You would think that Ron Burkle would lead a charmed life, considering all the perks he enjoys as a billionaire mogul. He flies around on a private jet! He cozies up to starlets! He hangs out with fellow horndog Bill Clinton! He secretly backs Radar, and has the best flacks money can buy to control his press coverage! But no amount of money will allow Burkle to have it both ways; he wants the parties and models, but not the notoriety that comes with them. Sorry Ron, you have to choose one or the other. Because when you're out bothering models and sharing girls with Leonardo DiCaprio, we hear all about it: In the Daily News' Rush & Molloy gossip column today, there was this about Dicaprio:

It turns out that frequently rehabbed former Insider host and overall smarmy dude Pat O'Brien is an underminer. And one remarkably lacking in self-awareness, at that! We really expect more from men with mustaches. See, Pat just got back from Iowa—he's "a little bit of a favorite son there"—and met the real people. To help them (somehow?), he decided to email this undermine-spirational message to everyone at The Insider and Entertainment Tonight:

You know how PR agencies are—always looking for a way to do some selfless charity work. So international PR machine Porter Novelli came up with a great idea: round up a bunch of its young staffers and offer their inexperienced services free to those who need it most: fashion companies, models, and Penn Badgley's mom. Paying it forward is what it's all about! The little "pop up agency" within PN is called "Jack and Bill," and it displays its digital new media online internet publicity chops with a microsite, Facebook page, and a Flickr page! Needy (heh) fashion clients had to audition to win the services of the eight young 20-something staffers. They graciously picked a lawyer-turned-stylist, an apparel company, a model, and this dynamic duo:

Boy, $300 million sure buys a lot of storytelling. Microsoft has released two more 90-second ads starring Jerry Seinfeld and Bill Gates, the Laurel and Hardy of... Microsoft ads. More than the first, totally mystifying "shoe store" ad, these new spots flesh out the plan: Bill Gates as lovable icon. He's like Joe Isuzu with a bad haircut! He does the robot! We're still skeptical, but it's progress. You can watch the two official ads here, but we like this version even more: all the footage of the two ads (and some extra that was edited out) in one four-and-a-half-minute long unfolding storyline. Trippy:

International playboy and fraud superstar Raffaello Follieri is no longer just an alleged swindler. As was rumored earlier this week, he pleaded guilty yesterday to 14 counts of fraud, conspiracy, and money laundering in connection with a Catholic church property investment scam. He had to give up $2.4 million, along with all that nice jewelry he gave to his charmed girlfriend Anne Hathaway. Next time give a poor man a shot, Anne! Now Follieri's personal grooming is paying the price for his foolish decision not to listen to Lizzie Grubman:

The Smoking Gun got hold of the FBI's list of jewelry that pixieish actress Anne Hathaway (referred to only as a "girlfriend" or "individual") had to surrender because her ex-boyfriend, holy swindler Raffaello Follieri, bought it for her with his fraudulent proceeds. He was very generous with other people's money! There are a dozen items on the list, which must be worth tens or hundreds of thousands of dollars. Money is no object when investors are paying unknowingly! The full list, Rolexes and all:

The ultimate confluence of a prestige media restaurant reviewer and prestige media restaurant has finally occurred: Frank Bruni has reviewed Michael's for the Times. At this point we should skip all the background, because those who don't appreciate the import of this moment will never be invited to Michael's anyhow. Suffice it to say that the city's most famous critic visited its most famous media power lunch spot, and, in a blinding flash of meta-media honesty, declared that it sucks big time:

Hip hop mogul and sophisticated ball waxer Puff Daddy got a little embarrassed this week, when some journalist-for reasons still unknown-decided to fact check something that came out of Puffy's mouth. Specifically, a rant that the millionaire bad rapper spit on YouTube about how he had to stop flying on his own private jet due to high gas prices. Then a gossip guy at the Palm Beach Post actually combed the records and talked to secret sources and discovered there is no private jet registered to Puffy or any of his companies. But there is an explanation!

