Those words could so easily be used to describe the former studio head's marriage blanc to fashion designer and longtime friend Diane von Furstenberg. Diller's widely known to be gay; a former boy-toy even wrote a lightly-veiled account of his two-year relationship with a tycoon nicknamed 'Bear' who sounds much like Diller; and his for-show relationship with Diane von Furstenberg has long been the subject of amusement among Hollywood insiders.

Here's just one tale that makes the rounds. At Ed Limato's pre-Oscar party, Barry and Diane (who had just recently tied the knot with a lot of eyerolling from those attending) were hanging out. People were sitting with comedians Steve Martin and Martin Short. Short noticed Barry was there with his bride, and said, “Isn’t it a shame that Barry and Diane feel they have to be here swanning and glad-handing for political reasons when they could be at home doing it?”

L.G. But you’re purported to own the largest sailing vessel in the world now [the 300-foot-long Eos, for which Diller paid an estimated $200 million to build last year]. What’s that about? I mean, people have all kinds of theories on why rich guys buy big yachts.

B.D. I promise you, it’s not about size, it really isn’t. I mean, it’s not for me. I’ve had sailboats, and when I started to think about building a boat, I wanted to have a boat that had really good sailing characteristics and at the same time I wanted a boat that could hold my family and friends and be as comfortable as I could conceive it. And when we put those things together, it just dictated the length of the boat. It wasn’t backwards, like I said “I want the biggest boat.” It’s inconceivable that I’d say that. And I’m sure that at some point fairly soon I won’t have the biggest boat.

L.G: [Laughs] That's for sure!

B.D.: But I wanted a three-masted schooner. By definition it had three sticks in the air, it's going to be a little large, because that was the kind of sailing craft I wanted. It's not huge, Eos, and as a matter of fact one of the great things about it is its profile is not imposing, certainly not from some big white refrigerator. [Laughs] Big motor boats are usually white, and they're big, they're very imposing. That's not bad, but that's not my sailboat.

L.G.: If you like big white refrigerators!

B.D.: Whatever. Some of them are beautiful. But, you know, in this thing of boats, it's like planes. There's no justification for this, it's just I'm lucky enough that I got to build something that I had more fun than anyone deserves in building it, and now I'm having even more so in me and my family enjoying it.

L.G: Is that it for you, you think, in terms of being happy with this one for a while?

B.D.: No. I'm sure I'll get hungry for doing another boat as well at some point, another stripe of another kind. Once you're in boats, you either go bankrupt or you keep going.

[From Lloyd Grove's interview with the IAC boss]

• Ask. Diller said he planned to spend $100m developing and promoting IAC's flagship search engine. After an impenetrable advertising campaign, touting Ask's New Jersey algorithm, what's the impact on the search engine's market share? Nothing measurable. The chief executive, a Diller favorite, is out.
• Vimeo. Josh Abramson and Ricky Van Veen's College Humor remains popular among college students and those whose humor remains frozen in sophomore year. But IAC's bigger interest was the online video site, a precursor to Youtube, which the College Humor techies set up in the spare time. Vimeo creator and Julia Allison cheater, Jakob Lodwick, was fired late last year. Vimeo's traffic is hardly measurable beside Youtube.
• VSL (a highbrow email newsletter of cultural recommendations dreamed up by Kurt Andersen and Diller's content guru, Michael Jackson) is close to Diller's heart. "Without Very Short List, I would be much diminished," said Diller. Unfortunately, the internet as a whole would not be. Last time I checked, the subscription list was only some 20,000 people. (I'm told the base has grown several hundred percent since then.) Culturally-literate email-reading billionaires are in short supply.
• 23/6, IAC's stab at political humor with the help of the Huffington Post, is stillborn. Michael Jackson's other joint venture, a business site done in collaboration with Dow Jones, may never even get off the ground. Says one insider: "It's obvious it won't work somewhat from the outside but the inside scoop is zero progression/movement. As Sanchez (IAC's foul-mouthed head of corporate communications) might have said, just a lot of wanking."
• Lending Tree will be spun off for less than half the price Diller paid for it. This is not the best moment in the cycle to sell a mortgage broker. And the mogul did himself no favors by alienating Rich Barton, an IAC board member, who left aggrieved after Diller spun out Expedia, his online travel agent. Barton founded a competitor, Zillow.

IAC holds some prospering and substantial businesses such as Ticketmaster, the online ticketing site, and Match, the online dating exchange. But even these have been forced uncomfortably to walk in lockstep with IAC's other businesses, even when the logic has been flimsy. The unvarnished truth is that Diller, who built up Fox into the fourth television network for Rupert Murdoch, has a dismal track record in running internet businesses. No amount of Diller's brutal charm can obscure that.

What the mogul does have is the contrarian courage of a great investor, and a mastery of the dark arts of corporate infighting. He acquired e-commerce assets during the downturn, when other investors had written off the internet as a blip. And he's playing hardball with as much skill and ruthlessness as his disgruntled shareholder, John 'Darth Vader' Malone.

That raises the question. Why does Diller, a 65-year-old who enjoys his yacht and parties he throws with his hostess, fashion designer Diane Von Furstenberg, even pretend to run these businesses? He should not be the plucky entrepreneur fighting off the evil corporate raider. Diller is on the wrong side of that eternal conflict. He has certain skills and the temperament, just none suited to a managerial role. The detached and machinating capitalist played in the current struggle by John Malone? That should be, in the next business life at least, Diller himself.

