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terry Cronin readily admits with a chuckle that, “Like every other [creative] in advertising, I’m trying to write a screenplay.” But unlike most, Cronin, a 46-year-old former Wieden + Kennedy creative director who has written spots for Nike and ESPN, no longer keeps his screenplay ideas hidden in his desk at BrightHouseLive in Atlanta. Instead, the executive creative director has been sharpening his storytelling skills in an increasingly popular medium: advertainment. The term describes advertising projects that don’t fit the standard constraints of television media buys but rather stretch beyond 30-second boundaries and strive to tell a brand story that’s more subtle and, the creators and sponsors hope, more entertaining.

Late last month, ESPN began airing the first 90-second chapter of The Scout, a six-minute film created by BrightHouseLive, a unit of Atlanta-based consultancy BrightHouse. Viewers of SportsCenter are told that the film, about a baseball scout past his prime (played by character actor Seymour Cassell) who discovers his next star, is presented by Craftsman at Sears. It’s the first installment in the ESPN Shorts initiative, which will integrate brands into shorts.

Whether airing shorts on TV programming, distributing their films via promotions and direct marketing, as DKNY does, or creating online films like American Express’ Seinfeld-starring “Webisodes,” advertisers are becoming increasingly interested in producing entertainment content to showcase their brands.

For Touré Claiborne, director of brand management and partnership marketing at Sears, investing in ESPN Shorts was a natural way to extend Sears’ message using a pop-culture vehicle rather than advertising. “Entertainment marketing for Sears—not just Craftsman—will become an increasingly considered area,” he says. “We believe that popular culture will help define the consumers’ perception about a brand, and TV and film are the areas in which to do it.”

While entertainment projects like The Scout need to stay consistent with Sears’ advertising, “ESPN Shorts is part of content,” says Claiborne. “Because it’s part of content, we’re part of the exciting programming known as SportsCenter. We’re embedded in the content.”

The advantages for ESPN is that the Shorts program offers clients a chance “to break through, to be seen uniquely,” explains Ed Erhardt, president of customer marketing and sales at ESPN ABC Sports in New York. “We see ESPN Shorts as a production house, the same way you would have a film house that produces communications that it can bring to advertisers and marketers. It will create six-minute films which incorporate an advertiser’s product or brand into the story line. That product or service advances or enhances the story line.” In addition to Sears, the film series will include beer, automotive and credit card initiatives, says Erhardt.

Finding just the right balance between storytelling and selling is especially important in projects packaged as entertainment. In the case of The Scout, the budding talent discovered by Cassell’s character is a 12-year-old boy who mows the grounds of a baseball stadium with a Craftsman lawn mower. “It’s a new way of thinking,” says Cronin. “You can tell more of a story, integrate a product much more naturally than having your character holding it or caressing it while smiling into the camera.”

Later this month, ESPN Shorts will debut a second six-minute baseball story, The Squeeze Play, produced by Ground Zero in Los Angeles for Miller Brewing Co. The film features a Boston family faced with an uncle’s death shortly before the final game of the World Series, a game in which the Boston Red Sox are competing for the championship.

DKNY has followed up last year’s New York Stories short film with Road Stories, a 12-minute tale that follows an actress driving cross-country to pursue her career. Material for the film, produced by Laird + Partners in New York, came directly from the designer’s latest collection, says Anjali Lewis, svp of global marketing and communications at Donna Karen International in New York. “The road trip carried through from the design room to the in-store communication.”

In fact, the production for the film, airing in stores and distributed through DVDs to DKNY customers, served a dual purpose. Shot in high-definition digital, outtakes from the film, directed by fashion photographer Steven Sebring, were used for the spring print campaign. In print, it’s impossible to track the whole story without using a costly multi-page ad buy, notes Lewis. “When you’ve got a single, you only see a little fragment of the story, and you’re expecting the customer to run with your idea. ‘Road Stories’ brings the story to life.”

