- Mike Shields, Mediaweek

It’s questionable whether Procter & Gamble intended for preroll ads for its Tide, Cover Girl and Herbal Essences brands to run just prior to a recent video clip showing Playboy playmate Kendra Wilkinson flashing a breast at onlookers on TMZ.com.

It also is highly doubtful that both HSBC and American Express deliberately ran banner ads within clicking distance of nude photos of High School Musical star Vanessa Hudgens on the snarky celebrity-gossip blog What Would Tyler Durden Do? (WWTDD.com).

Yet, as celebrity slip-ups continue to serve as fodder for a slew of gossip sites and blogs, more mainstream brands are finding their way onto these sites, despite their often-racy content.

In recent weeks, ads for Days Inn and Samsung have popped up on the blog Egotastic!, known for its photos of underwear-shedding pop stars. Aside from ads for P&G brands, AOL’s considerably more PG-13 TMZ.com has sported banners from Wal-Mart and Verizon. Last Thursday, WWTDD, which revels in disparaging celebrities, carried promotional ads for NBC’s 30 Rock.

The big question is whether content of this variety is simply becoming more acceptable for marketers given its popularity, or whether negligent ad networks are placing messages on sites many brands would rather avoid. Both could be the case, said several media executives.

Digital buyers report that across several categories -- particularly movie studios and products that target younger consumers -- brands have come to terms with whatever reservations they might have once had about the content of such sites, as they simply cannot ignore the passionate following the sites have built.

“Overall, I see them as being very viable because the eyeballs have moved there and they are very powerful,” said David Goodrich, senior vp, West Coast digital director at Universal McCann. “These sites know how to border the gray area and not turn into full-fledged porn sites.”

Added Goodrich, “If I am Axe, yes. If I’m Johnson’s baby [products], I’d be hard-pressed. But if you are launching Superbad, you want to be in Perez.” He refers to Perez Hilton, the outrageous, celebrity-mocking/adoring blogger often credited with inventing the genre.  Henry Copeland, founder and CEO of BlogAds, which sells inventory on PerezHilton.com, said that because the site restricts profanity and nudity to certain sections, it has landed business from Chili’s, Samsung, even Microsoft. “You’re definitely seeing an evolution in attitudes,” he said. “Our whole society is becoming edgier.”

But some evidence suggests attitudes may be shifting. Nielsen Online reports that unique users for both PerezHilton.com and TMZ are down -- by 22 and 11 percent, respectively, versus last year. Meanwhile, Yahoo!’s omg!, launched in June of last year, has roared past both those sites to take the lead in the entertainment category, attracting 13.3 million monthly unique users, nearly 4 million more than TMZ. The site credits its success to avoiding the nastier side of gossip.

“There are things we won’t do and won’t say,” said Yahoo! Entertainment general manager Sibyl Goldman, who heads omg!. “You won’t ever see starlets without their underpants. You won’t see us dig up legal documents. You can have fun and not be mean.” Goldman credits that approach with helping the site attract accounts including Nivea and Warner Bros.

While advertisers appear drawn to omg!’s softer touch, many predict brands will continue to open up to edgier celeb blogs, as long as they remain popular. “You go where pop culture is going,” said Jordan Bitterman, svp, media director at Digitas.

That said, Bitterman pointed to an emerging factor that could make marketers think twice about frivolous content: the economic crisis. “In this current economy,” he said, “you have to be completely mindful of what’s going on with people.”