Beloved legendary performers inspire the sort of dedicated fan base that hungers for everything they’ve ever done—even if it’s terrible. Actually, that’s a perk of being an enduring artist: Hang around long enough and eventually even some of your crap seems ingenious. To a certain degree, the enthusiasm for every last scrap of an artist’s legacy is flattering, an indication that sympathetic fans crave a warts-and-all portrait of the performers they admire. But it becomes more problematic when corporate greed and the ravenous demands created by the internet start influencing what we hear. Doesn’t quality deserve some consideration, too?

At the end of August, Columbia Records will unveil Bob Dylan’s Another Self Portrait, a multidisc collection that revisits the sessions that led to 1970’s Self Portrait, the album generally considered Dylan’s worst. Dylan was on a hot streak before he released Self Portrait, a curious collection of poky country-flavored covers, instrumentals and original tunes that spanned two records and showed little of the inspiration that had marked previous masterworks such as Blonde on Blonde and Highway 61 Revisited. Critics hated it. Reviewing Self Portrait in Rolling Stone, Greil Marcus began his pan with what became perhaps the most famous opening line of a record review: “What is this shit?” An attempt by Dylan to strip away the mystique hanging heavy on his shoulders by putting out intentionally trivial music, Self Portrait succeeded all too well in its mission, convincing many of the faithful that his moment as a generational spokesman was over.

Forty-three years later, that shit is now being celebrated. Columbia not only acknowledges Self Portrait’s abysmal reputation but is using it as a selling point. The advertising for Another Self Portrait proudly cites Marcus’s review and goes on to claim that this new set, which features alternate versions and unreleased songs from the late 1960s and early 1970s, “bring[s] fresh perspective to one of the artist’s most controversial periods and reveal[s] it to be one of his most wonderfully creative and prolific.”

Another Self Portrait is the latest example of an unpopular, infamous misfire being embraced years after the fact. (You can also see this trend in the recent wave of critical reevaluations defending notorious movie bombs such as Heaven’s Gate and Ishtar.) In an era when we’re beset with endless lists honoring the all-time-best movies, albums, songs, TV shows and everything else, these sorts of reappraisals serve as a backlash: Stop shoving your canon down our throat and let us discover things on our own.

Such an environment suggests that every piece of work, no matter its merits, will find an audience that can appreciate it. (And in fact, Another Self Portrait itself is part of a larger Columbia series of official “bootleg” Dylan albums, the label’s wise strategy to capitalize on the dozens of studio recordings and live tracks that never got released but circulated among fans for years.) But the truth is that there are some projects so terrible even their creators don’t want them out in the world.

Too bad for them: Audiences are going to hear an artist’s most embarrassing failures—either through labels’ greed or fans’ insatiable curiosity.

Dylan has experienced both scenarios—but not through Self Portrait. For although Self Portrait is remembered as Dylan’s nadir, it’s actually an album that came out three years later that’s really his low point. I’m talking about Dylan, a nine-song set of covers recorded during the sessions for Self Portrait and its follow-up, New Morning. On Dylan, you can hear the man warble Joni Mitchell’s “Big Yellow Taxi,” mangling the lyrics in the process. You can check out his “Lay Lady Lay”-like treatment of “Can’t Help Falling in Love With You.” They’re not wretched performances so much as exhausted ones—the sound of a guy kicking back and screwing around, safe in the knowledge that if he wasn’t pleased with the takes they would never see the light of day.

Except they did. Dylan was put out by Columbia, the same label now proudly hawking Another Self Portrait, after Dylan left to sign with Asylum. Undeterred by Dylan’s exit, Columbia decided to release a set of leftovers from his time with the company, figuring it’d squeeze every last penny out of its association with the songwriter. Dylan is one of pop music’s most obnoxious examples of corporate cynicism, preying on fans’ unquenchable thirst for their songwriting hero’s tunes.

Perhaps not surprisingly, Dylan is now difficult to find. It’s never been issued on CD in the U.S.; it’s not commercially available anymore; and tellingly, none of its songs show up on Another Self Portrait. (Dylan’s comprehensive website dutifully lists Dylan in his discography but doesn’t include any song snippets or purchasing information.) Yet you still can track down Dylan on vinyl through eBay or hear some songs on YouTube. What was once a money-grab for Columbia is now an online scavenger hunt for Dylan’s most voracious supporters.

Nowadays, no folly escapes the ether. Have you always wanted to check out Song of the South, Disney’s racially insensitive 1946 film starring singing, happy African Americans in a post–Civil War tale? Well, don’t let the fact that it’s never been on VHS or DVD stop you: You can watch parts of it on YouTube or bid on a rare 16mm print online. Similarly, we all know someone who boasts of owning the incredibly awkward late-1970s Star Wars Holiday Special, even though it has never been available for purchase. And just this month some footage from The Day the Clown Cried leaked, bolstering hopes that one day Jerry Lewis’s long-vaulted, never-released World War II movie about a clown forced to entertain kids on their way to the Nazi gas chambers will eventually be unearthed for mass consumption.

For as much as we like being familiar with the world’s greatest art—all those best-of lists exist for a reason—we’re also seduced by the dregs, especially when they’re kept from us. Being curious about the detritus of legends stems from a mixture of fascination and reassurance that even the most talented among us can screw up. Plus, because we’ve become used to obtaining just about anything we want online, it’s genuinely exciting to think that there are still some long-lost artifacts out there we can’t yet possess. Rather than discouraging us, that reality makes those artifacts more precious. After all, it can often be more satisfying to imagine what something sounds or looks like than to actually hear or see it. (In some ways, these objects are better—more perfect—because we can’t readily get our hands on them.)

But that ravenous craving carries with it some consequences. When a musician dies, his heirs (and label) will make a few bucks churning out posthumous discs that are often inferior to the work he did during his life. Not that rabid fans mind: For a while there, Biggie, Tupac and Jimi Hendrix seemed more popular on the album charts dead than when they were alive. But even when the artist is alive, the label (usually with the artist’s consent) will try to bilk fans with remastered “deluxe” editions of old records and greatest-hits albums that contain a few new tracks as bait. Rarely are these “bonus” tracks worthy of standing side-by-side with the performer’s finest moments. (And in the case of those remastered old albums, the extras are often rough demos or clearly mediocre unfinished offerings.) And yet there’s enough of an audience out there to keep justifying the industry practice, which happily dilutes an artist’s recorded legacy to satiate the public’s need for completeness.

In a sense, this battle between label greed and proactive consumer curiosity has always gone on in pop music. When Dylan sat down with the Band in 1967 to record some songs on a lark for what would eventually be packaged as The Basement Tapes in 1975, an illegal boot of some of those sessions came out as Great White Wonder in 1969. Ironically, at the time Columbia sent out a statement decrying the bootleg, saying, “We consider the release of this record as an abuse of the integrity of a great artist. By releasing material without the knowledge or approval of Bob Dylan or Columbia Records, the sellers of this record are crassly depriving a great artist of the opportunity to perfect his performance to the point where he believes in their integrity and validity.” Today we see that labels don’t mind infringing on an artist’s integrity just so long as they can cash in on it, too.

Nevertheless, whether through a label or more illicit means, we live in a culture that’s just as interested in the scraps as the main course. But if we’re not discerning, the blood, sweat and tears of artistic expression will just become digital stuff we’re all feverishly chasing down without thinking about its actual creative merits. Sometimes we get so wrapped up in figuring out how we can get our hands on something that we don’t stop to wonder if we really need it.

Tim Grierson is Playboy for iPhone’s critic-at-large. You can follow him on Twitter.