There are seventeen recognised Daedric Princes, and I'd argue maybe six of them are genuinely fascinating, a handful are wasted potential, and a couple are basically loot dispensers with a voice line. This isn't a power ranking or a "best artifact" list. Azura's Star is great, but that doesn't make Azura interesting. I'm weighing sphere, scheming, and whether the writers have kept them coherent from Daggerfall through ESO.
So here's my ranking, roughly best to worst, with the reasoning that matters.
The genuinely brilliant tier. Sheogorath sits at the top for me, and not for the obvious "haha cheese" reasons. Shivering Isles is the single best Daedric story Bethesda ever shipped because it actually interrogates its Prince. Madness and Mania as two halves, the Greymarch, and the reveal that the Madgod is the curse of Jyggalag worn as a man. That's a sphere with internal logic. Vaermina is criminally underused but conceptually razor-sharp: a Prince of dreams and nightmares whose whole game is that you can't trust what you experienced. Skyrim's "Waking Nightmare" is one of the few quests where the dread feels earned. And Hermaeus Mora. Knowledge as a sphere is dangerous precisely because it's seductive, and Dragonborn nailed the price-of-power theme with Miraak. Mora is the only Prince who feels like he's actually winning the long game.
The strong-but-inconsistent tier. Molag Bal has the best lore on paper, the first vampire, the planemeld, the soul-shriven harvest in Coldharbour, but ESO leans so hard on "evil overlord" that the subtlety drains out. Vile Manipulations should make him a chessmaster; instead he's a wall of menace. Mephala belongs here too. Obscurity, sex, secrets, and the Webspinner who founded the Morag Tong. That's a fantastic sphere, but she flickers in and out of being interesting depending on who's writing. Boethiah carries the same problem: deceit and sedition and the "good" Daedra of the Dunmer, yet quests reduce her to "kill the priest, take the shield."
The reliable workhorses. Hircine I respect. The Hunt is a clean, consistent sphere across Bloodmoon and Skyrim, and Sinding gives it a real moral wrinkle. Clavicus Vile is fun because the wish-granting trickster framing is genuinely playable, and Barbas is the best companion any Prince ever produced. Namira's repulsion-and-decay angle is grim in a way that lands when it's used. Azura is well-written but, sphere-wise, "dusk and dawn" is vaguer than her fanbase admits. She's interesting for the Nerevarine prophecy more than for herself.
The wasted potential. Nocturnal should be top-five. Night, darkness, the Twilight, the Evergloam, ownership of the Skeleton Key and the Thieves Guild. And yet she mostly shows up to be aloof. Sanguine is a great five-minute cameo (that Skyrim quest is iconic) but he's a sphere of one joke. Malacath's outcast-and-the-spurned theme is thematically rich for the Orsimer, but the writing rarely digs in. Peryite, Lord of Tasks and pestilence, is the most boring Prince in the canon and I'll die on that hill, "lowest of the Princes" is doing a lot of work.
The barely-there. Meridia isn't even technically a true Daedric Prince (Magna-Ge origins), and her anti-undead crusade makes her read like an Aedra cosplaying. Jyggalag is conceptually the most interesting idea, Order so absolute the others feared him, but he's only ever a backstory. And Mehrunes Dagon, despite headlining Oblivion, is a destruction battering ram with no inner life. Big, loud, dull.
If there's a through-line here, it's that the best Princes have spheres that create stories on their own, and the worst ones need a quest writer to invent a reason to care.
For lore essays like this I usually end up cross-referencing the wiki. The UESP Daedric Princes overview is solid if you want the primary sources.
So here's my actual question: which Prince do you think is the most misunderstood. Not your favourite, but the one whose sphere or motives everyone reads wrong?