• Here come the layoffs at the Philadelphia Inquirer. [NYT]
  
• The Times might feel confident enough that everyone's forgotten the whole Jayson Blair thing to ditch the Public Editor position altogether. [NYO]
  
• Gerry Levin's "inner poet" turned out to be some dude who runs a spa. [NYP]
  
• That Allbritton online politics thing scores another defection; this time it's Ben Smith of the Daily News, who snared yesterday's scoop on the stolen Giuliani documents. [NYDN]
  
• Radar's John Cook, Jeff Bercovici get all Woodward and Bernstein on some dude who wrote a mean thing in Brit Hume's Wikipedia entry. [Radar]
  

• Diane Sawyer's not going anywhere. At least until June. [NYT]
  
• Liberty Media's John Malone looking to pick up some Cablevision assets. [NYP]
  
• Union representing WSJ reporters and editors takes out ad in NYT lambasting its own paper. [WWD]
  
• Did the Times use a source who had an interest in the direction of the story he commented on? We're shocked. [Brooklyn Vegan, first comment]
  
• We hope Jon Friedman isn't as quick to pull the plug on his loved ones as he is on Katie Couric. [MarketWatch]
  
• WaPo's Richard Cohen makes HuffPo's Rachel Sklar fear for her decayingg ovaries. [ETP]

Ted Turner - Ah, Murdoch's first big American kill. One could lay the blame for CNN creator Turner's ultimate biz demise more properly at the feet of Time Warner, but Turner vs. Murdoch was too classic a matchup not to believe in. The conservative, rapacious Australian tabloid mogul versus his bizarro-world counterpart — an American redneck news hawk with liberal, philanthropic delusions of grandeur. These days, Turner can only seethe about Murdoch's lack of charity, when it's pretty certain that Turner would be more than willing to cross the street to kick him.

Dennis Potter - The grim reaper's touch has placed the caustic British TV dramatist beyond Murdoch's vengeful reach. That must be particularly galling, since in a 1994 interview shortly before his death, Potter famously noted that he had named his cancerous tumor after Murdoch.

John Malone - Perhaps the first serious challenge to the Murdoch family's dominance of News Corp. came via John Malone's Liberty Media. The American company had amassed a considerable though not yet controlling stake in News Corp., which Murdoch interpreted as a threat; Malone's complaints about Murdochian "empire building" at the expense of shareholder return also didn't help. The threat evaporated with a deal trading the News Corp. shares back as part of an $11 billion asset swap, including the transfer of a controlling interest in DirecTV over to Liberty. Malone and Murdoch are talking sweetly of each other and the deal now, but the Malones are probably off the Christmas card list for a year or two, at least.

Sir Richard Branson - After his NTL cable company lost its bid for commercial broadcaster ITV to Murdoch's British Sky Broadcasting, Branson called Murdoch a "threat to democracy" and agitated for a government breakup of News Corp. — or to put it in terms Murdoch would understand, a "regime change." Branson is yet another flavor of billionaire wackjob in his own right, and his knighthood can't make the famously establishment-hating Murdoch love him any more.

Silvio Berlusconi - Murdoch has been tangling with Italian media boss and former prime minister Berlusconi for quite some time, and the former's dogged persistence has brought growing penetration of Italian media. Add that to Berlusconi political downswing and his propensity to collapse on camera, and Ruperto looks buonissimo by comparison.

Kerry Stokes - A not-so-miniature Murdoch in the making, Stokes controls Australia's Seven Network, which has already tangled with News Corp. over a failed channel meant to compete with Murdoch's Ozzie properties. Stokes and Seven are on the rise now though, after opting into a AU$4 billion joint venture deal that frees up lots of cash for acquisitions and new launches.

George Michael - Called Murdoch "the devil" and a "media dictator." Michael claims Murdoch is out to get him, but the pop singer may launch a vicious retaliatory strike at any time.

Judith Regan - More on the shit list than the enemies list, due to the whole OJ book thing. But it's very easy to get promoted to enemy status, by way of something relatively innocuous, like say, a lawsuit. Developing.

[Photo: Getty]

• Evil, Inc.'s Rupert Murdoch and Liberty Media's John C. Malone kiss and make up. [NYT]
  
• NYT's Sulzberger tells investors to lick his left one. [NYP]
  
• Ugly rumble at Jane editor Brandon Holley's fortieth birthday party. Happy Birthday, Brandon! [WWD]
  
• Mickey Kaus takes time out from mocking Andrew Sullivan and Markos "Kos" Moulitsas to resume his long-running attack on CNN's Jonathan Klein. [Kausfiles, second item]
  
• Newspapers tell readers what they want to hear. Which, in the Times case, is that women have small dogs. [NYT]

• Subpar oral-sex provider Dave Zinczenko's advice book for the ladies isn't exactly licking sales charts up and down until they achieve climax. (Sorry.) [Radar]
  
• Very touching tribute to CNET's James Kim. [CNET]
  
• Andy Rooney's not a racist. A doddering old crank, sure, but not a racist. [CBSNews]
  
• How much does it cost a celebrity to keep a picture of nose-pickage out of the papers? About $10.5 grand, if you're in Italy. [Guardian]
  
• An idea so tacky we're shocked we didn't think of it first: Who's the hottest media wife? [MWD]