I asked this in the D&D discord, but I'll ask it here too. IYO, what D&D novels are worth reading? Age, obscurity, and setting aside, which ones are actually good? If it's part of a series, do I need to read the ones before it first? Is it worth getting through those to read and understand the good one later down the line? I'm currently reading Dragons of Winter Night. I've already read Dragons of Autumn Twilight, (from the avatar series) Shadowdale and Tantras, and then Pages of Pain (the odd planescape book). The Dragonlance ones I mentioned are a little difficult to follow with the many characters involved. The avatar series, maybe it eventually gets better, but I didn't really like Shadowdale and I don't remember if I managed to get through Tantras or not. I do recall that it was... rough. I tried the first Drizzt book. It wasn't doing much for me. The first book of the cloakmaster series seems interesting. I just never get around to finishing it for some reason. By the time I get back to it, I need to reread most of it to catch myself up. I don't know if my expectations are too high for the novels, they eventually get better and I'm not giving them enough time, or if I'm just reading the wrong ones. Thoughts or recommendations anyone? I really want to like the D&D novels, but I'm starting to get that some of them are obscure with good reason.

It's been a long time since I read any of them, but...

None of them are all that good.

Many of them are fine. They're entertaining reads, but nothing to write home about. If you want to read D&D Stories, you'll probably be entertained. If you're looking for great fantasy writing, D&D is not the place to go. (AFAIK, they never went the route of getting established authors to write their books, which is a thing I've seen in licensed fiction these past few years.)

A number are... not good. (IIRC, it was the cloakmaster series that broke me of my youthful habit of finishing every book I started.)

IIRC, I found Weis/Hickman, Knaak, and Salvatore to be the best authors they had, and I don't go hunting down any of their works these days. (With the Dragonlance books, the second trilogy is much stronger than the first, probably because it focuses on a sane number of characters and their relationships. With Salvatore, it probably depends on how much patience you have for Angsty Dark Elf.)

Obviously, your mileage may vary, but it doesn't sound like it does.

Dragonlance Chronicles was my favorite as a child and still as an adult.  I just read NPCs by Drew Hayes which is book one of the Spells, Swords, and Stealth series and enjoyed it enough to get book two which I'm reading now.

The first Drizzt trilogy is kind of a slog but I found it overall enjoyable. The Icewind Dale trilogy was much better and entertaining but after that I didn't feel a need to read more Drizzt; I love the character but I feel I'm good until Salvatore decides to stop writing lol. Dragonlance is always good. Anything by Ed Greenwood is good if you can get into his style but his writing is not everyone's cup of tea. The newer D&D books are alright, I liked them enough but definitely one-and-done. There are so many novels in D&D literature and really, only a few are solid stories worth the time. They're all not bad, they're just kind of...there lol. I long for a D&D book that's rich and on the level of something like Sanderson would write or even a nice grimdark-ish story in the style of Abercombie.

I enjoy D&D comics more so than the novels. The Baldur's Gate comics are a blast and probably my favorite D&D fiction. If you like comic books, definitely check out the Days of Endless Adventure and Nights of Endless Adventure paperbacks.

At the risk of reposting a write-up from a similar thread last year...

If you're specifically looking for recommendations, I can suggest a few Forgotten Realms novels that stand out - The problem you'll likely find, though, is that just about everything is out-of-print aside from some of R.A. Salvatore's Legend of Drizzt series, even then, I wouldn't be surprised if they were too, nowadays.

You've already had Salvatore's Homeland (Book 1) and The Crystal Shard (Book 4) recommended above, so I'll try to steer towards other authors.