The plan was for Track to be the good kid in the Palin family. The athletically-named son of VP nominee Sarah Palin—who's set to ship out soon for Iraq—was portrayed as a symbol of patriotism on stage at the Republican Convention. But did he only join the Army to escape a life of drugs and crime back in Alaska? The newly famous enlistee gets the full investigative treatment from the Enquirer —which always saves the best stuff for the print version. Which we now have in hand! The young man has partied with some very talkative people. So: while Track was watching his mom enthrall the nation, was he really daydreaming of mainlining sweet, sweet Oxycontin and playing "master" criminal back home? We quote: Track is portrayed as the biggest bad boy in Wasilla. A serious drug problem, vandalism, theft, and partying are his main pastimes, allegedly. Which really wouldn't be that remarkable if the Republican party wasn't holding him up as, you know, a role model. If true, this would make the Palins a caricature: the country family with a pregnant teen, son on OxyContin, and a mom desperately trying to present a respectable face to the world. And failing. And honestly, everyone: the Enquirer does not represent the media elite. So the liberal media should be safely insulated from the backlash on this one. The best quotes from the Enquirer's story:

Longtime ultimate fighter and former UFC middleweight champion Evan Tanner was found dead in the California desert yesterday. He had apparently become stranded without water and succumbed to the heat. Tanner, 37, always looked more like a mountain man or a brooding surfer than a brutal fighter. But he kicked ass with the best of them. He rose to fame along with his sport itself, and his crossover appeal—which was immense—will probably only increase as the full story of his death becomes known. Rest in peace, dude.

Less than two weeks after Microsoft confirmed that it had picked the Mac-loving Jerry Seinfeld as its new endorser, this ad with Seinfeld and Bill Gates is everywhere. And it is awful. I mean, it's kind of engaging to see this half-billionaire comedian kicking it in a shoe store with the many-billionaire Microsoft nerd-in-chief; but up until the final seconds, I was convinced this was an ad for Payless. And I may be stupid, but I'm still your target audience, Microsoft. Surely Sarah Silverman and Willie Nelson will be a bit more techno-centric. Watch what $10 million can buy, after the jump:

Controversy: A magazine has published a list of "Overrated" things! Is their analysis correct? They certainly hope you will argue about it a lot! Blender's list of the most overrated things in music ends with a typically "provocative" #1: Deceased rapper Tupac. Former Gawker columnist Tionna Smalls has already started an online protest campaign! Problem, though: Tupac is the most overrated thing to hit music since the synthesizer craze. It's the mythology that did you in, Pac:

Rob Shuter may be single most well-qualified man for his job in all the celebrity media. His job, of course, is editor of photo-happy, celebrity-friendly, "What interview questions would you like to answer, Britney?" pseudo-magazine OK! But set aside your revulsion at the existence of this pair of celebrity culture warriors, and you come to realize that we can all learn something from the way the man does business. His reputation is (grudgingly) improving along with his personal appearance (pic: old on left, new on right). Shuter told CoverAwards that his magazine is "celebrity-fair." Classic, classic. Break it down: Shuter was a celebrity flack before he came to OK. So when he got the job, some of the esteemed journalists at the magazine were angry at this publicist interloping on their territory. But really, a PR guy is much better suited to the job than someone with a history on the editorial side. The editor of OK essentially works to broker deals with celebrities and their managers and publicists. That was Shuter's gig before, on the other side of things, so he knows just how to make this work. His competitors, who came up as reporters and editors, will never have that experience. He could be functionally illiterate. No problem! Celeb magazines are driven by photos—exclusive photos. Who fucking cares what OK's brain damaged stories say? People want to look at pretty photos of famous people that they can't get anywhere else, and that's what they get from Shuter. Plus, appearance on shows like ET and Access Hollywood usually materialize only after the exclusive magazine deal has been closed, meaning that celebrities have to deal with one of the mags no matter what. And since OK is the friendliest and one of the most financially generous, bingo. Rob Shuter is a shameless man in a shameless job. Many lesser people would be embarrassed to be him. But Shuter can say with a straight face that he's "proud of the product" and dismiss competitors as "haters" and be totally genuine. He's worth every penny. "Celebrity-fair" is the new "right-sizing."

