It isn't easy being a sidekick.
I don't know if it's cool for me to try a list where the five entries represent the only possible choices but oh well, here I go.
Not counting stuff like alternate timelines and the like, canonically, there have been five characters to officially hold the title of Robin, Batman's sidekick. Thankfully, all these characters are fairly distinct from each other and brought different traits to Robin's mantle. As I said, these five are also the only five but I still think this list has some merit because I really made the effort to decide which was the absolute best Boy (or girl) Wonder.
5. Stephanie Brown - first appearance: Detective Comics #647 (1992) as Robin: Robin #126 (2004)
The Robin with by far the shortest tenure and therefore the least impact, the girl formerly known as Spoiler was basically a fill-in for Tim Drake after his father discovered his secret and ordered him to give up the cape. She actually takes his place sort of out of spite. The two had been enjoying one of those always fun on again/off again teenage relationships and were once again on the downswing. So in her anger and frustration, she breaks into the Batcave and demands the Robin gig from the Dark Knight himself.
Batman never exactly approved of her activities as Spoiler and was reluctant to allow her to be the new Robin. But I guess he decided that he could keep an eye on her this way and train her himself. But it doesn't go well as she disobeys his orders on two separate missions and he's forced to fire her. Maybe it was Batman's inexperience when it comes to dealing with girls that led him to dismiss her in...not the best fashion. What I'm saying is that she didn't take it well.
So what was her next move? To show both Tim and Batman that she did have what it takes to be a great crimefighter of course. She would prove that she was good enough for their little Bat-club. Unfortunately (hello, understatement), her actions wound up starting a city-wide gangwar that cost many lives (War Games), including, apparently, her own, at the hands of Black Mask.
It would turn out that she did survive this encounter (although she was certainly brutalized and tortured) and would eventually become the new Batgirl after Cassandra Cain quit. But I guess that's going to be almost as short-lived as her stint as Robin what with the newest DC reboot reinstating original Batgirl Barbara Gordon (retconning away her paralysis, apparently). Now I wonder if Stephanie herself is going to survive the retcon.
Daughter of the Riddler rip-off, Cluemaster, I've always had a soft spot for her (yes, I have a thing for damaged girls) but can't say she wasn't the worst Robin.
4. Damian Wayne - first appearance: Batman #655 (2006) as Robin: Batman and Robin #1 (2009)
The biologically "perfect" offspring of Bruce Wayne and Talia al Ghul, Damian is the latest character to wear the R on his chest. Raised by his mother and his grandfather's ruthless League of Assassins, he's given the job at the age of ten. After such an upbringing, the biggest lesson he had to learn from his father and Dick Grayson is NOT to kill. And to not be such a little snot.
Teaming with Grayson, who took on the position of Batman after Bruce Wayne's "death", Damian remains a work in progress. Since his time as Robin is still ongoing at the time of this writing, I don't really have any more to say about him. Whether he's informing Dick that he doesn't have to listen to him, or treating Alfred like he's nothing more than hired help (he coldly addresses him as "Pennyworth"), Damian can be difficult to tolerate at times. He certainly has great potential and has already accomplished some pretty impressive things but he still has a long way to go.
3. Jason Todd - first appearance: Batman #357 (1983) as Robin: Batman #368 (1984)
Now here's a guy who proved to be so unpopular that the fans actually voted to have him killed. Although, to be fair, the margin was slim. Still, Jason Todd just had a way of getting on everyone's nerves.
It was time for Dick Grayson to grow up and become his own man. After spending his adolescence fighting crime with Batman, he was experienced enough to go solo as Nightwing (although he would often work as a Teen Titan too). In time, the post of Robin was filled once more. In his original incarnation (that I really know almost nothing about), Jason was more or less accepted by the fanbase. But DC's reboot following Crisis On Infinite Earths changed his origin and character considerably. Mostly under writer Jim Starlin, Jason became an overly angsty, impulsive young man. A street orphan who first encounters Batman while trying to steal the tires off the freaking Batmobile.
In many ways, this wasn't a bad way to go. There wasn't much point just replacing Dick Grayson with a carbon copy after all (which is basically what he was before the retcon). The fact that Jason wasn't a prodigy like Dick and was...a little rough around the edges, was a welcome change. It created a different dynamic for the Dynamic Duo.
But after awhile, everyone was sick of his attitude. His constant clashes with Batman led to an overly aggressive and reckless crimefighting style. At one point, it's strongly implied that he pushes a rapist off a roof to his death. This eventually leads to a big mess that nearly gets Batman killed (Jason saves him) and a whole bunch of criminals die. There's nothing wrong with introducing a bit of edginess but using Robin to do it just doesn't feel right.
By 1988, the second Boy Wonder had worn out his welcome with the fanbase and they voted for him to be killed off in the A Death in the Family storyline. Following a tip to discover who is real mother is, Jason runs off and eventually locates her in Ethiopia. She turns out to involved in an embezzlement scam with none other than the Joker. Jason is savagely beaten by the Clown Prince of Crime and he and his mother are left tied up in a warehouse with a timebomb counting down. Comic fans did their thing and voted for him to not survive and he bites it in the explosion as Batman arrives too late to save him.
Looking back on it now, Jason's most significant contribution to the mantle of Robin was dying on the job. It gave Batman even more reason to be brooding, self-hating and slow to trust others. He always recalls his inability to properly mold Todd and keep him from harm as his greatest failure - an echo that makes itself heard again and again in all Batman stories. His costume remains on display as a memorial in the Batcave.
