Ryan Howard asks: "Based on the recommendation of Comic Books Are Burning in Hell, I picked up the two-part LOTDK story Masks out of a quarter bin. What are some other underappreciated LOTDK issues to buy this way? My annual con retailers have that series in droves. Alternatively, what are some other ridiculously cheap and easy to find comics issues that have been unjustly forgotten?"
Ah, an easy one!
The simple answer is that there was a lot of good stuff published in Legends of the Dark Knight over the book's almost-two-decades of existence. Even poor storylines still held some interest by virtue of the fact that most of the run had decent-to-great art. Even a terrible story like "Venom" still had Trevor Von Eeden on it, and that's more than enough reason to give it a recommendation. (It's still bad, though.)
Truth be told, I was never a regular reader of the book. I checked in periodically if something looked good - or, just as often, surreptitiously read it off the shelf. But there are still a few highlights I can recommend.
Kevin O'Neill appeared in the book a couple times, accompanied by Bat-Mite. Long before Morrison reintroduced the guy during R.I.P., Alan Grant and O'Neill were the first to smuggle the Silver Age imp into the post-Crisis universe, in LOTDK #38, and later in a stand alone one-shot called Mitefall, a pseudo-parody of the "Knightfall" storyline. Both of these were also recently reprinted in a thick paperback alongside the World's Funnest one-shot and a handful of other Bat-Mite (and Mxyzptlk) tales, and which is definitely worth buying
With issue #50 the series dropped its "Year One" conceit entirely by allowing the book to use Batman's real rogue's gallery. Issue #50 is a Joker story - and you guys know how I feel about Joker stories - but it's actually really good, one of my favorite featuring the character. It's another Dennis O'Neil joint, but this time with Bret Blevins, easily one of the most underrated artists of the last thirty years. I'm going to totally surprise you and recommend another Joker story, from a little over a year later - "Going Sane" by J.M. DeMatteis and Joe Staton, beginning in #65 and running for four issues. This one usually makes an appearance on any list of the best Joker stories, and it's also one of the few times to my knowledge that DeMatteis has written Batman. DeMatteis is underrated like Blevins, although in DeMatteis' case it's even more unforgivable as he has maintained a reasonably high profile in the industry throughout his entire career.
Doug Moench and Paul Gulacy later returned to the book with a direct sequel to their earlier "Prey," which just beats out the uneven "Gothic" as the best story in the book's early run; "Terror" ran for five issues beginning with #137. I'm going to completely ruin any credibility I have by finishing up by recommending yet another Joker story, "The Demon Laughs," which ran from #142-145. It's not a classic for the ages but it does have the Joker vs. R'as al Ghul, with art by Jim Aparo, and a story by Chuck Dixon. Dixon is a guilty pleasure, I suppose you'd say, and he wrote a lot of Batman in the 90s.
As for the rest of the run, at this point my sketchy knowledge runs out entirely. I know the book was published until 2007, but i don't even remember seeing it on the shelves. It looks like they were still publishing good stuff right up until the end - Seth Fisher had an arc in the book's second-to-last year, I see, and even up to the very last issue they had the likes of Christos Gage and Phil Winslade teaming up on a Deadshot story. And oh yeah, issue #200 had Eddie Campbell writing a Joker story for Bart Sears.
While it may not always have worked, LOTDK is still the gold-standard for these kinds of rotating-creator anthologies. No other character has ever been able to sustain this kind of book for long periods of time. Certainly, much of that has to do with the fact that Batman is Batman - but still, the attempt was made for a surprisingly long time to keep the book special. This was slowly eroded later on in the series' run when it began to tie-in with the Bat-books frequent crossovers throughout the 90s and early 00s - kind of hard to sell a book as an exclusive monthly event when you're selling part 178 of "Knightsend." But the commercial license afforded by putting Batman's name on the cover did allow creators to do some interesting stories which would otherwise never have had a home. It's a rare issue of the series that doesn't have something to offer.
As to the implied question of whether I'll ever return to write more about the series? We'll see. Long-time readers know that old features have a habit of resurfacing at the oddest times. I admit that I got bogged down in Mike W. Barr and Bart Sears' "Faith," wherein Batman enlists a street gang to help beat people up. I could have told you that was a bad idea, Batman, but you didn't listen.