Salamandyr
Adventurer
For instance, in 5e you can play an Outlaw Champion Fighter with Archery Style. That certainly evokes Robin Hood, just the natural-language meaning of it does, in spades. Champion, check, he championed the poor. Fighter, check, he fought in the crusades. Archery, check, he was a legendary archer. Outlaw, check, he robbed from the rich - it's all there. But does it actually model Robin? Not so much. He'll never split an arrow to win an archery contest, lacks woodsy skills, isn't any kind of a leader, and so forth. Leveling him up doesn't help. He does more and more damage, but his accuracy never becomes that remarkable, and he can't accumulate the broad range of skills he needs to be great at. 3.5 he might need to be a Ranger3/fighter4/ScoutX, with every class/level, feat and skill rank plotted out from 1-20, and be 13th level before he starts to live up to his hype, but he can get there, even if 'there' is strictly inferior to what the Tier 1s can do.
He'll never split an arrow to win an archery contest? Who says? That's just an attack rol against a high AC (I've run an archery contest in 5e where a character did this thanks to a really good roll). His accuracy is as remarkable as you want it to be--damage and hit roll numbers being translated into more and more precise shots.
Not having a specific "split arrow with arrow" ability doesn't mean it can't be done, it just means the ability is more abstracted. 3e was chock full of abilities like "split arrow with arrow" that meant, if you had specifically planned on having to do that, great, but if you didn't anticipate being in an archery contest, you couldn't do it at all.
Lacks woodsy skills? What's his wisdom? Is he proficient in Survival, Stealth, and Perception? If not, why not?
In 3e, if you've leveled Robin to be super good with a bow, how good is he with a quarterstaff? Or a sword? A 13th level warrior character ought to be death on two legs with any weapon, or none. In 5e he is. Sure, he's better with a bow (+2 accuracy), but he's happy to go rough and tumble with anything that comes along.
Granted, Grey Mouser, up to a point, works well with just the rogue class, thanks to weapon finesse, but Mouser doesn't rely on sneak attacks...at all. I can't recall a time in the stories he took someone out with a sneak attack. (EDIT: I just thought of one; Ill Met in Lankhmar. But then so does Fafhrd, and both could be described just as easily as an attack with surprise from stealth, no need for sneak attack dice) Rather, he's a master swordsman. In combat, he makes more sense as a fighter than a rogue. Now try giving him those thief skills in 3e with mostly fighter levels.
5e, not a problem. I've got a Paladin in my game that doubles as a rogue with no rogue levels. My own PC was a long standing fighter/rogue who I chose to make in this edition as only a fighter.
While no edition could necessarily completely emulate a fictional character, thanks to bounded accuracy and abstracted rules, 5e does it more easily, and more elegantly.
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