First, Paul S. Kemp's Erevis Cale trilogy and its' followups, The Twilight War Trilogy and Godborn.
A reformed thief and assassin forced back into action when the found-family of nobles he's been serving are threatened. He is pulled into larger and larger plots as a chesspiece on the board between Mask, God of Thieves and Shar, Goddess of Darkness as the Sea of Fallen Stars and then all of Sembia are threatened.
Kemp writes evil deliciously. Whether it is the Sojourner's selfish disregard for the lives and wellbeing of others, the scheming of Mephistopheles, Archfiend and Lord of Cania or the nihilism and fanaticism of Rivalen Tanthul, Chosen of Shar and Prince of the Shade, you're always going to have villains that are thought-provoking, intelligent and willing to do truly despicable things to accomplish their goals.
His protagonists fall more in line with antiheroes - Jak Fleet and Magadon Kest perhaps being exceptions - Erevis Cale and Drasek Riven are characters who, by necessity, have to use darkness to fight darkness.
There's also several short stories that tie into the series, which give greater context to the larger plot and character motivations, which can be found in the Realms of Shadow and Realms of the Dragons anthologies. Erevis is also introduced in the Sembia: Gateway to the Realms series and is a primary focus in the Halls of Stormweather anthology and Book 2 of the series, Shadow's Witness. These aren't required reading but are heartily recommended.
If you like Salvatore's action and want to explore a different part of the Realms, Kemp's your man.
He would later go on to write Star Wars novels once Wizards of the Coast ended the Realms novel line.

If Drow are a must but you want to try someone other than Salvatore's Drizzt and Jarlaxle, then definitely don't skip on Elaine Cunningham's Starlight and Shadows trilogy. The focus is a young drow priestess - Liriel Baenre - and explores a different angle and power dynamic of Menzoberranzan's culture, before introducing Eilistraee and her faith, as well as an introduction to Rasheman, the berserker lodges and the wychlaran.
Elaine Cunningham *IS* the voice of the early Realms. She was a history teacher before she was a writer and she'll weave a tapestry of the realms, it's people and its' stories. If her writing style grabs you, then consider picking up her Songs and Swords, a five-part series that focuses on Arilyn Moonblade, the harper assassin and Danilo Thann, bawdy wizard and foppish bard.

If you need more dragons in your Dungeons and Dragons books, then Richard Lee Byers is your man with the Rage of Dragons trilogy. Wizards handed this man the 3.5 Draconomicon and gave him free reign to use as many of the creatures within as he could to as devastating an effect as possible - Dragons all across the Realms are succumbing to madness, Metallic, Chromatic, Planar, Gem and otherwise - None are safe.
This trilogy moreso than the above recommendations feels more 'D&D', there's a mixed party of eccentric weirdos who have to save the world and it is a great time reading it. 
Byers carried some of his characters over to his next trilogy, The Haunted Lands, which had a focus on the Undead (And the Libris Mortis undead sourcebook that had just been released!), the politics of Thay and the overthrowing of the other Zulkirs by Szass Tam to bring the Thayan nation under his dominion.
And some of those characters would carry over into his five-book series, The Brotherhood of the Griffon, which follows a mercenary army as they struggle to exist in the Eastern Realms after Thay's fall and become entangled in plots of cults, gods, sky pirates and barbarian kings.
Look, It's... A journey. I promise you'll have a great time with it though and it'll cover more of the larger scope of Dungeons and Dragons than Drizzt fighting orcs for the umpteenth time.

If fiends, tieflings, warlocks or dragonborn are your thing, then Erin M. Evans' Brimstone Angels series is absolutely worth checking out. The six book series (One title, The Adversary, is part of the Sundering, a seven book set with each release focusing on a different author's characters during the transition from 4th to 5th edition, Kemp's Godborn is included in the same set) follows twin Tiefling sisters Farideh and Havilar with their adoptive father, the Dragonborn Mehen. Farideh finds herself trapped in a pact with the devil Lorcan, and the sisters find themselves caught in the plots and politics of both the kingdom of Cormyr and the Nine Hells themselves. Stolen divinities, Archdevils and the thrones of Cormyr and the dragonborn nation-state are all in play. While more recent than most of the other books listed, they're famously hard to get ahold of, but very worth the read.

But what if you're into Lovecraftian aberrations, otherworldly madness and Far Realm horrors?
Bruce R. Cordell's got your back with The Abolethic Sovereignty trilogy, continuing the elements and plotlines of his standalone releases from the Wizards (Darkvision), the Priests (Lady of Poison) and the Dungeons (Stardeep). While again not mandatory reading, the standalones give the complete story of the Raidon Kaine, monk of the Cerulean Sign, The Blade Cerulean and the ancient keepers who tried and failed to protect Faerun from the Abolethic Sovereignty and the horrors of the Far Realm.
The titular trilogy itself focuses on Raidon Kaine, the fey-pacted warlock Japeth Donard, the dream-shaping young noblewoman Anusha Marhana and Thoster, your crusty Lovecraftian sea-captain with blood-ties to something awful as the floating obelisk-city of the ancient aboleths rises out of the Sea of Fallen Stars, and with it, the slumbering Eldest - whom if awoken, can open reality to the Far Realm's horror.

