Bob Dylan put it best in his seminal song She Belongs to Me: "There’s no success like failure, and failure’s no success at all."

These words came back to me this morning while reading a profile of peachy galleriste (and my longtime East Village neighbor) Amy Smith-Stewart, by Alex Williams, in the New York Times. Amy grew up in Rye, studied art history at NYU, worked at Artnet (obviously the highlight of her career), apprentice-curated at P.S. 1, spent a few months working for Mary Boone, opened a space on the Lower East Side, represented Kate Gilmore before she was famous, apparently didn’t sell much, closed her gallery under the radar with mysterious messages on her website, started showing one-off shows in available spaces, did an exhibition on 128th Street in which nothing sold ("that’s not the point," Amy tells the Times), and ends up celebrated in the aforementioned Times, complete with winsome color pictures of herself, grinning like a slinky feline with a mouthful of canaries, on the day after Tom Ford’s purple Andy Warhol sold for $32.5 million at auction.

This is obviously a new take on the starving artist in the garret (Vincent van Gogh should have taken Amy’s correspondence course!), and it got me to thinking of other successful art-world failures I have known. I didn’t have to look far, remembering another longtime East Villager, artist Dan Asher, who recently succumbed, rather valiantly, to cancer.

Many was the morning that Dan would wait for me to emerge from my apartment for the AM cup o’ joe, so that he could attempt to harangue me about how his latest gallery representative was ripping him off. Dan’s MO was always the same: some prestigious gallery, seduced by his OK if a little derivative talent, plus his scruffy resemblance to Allen Ginsberg, was about to open a show of his new work. Dan would accuse the gallery of stealing from him, often withdraw his work from the show and then expect me to trumpet the foul crime in print (which I am finally getting around to doing, now that he is safely in purgatory).

And guess what, like a Mississippi riverboat gambler, or some winsome blonde galleriste, Dan jumped from one prestigious art space to another. Paula Cooper showed him; Grant Selwyn Gallery gave him a great show when it was on 57th Street; Gavin Brown had him up at Passerby; Gavin Brown showed him in his West Village space; Gavin Brown even gave Dan a benefit exhibition to pay medical bills right before he died.

And Dan took their money, cruised off to the arctic to photograph icebergs and to Cleveland to photograph wrestlers, bitching and moaning (mostly to me) the whole way. There is a baseball player named Milton Bradley (his mother must have liked board games) who keeps getting traded from the Mariners to the Texas Rangers and, recently, to the Cubs. He is talented and he is, by his own recent admission, when he asked the Cubs to furlough him for counseling, "crazy."

Bradley has rushed into the stands to argue with fans and heaved balls, inappropriately, all over the field. And yet, baseball clubs continue to sign him up! It’s like the old story about the boy whose parents promise him a pony for Christmas and when he finds nothing but a pile of manure under the Christmas tree, he grabs a shovel and furiously starts digging, saying, "There must be a pony in there somewhere!"

As for the lesson here, I’m sure there is one. But I’ll be damned if I know what it is!

CHARLIE FINCH is co-author of Most Art Sucks: Five Years of Coagula (Smart Art Press).