Time is the final arbiter of greatness, but the unprecedented prices commanded by artworks of late have given the personalities behind them such great fame that it is getting hard to say which matters more: the artist or the art. At times, it seems as if the oeuvre is merely a by-product of the charm. “Whether or not Damien Hirst is a good artist, he will have made a mark that history will record,” says the painter Sean Landers, whose ironic, self-aggrandizing canvases obsess on his nearly paralyzing anxiety over making art in today’s market. “Damien was a celebrity from that first show in London, ‘Freeze,’ in 1988, when Charles Saatchi bought the shark,” Landers says. “And he knew how to parlay that early success. Early successes of mine made me think they just hadn’t found out what a fraud I was.”

Hume, who took part in “Freeze,” says Hirst’s self-confidence is part of his attraction. “He finds doubt laughable,” Hume says. “So if you get involved with him, you can laugh and you can be naughty, and that’s a liberation. He disempowers the powerful. And that’s fun.” Hirst’s wealth and renown are now so enormous that it may be decades before history can determine if he is as great an artist as he is a market phenomenon. The same may be said for Richard Prince, who does not go out of his way to court the public but grants considerable access to his inner life through his writing.

The question is, how often does a work sell on the strength of an artist’s personality alone? “Most collectors are unaffected by artists’ personalities,” says Boone. “They only care about the art.” But Donald Baechler has observed just the opposite. Through his friendship with such collectors of his art as Yoko Ono, Baechler has been bumping up against celebrity ever since his paintings of dripping ice-cream cones and long-stemmed roses hit the market in the early 1980s. “I met George Condo then, and it seemed to me people were taken with him before they were with the paintings. Everyone was charmed by him. [The sculptor] Walter De Maria, on the other hand, was notorious for not showing up at his openings. It was always a puzzle how he got to be so famous without bothering to be there.”

The art world has its share of personalities who exhibit De Maria’s kind of inverse magnetism. Their diffidence, in fact, makes them as fascinating as uninhibited types. The New York dealer Matthew Marks, for example, may find it difficult to extend himself socially, but it doesn’t matter; with a roster that includes Ellsworth Kelly, Nan Goldin and Andreas Gursky, he has no trouble attracting clients to his four exhibition spaces. Then there’s the collector Charles Saatchi, whose discerning appetite for young art becomes more voracious each year. Saatchi hides behind exhibitions in his gallery and on his Web site, thus seeming to be everywhere at once, buying up the many while seen by the few.

Warhol was one of the past century’s most charismatic figures, a bewigged enigma who attracted crowds of the curious and paparazzi wherever he went. He galvanized not just artists and musicians but collectors and socialites, and his influence has only grown over time. Yet he spoke in monosyllables and revealed very little of himself. Like Koons, he disarmed through flattery, although in a different way. “Despite his fame,” says Colacello, “Andy would still ask for advice—should he use this wallpaper or not?—and he was accessible. You weren’t going to run into Jasper Johns or Cy Twombly in a nightclub. And even if you did, you wouldn’t hear, ‘Oh, hi! You should come up to the Factory and be on the cover of Interview.’”

For Mary Boone, “the underwhelming can become amazing, as in Ileana Sonnabend. Everyone always called her the Sphinx.” Jakobson remembers the sedentary, tent-dressed Sonnabend, who died last year, as “an enormous coquette—one of the sexiest women I’ve ever known. She could flirt with a doorknob. She had glinty eyes and a little giggle and was very passive. She drew people to her without even moving from her chair.”