Which fictional detective is the most personally miserable?

At least in the stories (actually, story) Holmes only admired her for her cleverness.

-A Scandal in Bohemia

To all appearances Holmes was asexual, and happy that way.

I agree. I think that sometimes Monk is happy with all his peculiar quirks and tics.

I think that Columbo is very happy. He loves his job, he loves his car, his dog, his wife. And especially his raincoat. He’s one of the happiest of detectives.

DI Jack Lennon of Stuart Neville’s Belfast series.

The various Scandanavian detectives all seem to have bleak outlooks on life and the bleak lives to go with them. I would nominate Jo Nesbo’s Harry Hole (“The Snowman”, etc.) as the most miserable.

Stephen King’s Bill Hodges was pretty miserable.

Side note: Until Mrs. Columbo got her own TV series, there was wide speculation that Columbo didn’t really have a wife. You never saw her, and it was thought that making references to a nonexistent wife was one way of making the perp let his guard down.

Scooby and the gang seemed quite happy. Especially, Shaggy. What was in those Scooby snacks anyway?

But we’d see him telling other cops on the force about her at the end of an episode: after getting the perp to blurt out incriminating stuff, after which said perp was never seen or heard from again. Or, in the ‘vacation’ episode, we repeatedly saw a guy who works on the cruise ship flatly state that he’d seen her — including in the final scene, well after the perp had already been caught.

And et cetera, and AFAICT all before the other show ever hit the air…

Don’t kill the messenger. I’m just passing along the speculation.

I have the Monk DVD set and I’m just rewatching now. There’s one scene where he’s on a plane and this little kid plays a trick on him where the answer to a riddle is “repeat” (re-pete). When he gives the answer, the kid repeats the riddle. This goes on, over and over. Adrian knows he’s being manipulated, but his disorder compels him to keep answering. You can see on his face the turmoil of being at the mercy of his disorder and not being able to stop answering… Sometimes he seems “ok”, other times it just makes you want to cry.

He’s so annoying, I don’t know how anyone could stand to be around him. Buy he’s oblivious.

Two nominees:

Rust Cohle, from True Detective Season One, never said anything except bleak aphorisms that made you want to slit your wrists. Great show, but Jesus Christ, man.

Bernie Gunther, from Phillip Kerr’s eponymous series, lived through the Third Reich by going along to get along. He never commits atrocities, indeed investigates and even stops some atrocities, but also never forgives himself for being part of the evil of Nazi Germany. His gallows humor covers up a bone-deep self-loathing.

The Punisher. Some people might wish they were Batman, Green Arrow or Spiderman. Anyone wish they were Frank Castle?

That’s stretching the definition of detective a lot. But sometimes he does detective work to track down his targets. Call him a crimefighter.

Eddie Valiant wasn’t the same after his brother got crushed by that piano.

Andrew Vachss’s Burke had a miserable life and is not a happy person.

Xavier March in the Rober Harris novel “Fatherland” had some pretty awful stuff happen to him. He seemed contented with his moral victory, though.

Alec Hardy on Broadchurch spends the first two seasons in growing misery. I haven’t seen the third season.

Plus, on more than one occasion he’s been seen whistling his own theme music! Most of us don’t even have theme music.

Nitpick - she wasn’t his wife at the end of the very brief 13 episode run.

For detectives who are personally miserable, I’ll nominate Jeff Goldblum’s Raines. Raines saw dead people, but even he knew they were hallucinations. He feared the fact that he had them, feared anyone ever finding out (which would end his career as a detective) and feared he was actually going insane. The show only lasted 9 episodes, and I was worried that the only path for him was that he’d eat his gun.

Harry Bosch is such a miserable asshole that he succeeded in making me quit the whole series after about 5 novels.