#5
Jason Todd
Released 1983
#4
Stephanie Brown
Released 2004
#3
Dick Grayson
Released 1940
#2
Tim Drake
Released 1989
Jason Todd
Released 1983

Jason Todd is perhaps the most infamous version of the Boy Wonder. Introduced in 1983, the character was almost a carbon copy of Dick Grayson when he debuted, except for his strawberry blond hair. Eventually, Todd would get more fleshed out to become the character that we know today.
Raised in a tougher part of the city (which is really saying something for Gotham), Todd grew up as a street-tough orphan. Famously, he first encounters Batman while attempting to steal the tires off the Batmobile. Batman, seeing a great deal of potential in the boy as well as the possibility of him turning into a criminal, decides to take him on as the second Robin.
Todd's turn as Robin was unique in that he would curse, smoke, and often ignore Batman's direct orders. This Robin had a number of failures and victories during his tenure, but he and Batman were never fully comfortable with one another. Todd would tragically lose his life at the hands of the Joker, in a story that still shocks fans to this day. However, because this is comics after all, his condition would later improve. In the end, while Jason Todd ended up helping Batman on a number of important cases, he would later find his true calling as the Red Hood.
#4
Stephanie Brown
Released 2004

Speaking of Robins with turbulent journeys, Stephanie Brown isn't too far behind in that category. Debuting in 1992, the character was introduced as the daughter of Cluemaster, kindly described as a third rate Gotham villain. Brown began her crime fighting solely to "spoil" the attempted crimes of her father.
After successfully leading Batman and the Tim Drake version of Robin to her father's arrest, she decides to become a full-time hero. She starts running into Robin frequently and, eventually, the young heroes become a couple. During this time, she would begin training under heroes like Batgirl and the Birds of Prey. Even with her new training, Batman still wasn't convinced with her abilities. He would reluctantly take Brown on as the new Robin, but she quickly found herself getting fired from the role and inadvertently igniting a gang war.
Many fans felt that this hero was never given a fair shake as Robin, but Stephanie Brown makes it to this spot on the list for her perseverance, strength of character, and an incredible desire to prove herself as a hero. Though she may not have convinced Batman of her heroic prowess as Robin, she would certainly do so later, after defying death, as the new Batgirl.
#3
Dick Grayson
Released 1940

Wait. Haven't we already covered Dick Grayson? Sure, but this is the version that most fans are probably familiar with. This Grayson grew up very much like his Earth-Two counterpart that we’ve discussed previously. He was the child of circus performers, and as a natural acrobat, mastered the techniques of his early trade. Eventually, fate would toss the young Grayson a tragic curveball that thematically matched the type of loss suffered by a young Bruce Wayne. Seeing these similarities, Wayne would become the young man’s caregiver, and Grayson’s world would be altered forever.
The two orphans would form a bond unlike any other Robin thereafter. Robin would fight the darkness of Gotham City with a joke and a smile, and in the process, he would help fight back the same darkness in Batman. Robin was the light in Batman’s dark world. Robin’s presence would help remind the troubled Wayne of what he was fighting to protect. At the same time, while Wayne could never truly get over the death of his parents, Grayson proved that it was possible to move on after such a tragic event, and live a happy life as a crime fighter.
When he reached his teenaged years, Robin formed the now-famous group of young heroes known as the Teen Titans. Eventually, he would tire of being known as the Boy Wonder, and traded in his identity for that of Nightwing. While Grayson could easily be number one on this list for being the foundation of this heroic legacy, he’s at number three because he only came into his own as Nightwing. Eventually, he would surpass that role as well, to become the new Batman. He proved to be so impressive as Batman that many fans would have preferred that he maintained that role for even longer than he did. Today, Grayson is about to go on a new adventure unlike any he has experienced before, but his legacy will continue to live on.
#2
Tim Drake
Released 1989

Tim Drake is the third character to officially don the red and green tights of Robin, The Boy Wonder. This time though, things would be a bit different. For starters, Tim Drake wasn’t an acrobat, or really much of fighter, instead relying upon his wit and intelligence. At an early age, he deduced the secret identities of Bruce Wayne and Dick Grayson, and sought out the role of Robin because he knew that Batman ultimately needs a Robin.
Though Batman hesitated at first, as he was still dealing with the loss of Jason Todd, Grayson ends up convincing Batman that Drake would make a worthy ally. After training with an impressive array of fighters from around the world, Drake became a new and improved Robin. This version of Robin proved to be so popular that he became the first and currently only Robin to support his own Robin solo series (not counting Stephanie's brief five issues).
For 20 (real time) years, Drake fought alongside Batman in his own unique ways. While he became an accomplished fighter, he always preferred using his keen detective skills before entering the fray. In addition to that, this Robin also had a number of vehicles and gadgets very much akin to the Dark Knight. Drake would eventually become known as Red Robin, and in one of his greatest victories, Ra’s al Ghul would refer to him as “Detective,” a title he had previously bestowed only to Batman himself.
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