Most:
- Valor Bard is a fantastic Skald.
- Life cleric is the most old school cleric-y cleric there could be.
- EKs really feel like Lord-Soth style Death Knight Gish.
- Shadow Monks with shortswords are mystical ninjas. Once you can wrap your head around that not being a Rogue subclass.
- Beastmaster does a great job of "beast and master fight as one".
- Thief is a fantastic Thief-Acrobat with Expertise in Acrobatics, and if you want old-school thief Sleight of Hand, Stealth and Investigation.
- Wild Magic Sorcerers are lolrandom as heck if your DM refreshes Tides with a surge on every spell.
- but my top pick is Pact of the Blade Fey Warlock. Winter Knight.

Least:
- Trickery Cleric is probably the biggest fail for what people seem to think it should be. It's pretty good at being a defensively misdirection oriented cleric, but most people seem to want a Cleric-Rogue.
- Moon Druid doesn't really feel like a Druid, either old school, hippy, or shaman stand-in. Wild shape in general is a bad fit for Druids thematically, but Moon Druids lean in so hard they might as well be called the Shapeshifter class. They make a pretty good Injun Joe from Dresden Files if that's what you want.
- 4 elements Monks seemed to have missed the ElementBender mark most people expect of them. (Complaints about effectiveness often go hand in hand of course.)
- Vengeance Paladins feel nothing like 4e Avengers, which they're supposed to be the stand-in for.