The retail brand is also featured in the eight-minute film Friday Night Fever, co-produced by DKNY and Details. The short, directed by Tjebbo Penning, is the story of an immigrant worker whose life is changed by a white suit he brings to the cleaners for his boss. Film Movement, an independent-film DVD-subscription service, is distributing the movie, as well as a 17-minute Visa-sponsored short, Ecology of Love, starring Pharrell Williams of the band N.E.R.D. and the music-producing duo The Neptunes.

Earlier this month, Toyota’s Scion model was the star of a 22-minute film screened at the Tribeca Film Festival in New York titled On the D.L. The docudrama follows two friends, thirtysomething musicians Ahmir Thompson (a.k.a. ?uestlove of the Roots) and D.J. King Britt (formerly of Digable Planets), as they get their first driver’s licenses in their native Philadelphia.

“Scion’s DNA is to work with emerging, under-the-radar talent,” says Patrick Courrielche, managing director for Inform Ventures, Scion’s Los Angeles-based public relations and promotions agency. “One thing we didn’t want was this to be a heavy-handed commercial. They drive around in the car, make mistakes, laugh at themselves.”

The film, by music video director Andrew Guro, is featured in shorter clips on Scion’s Web site and on peer-to-peer sites such as Kaaza. The film has also generated some interest from music-themed cable stations, says Courrielche. Though the target market is 18- to 34-year-olds, “we’re going for a psychographic, not a demographic: independent-minded, intelligent people who are into the creative community and the arts,” he says. “For us, it was about getting the car in a lifestyle situation.”

American Express, a sponsor of the Tribeca Film Festival, made its own online-film debut in late March when it posted “Webisodes,” starring Jerry Seinfeld and Superman, that were created by Ogilvy & Mather in New York. Promoted in the New York market with three 15-second teaser commercials and an appearance on Today featuring the comedian and an animated caped crusader, the five-minute shorts feature the pair making classic Seinfeld small talk. In the first, directed by Barry Levinson (Diner, Rain Man), Superman rescues Seinfeld’s stolen DVD player. In another, the two get stranded in Death Valley.

“It’s its own category of branded entertainment—it’s more than a commercial and less than a film,” says David Apicella, senior partner and co-creative head at Ogilvy & Mather, New York, of the online-entertainment trend. “I think you’ll see more from more types of advertisers. We’re still in the beginning of it.”

The birth of the trend is widely credited to what is still considered the gold standard in advertainment, BMW Films’ 2001 and 2002 online series, The Hire, directed by Hollywood talent including Ang Lee and Tony Scott and featuring BMW as the star. Bruce Bildsten, creative director at Fallon in Minneapolis, observes that the creative team had the advantage of seeing the product in great movie chase scenes such as those in Ronin (directed by John Frankenheimer, another Hire director). “It was easy to make it another actor in the film. With other products, it’s a little bit more difficult.”

Which products best lend themselves to long-format executions is still to be determined, but Christopher Gebhardt, a former Ogilvy & Mather executive who is co-head of brand ventures at talent management shop The Firm, says it’s in marketers’ interest to make the investment. “There is increasing brand interest in funding films and increasing interest in the film community in making that happen,” he says. “For the cost of a couple of 30- second spots, you can have a whole piece of content that could be the next My Big Fat Greek Wedding or Blair Witch. If I’m a brand, I should be thinking about that.”

Whether it’s a 30-second commercial, a three-minute short or a three-hour film for a brand that’s distributed on TV, in theaters, online, in store or on DVDs, “it’s still advertising,” says BrightHouseLive’s Cronin. And ad experts note that the same rules apply: Give consumers something they love, and they may love you back.

“The thing that is important is creating communication that is getting into people’s lives. Whether it’s traditional or nontraditional marketing, it’s advertising, and if people don’t want it in their lives, they are now empowered to do [something about it],” says Ty Montague, co-creative director at Wieden + Kennedy in New York, who produced The Sweet Science: A Jordan Love Story. That 60-minute documentary for Nike’s Brand Jordan about boxer Roy Jones Jr. ran as programming on ESPN2 last December.

“The goal is to create something that comes authentically from the brand,” Montague says, “and do it in a way that honors both the audience and the distributor.”

Eleftheria Parpis is creative editor of Adweek.