There are so many other Realms novels that I'm dying to recommend, so if this listing is at all helpful to anyone, say something and I'll put up even more.

I'll take all the recommendations you're willing to tell me about. You don't even need to limit it to the realms either. Dragonlance, Eberron, Greyhawk, etc., any setting is good.

I read a lot of these when I was a teen. I don't think any of them are exceptional but the more enjoyable ones, from my recollection:

Elaine Cunningham, especially the Arilyn Moonblade/Danilo Thann books

RA Salvatore, mostly loved for Drizzt but I'm a Cadderly man myself.

Dragonlance: Chronicles was big and epic but Legends did a lot more character work and was, I think, much better.

Elminster in Myth Drannor. Daughter of the Drow.

Clicked on this topic more because I'm curious about the answers than because I have much to contribute, but my two cents on the books I've had occasion to read so far:

I've been poking at Keith Baker's Dreaming Dark trilogy, the first Eberron novels, because I love the setting. It's not the most stunning plot or characters, but the books have a lot of fun bringing out examples of all the cool setting details that are described in the sourcebooks, so I imagine that if anything it might be more exciting if you're not already into Eberron and more of the worldbuilding information is new to you?

The other thing I read is the Dark Elf Trilogy; wasn't too impressed there myself. The middle book was the best of the three, but no better than okay, I think. I kind of like some of the Underdark worldbuilding, not so much on Drizzt being the super special best person and swordfighter ever who's just kind of naturally awesome from birth in a world of mostly one-note baby-eating monsters; Exile was better since Belwar and Clacker gave it something resembling an actual supporting cast and Jarlaxle was a bit more complex than most of the other Drow. I barely remember Sojourn other than that goofy Roddy McGristle guy (I looked it up and I swear that is his actual name) Salvatore was trying to pass off as a main villain. Might give Icewind Dale a chance on the basis of the books livening up best when there were more characters getting focus, but I can't say I'm much of a fan of what I've read.

Quote from LancelotB >>

Dragonlance Chronicles was my favorite as a child and still as an adult.  I just read NPCs by Drew Hayes which is book one of the Spells, Swords, and Stealth series and enjoyed it enough to get book two which I'm reading now.

I've listened to the first three of the Drew Hayes NPC books on audio and they're great. They're very meta, and get more so as the series progresses, but that's to be expected of a series about four NPCs that have to go on a quest after the players all get TPK'd in session one

I have to admit I never read Dragonlance as a kid and trying to read them recently I'm finding them a bit of a slog. I'm getting on much better with the Drizzt novels and the more recent Fallbacks and Spelljammer: Memories Wake books were nice easy reads. The Critical Role books have all been pretty decent as well although your enjoyment of Critical Role will play a big part in that.

I actually have discovered NPCS. I think the premise is hilarious, but for whatever reason (probably because I'm one of those people who tries to read like 10 books simultaneously) I never got around to finishing it.

Maybe I should start a book club that's nothing but D&D novels. Any takers? I might make a seperate post now just to see if there'd even be enough people interested to try it out.

Outside of the popular ones every names, I really liked the King Priest of Istar trilogy, Lord Toede was hilariously funny.  So was Gully dwarves even though it started very slow. Minotaur Wars, Ogre Titans and Elven Exiles were all very good and better than any of the main trilogies.

My personal favorite was the Prism Pentad for Dark Sun.

White Plume Mountain and all the Justicar novels after it were absolutely amazing.  Would highly recommend the audio books though.  The voice actor nailed it in a way that must be heard.

If/when you do re-read them, let me know if they're still as good as you remember!

I was listening to the Dritz books...

I have a lot of issues with the world building and the development of the Drizt character... that was a hardcore failure to actually explore the idea of someone raised in a vile culture turning good... instead he was a "saint" since birth basically... well except that he didn't have a moral issue with looking at a young girl and thinking she was exactly what he was looking for in a "soulmate".

After a while I just kept listening because it was like watching a disaster in process... That and I was learning what I shouldn't do...