Of course Jason's eventual resurrection and activities as the new Red Hood have no bearing on his impact as Robin. I rank him third mainly because he's certainly done more than Damian and Stephanie but also because his legacy as a tremendous loss affects Batman and those around him to this day.
2. Dick Grayson - first appearance: Detective Comics #38 (1940)
Surprised to see him here? What can I say - first doesn't always equal best in my book. Let's go back to the beginning, shall we?
When you think about it, it's kind of weird working out exactly what the point of Robin was. He didn't really seem to fit in. It was one thing for Captain America to have his teenage sidekick, Bucky, fighting alongside him against the Nazi Menace during World War Two. Plenty of teenagers certainly were involved in that conflict. And it was just a sign of the times that heroes during the Golden Age of Comics had young sidekicks working alongside them. Superheroes were originally aimed at an audience of children and the thinking at the time was that to help get kids even more excited about their favourite heroes was to present characters they could relate to. That way, it was even easier for them to imagine themselves sharing adventures with their comic book idols. So Robin existed to fulfill this need.
Here we had the Batman: the dark and mysterious protector of Gotham City, striking terror into the hearts of criminals by night with his relentless war on crime. Criminals are "a cowardly and superstitious lot" and his costume was designed to take the best advantage of that, giving him a psychological edge over the dangerous characters he opposed. But then there was Robin: an orphaned circus acrobat prancing about in bright yellow, red and green, making jokes. It kind of clashes with everything Batman's about, doesn't it?
But I realize that none of this is Dick Grayson's fault. He was merely the first in a line of characters whose very presence was a challenge for writers to explain. Why was the Dark Knight running around with some colourfully dressed kid? The easiest explanation was: to help balance him. Dick's upbeat and playful attitude served as a counter for Batman's serious and brooding manner. He's often reflected that at times, Robin's cheerful demeanour and carefree innocence (for someone in his position anyway) was the only thing that kept him from falling completely into the abyss.
So I realize I haven't said much about Dick's tenure as Robin. Well, that's because it would almost be redundant to do so. He was the first, longest-serving and easily most well-known character to hold the position. He was there for at least half of Batman's most celebrated moments. And he was great at the job, there's no denying that.
As he (very gradually, this is comic book time we're dealing in, remember) grew older, Dick occasionally began to chafe under Batman's tutelage. Towards the end, the fact that he was growing up and needed to become his own man became more and more apparent and finally, the Dynamic Duo parted ways. This was after about forty years of real time.
And my only real complaint regarding that time is that he actually was a little too perfect. Where his successor, Jason Todd, would prove to be overly angsty, Dick just wasn't angsty enough when you really think about how he grew up. True, unlike Jason, he had come from a loving and caring family who were raising him to be a good person. But I still think that he was just a little too squeaky clean as Robin and that keeps him from claiming the number one spot, as blasphemous as you might think that is.
1. Tim Drake - first appearance: Batman #436 (1989) as Robin: Batman #442 (1989)
So we come to number one with Robin Number Three. I know a lot of people believe that the best Robin is unquestionably Grayson but I just can't agree. And while Grayson is the most well-known Robin, Tim really is the one I grew up with. Yes, I watched Grayson on the amazing Batman The Animated Series in the early nineties and saw Chis O'Donnell play him in Batman Forever and Batman And Robin (shudder) in the mid nineties. But I was actually aware of Tim quite early on.
Somehow or other, I discovered the Knightfall storyline as it was going on in 1993 and in those pages saw that not only was Dick Grayson all grown up running around as Nightwing, but Tim wasn't even the next Robin after him. My knowledge of him trickled in gradually over the years until I got a clear picture of his character (remember, this was before I could just go online and look him up).
I think what struck me most about Tim was that Batman didn't actually recruit him. After Jason's death, he'd made a vow that there would be no more Robins. He of course felt that the whole thing was his fault. So how did Tim join the Bat Family? At the age of nine, using his own considerable abilities of deduction, he determined that the then current Robin was actually Dick Grayson after witnessing him executing a gymnastic move he'd used before when performing in the circus with his family. This led him to the logical conclusion that Bruce Wayne was Batman. In the wake of Jason's "departure", Tim eventually went to Batman and pretty much demanded the job. It was his belief that Batman would always need a Robin at his side.
I guess it was that he was a more cerebral Robin, displaying detective skills that might one day rival those of Batman himself, that most impressed me about Tim. Keep in mind too that he was the first Robin to actually star in his own ongoing title (uh, Robin). He was also the first Robin to operate in a cool looking costume (no pixie boots, for one thing) and, he was a nineties kid, like I was. Hey, how about that? The old Golden Age schtick of having a young character kid readers could relate to and envision themselves as actually worked on me some fifty years later. I don't know if that means Golden Age ideologies weren't all as lame as I thought they were or I was just a particularly lame kid myself...let's go with the first one.
Tim would go through some personal tragedy of his own, losing his father, rendering him an orphan, just like the Robins before him. He was also led to believe his girlfriend had died too, although we all know how that turned out.
Because I see him as a blend of all that was good about Dick Grayson and Jason Todd - not overly cheerful and wisecracking but not annoying angsty and moody either - and because he's clearly the smartest character to ever hold the gig, Tim Drake is the best of the Robins. History will prove me right.