Nude supermodel photo scandal lawsuit alert! An anonymous model has filed suit in Miami against Egotastic.com and Splash photo agency for taking pictures of her sunbathing in her birthday suit (NAKED) in her own backyard—"as is often done by professional models to avoid tan lines." Invasion of privacy and emotional distress! But who is this mysterious, super-beautiful plaintiff? She helpfully includes several clues [UPDATE: the case may already be cracked!]:

Movie-like occurrence of the day: Pirates, for fuck's sake, have robbed a posh 178-foot party yacht moored off Corsica, making off with a freaking fortune. In the past the boat has hosted Jack Nicholson, Armani, and Puff Daddy, among others. Will the publicity surrounding this daring act of Robin Hood-style crime, minus the "give to the poor" part, lead to a rash of similar hijackings in the near future? You better believe it. Do you have any idea how lucrative yacht piracy is?:

A tipster has sent us five photos of brand new works by semi-secret superfamous street artist Banksy. All five were just put up in New Orleans, to commemorate the third anniversary of Hurricane Katrina on August 29. Some of the pieces relate directly the hurricane and its disastrous aftermath; others are targeted at the legacy of Fred Radtke, an infamous N.O. anti-graffiti crusader known as the "Gray Ghost" for his practice of painting over graffiti in gray paint—regardless of the color of the underlying wall. They're all pretty great. Five [UPDATE: Now six!] pieces, after the jump:

Several months ago, Brad Pitt fired his flack. His other half, Angelina Jolie, doesn't have a dedicated, full time PR rep herself either. The fact that the couple generally gets great press anyhow raises the obvious question: if Brangelina doesn't need a publicist, who does? The nuanced answer has to do with the changing nature of the celebrity media and the shifting balance of power among various types of Hollywood insiders. The blunt answer is, "Very few Hollywood people need flacks any more." Disintermediation is the new black! When you think of celebrity media today, think of two words: OK! magazine. Its entire business model is based on working *with* celebrities to come up with the nicest, most agreeable presentation possible. OK! is so celebrity-friendly it is edited by a former celebrity flack.

Are you familiar with the phenomenon that is Jared Seligman, wunderkind realtor to the downtown stars? If not, wake up and smell the $40 million in billings! Seligman sold that much property for the Corcoran Group last year at the tender age of 21, to real estate connoisseurs like the Olsen twins. And though he's already been profiled by W magazine and is a running meme at Curbed, He doesn't "really have time to pay attention to the press." The hectic life of a now-drinking-age condo king! Seligman started in the real estate game at 18, and he's already a millionaire. Cool kids love him!

There was a time in New York City's history, back in the heady days of "a few years ago," when nightlife queen Amy Sacco's life was a worthy item of gossip. She was at the center of an entire universe of celebrities at their most glittering. Today, she's worth chronicling mostly as the living embodiment of the transience of nightlife fame. And a new profile of her in Page Six Magazine (by former Gawker-er Joshua David Stein) can be seen as a grand requiem for Sacco and her Bungalow 8-driven empire. Nothing lasts forever... Sacco's rise to fame is familiar by now. She's just a Jersey girl who came to New York City, worked in the restaurant business, and made some important friends who eventually bankrolled her first club, Lot 61. She hit her peak with the opening of Bungalow 8 in 2001, which succeeded in turning the once-barren area of West Chelsea into the club capital of New York-to the point of destroying the exclusivity and isolation of the neighborhood that helped attract the top models and A-list celebrities to Sacco's clubs in the first place. But Sacco's more recent history is one of unmistakable decline. She opened a Bungalow 8 in London, which received (and still receives) a tepid reception from the locals. Bette, the restaurant Sacco opened as a "neighborhood joint" near her own Chelsea apartment, closed without warning earlier this summer. She got a slew of nightlife and image consulting jobs that, while lucrative, aren't nearly as glamorous as her former life as an NYC tastemaker. And she says she's simply getting tired of it all:

This morning we learned that Microsoft had selected the $10 million spokesman to revive its uncool brand: Vintage Mac aficionado Jerry Seinfeld. The collective response could be summed up as, "Really, him?" But Seinfeld may be just be one small part of the Microsoft coolness project! Fishbowl LA is reporting that the company's ad wizard and diet book author Alex Bogusky is considering lots of other celebrities for the campaign to help convince you that Vista is a smart buy. The (real) list of those purportedly under consideration: Vagina-touting comedian Sarah Silverman!