e's no slouch in real life. But on canvas—his looks enhanced by some cerulean blue and an aspect of wry cunning—Laurence Tisch looks very important. No surprise, given that the co-chairman of Loews Corporation captains a conglomerate worth $10 billion (market cap). But on that winter morning in 1999 when he posed in his office for the portrait that now hangs at New York University, where he is a trustee, Tisch at times looked more preoccupied than powerful, glancing between the man painting him and the computers that tracked the tremors in his $2.1 billion fortune.

No hint of that distraction appears in the finished painting, nor any telltale signs of his current 78 years. It's a portrait you sense Tisch would have liked in wallet-size, or to replace the photo on his driver's license. It's that good, worth every penny of the $35,000 price tag. On average, that's what John Howard Sanden charges chief executives, socialites and other power brokers. Among those who've sat: Metromedia's John Kluge (net worth: $10.6 billion), SAS Institute's James Goodnight ($4.6 billion), Citigroup's Sanford Weill ($1.6 billion). Sanden is currently painting Aetna head honcho Dr. John Rowe.

Sanden is one of a dozen or so portrait kingpins who charge around $25,000 for a head-and-shoulders oil and up to $50,000 for a full-body portrait. The best, such as Everett Raymond Kinstler, in Manhattan, have a waiting list of up to two years. (A portrait of AIG Chairman Maurice "Hank" Greenberg and his wife, Corinne, shares studio space with sketches of a dapper Tony Bennett and a stiff-lipped Bill Clinton.)

Despite market woes, professional portrait artists aren't pawning their palettes to pay the rent. Last year Manhattan's Portraits, Inc. found commissions for some 300 portraits. This year it'll be closer to 200, with middle-tier artists charging on average $10,000 a pop; the gallery pockets 40%. "We're recession-proof," boasts owner Marian MacKinney. Maybe because Silicon Valley—with its here-today, gone-next-quarter upstarts, never was a serious chunk of the corporate portrait business. "We haven't had one dot-commer. They don't stay in one position, or in one place, for too long," says MacKinney.

The resistance also has something to do with the crusty, dour reputation still dogging the profession. When John Singer Sargent, the Rembrandt of modern portraiture, unveiled "Madame X" in 1884, he nearly wiped out centuries-old codes dictating a subject's pose and demeanor. His depiction of a bare-shouldered Paris celebrity in a size-too-small black gown was a stick in the eye of tradition. But try explaining that to the Brooks Brother seated in the studio with a $25,000 check in his pocket. What the client wants, the client gets. "When I just started out I wasn't feeling pressure. I was just having fun," explains Sanden. "Now my clients are more conservative, and I'm more cautious."

That's precisely why portrait artists often feel slighted by the artistic community at large. There's no real mandate to create a work of art—just a contract to create a well-crafted, preferably appealing likeness of someone wealthy or important enough to demand one. That was once good enough for such masters as Hans Holbein the Younger, who immortalized many of the big-league hitters in the court of Henry VIII.

To liven up an uninspired portrait, Sanden will add a flash of color to a tie or a barely-there smirk, as in Tisch's portrait. Such touches illustrate why choosing a portrait artist is as important as selecting a good plastic surgeon. An error in judgment can yield a lifetime of regret. It's worth soliciting recommendations from other chiefs at the clubhouse or calling a gallery specializing in portraits. The Portrait Source, in Hendersonville, N.C., for example, represents 50 artists across the country and offers recommendations based on the subject, how much you're willing to pay and where the painting will hang.

Ask how much sitting time is involved. William Franklin Draper, the so-called dean of portrait artists, who painted a short-sleeved John F. Kennedy for the White House, requires three mornings. (Kennedy later insisted on being portrayed in a jacket.) Most artists ask for at least two sittings for two hours or so. Cancel the board meeting and forward all calls to your assistant. "He can take a call as long as it's from the White House," says Sanden, who made the exception only once, when then-Riggs National Corp. chairman Joe L. Allbritton took a call from President George Bush in 1992.

Some artists won't do posthumous portraits—or paint from photos. Last year Bill Gates commissioned Margaret Sargent to paint his mother, who died in 1994. Gates and his father gave Sargent photos and home videos of family gatherings. But painting a seated Mary Maxwell Gates proved challenging, so Sargent herself donned a suit and pumps and posed for photos to work from. The results were imperfect and required reworking. "They suggested that I change the color of her shoes. She always wore the same color shoes as her suits. And they told me that she didn't wear nail polish," says Sargent, who is related to John Singer Sargent through marriage.

Ex post facto changes are common, and upper-echelon artists are adept at finessing sore spots like a receding hairline or an advancing paunch. Other tips: Request that a mirror be set up so you can watch the painter in progress—and that you be allowed periodic peeks at the unfinished work. Be explicit about how large the painting should be (no larger than the company's former chief executives, typically with similar framing). Sanden recalls how he delivered a portrait to a retiring chief, only to learn that it was a lot larger than the company's other portraits. The solution? The client insisted Sanden paint his predecessor the same size.

The costs of corporate portraits are almost always borne by the company despite lagging sales or stock slide. (Though you can bet the expense is rarely mentioned at the annual shareholders' meeting.) Still, if the board of directors throws cold linseed oil on your plans, consider hiring an upstart like Minneapolis-based Steven Levin, 37, or award-winning Sacha Mobarak, 22, of Brooklyn, N.Y., both of whom charge as little as $5,000 a head. Or hire someone unrepresented by a gallery, like Simmie Knox, the Silver Spring, Md. artist recently commissioned to paint the official White House portrait of Bill Clinton. Knox, who has painted portraits of Supreme Court Justices Thurgood Marshall and Ruth Bader Ginsburg, says he had to "touch up" the former President's watery eyes, irritated by the allergies that plagued him. Says Knox: "I believe at some point you have to flatter a person."