime-fighting identities: Speedy to Agent Harper to Arsenal to Red Arrow and back to Arsenal. He owed his co-workers money. He took over the Titans, and the team fell apart. He formed the Outsiders for Dick to lead, and made a stupid fundamental error from the start. Nonetheless, he kept going. The result was a far more compelling character, a favorite for some readers.
DC’s “New 52” universe wiped out the Titans’ past and left little time for Roy Harper to have worked with the new Oliver Queen. Nonetheless, it reintroduced Roy as “the worst former sidekick ever” in Red Hood and the Outlaws. That may not be the best treatment for him, but at least it’s better than the Cry for Justice/Rise of Arsenal miniseries of 2010, which were so poorly received they were quickly written out of continuity. And it does preserve Roy Harper’s distinct role in the DC Universe.