As BRANDON, A 15-YEAR-OLD high school sophomore, leaves school, he text-messages his friend Gabe, who just bought the new Madden for Xbox, that he’s heading home for a little online tournament. Then Brandon fires up his favorite MP3, “In Da Club” by 50 Cent, and he’s on his way.

Brandon is a busy kid, with a lot of interests. When he’s not in school, he’s in front of some sort of screen: computer, videogame, cell phone. He’s listening to music or researching the latest gadget he’s saving his money for. He’s playing videogames at a friend’s house or hanging out at the mall. He’s a moving target and, like most teens, he has been marketed to since the day he was born. He knows what advertising looks like. He knows what it smells like. He’s seen it all before.

This is a fickle, seemingly sophisticated, fast-moving bunch, but marketers are undeterred. They can’t ignore Brandon and his peers, who are expected to spend a significant $175 billion on themselves this year, a 3 percent increase over last year, according to Teenage Research Unlimited, Chicago.

And their disposable income keeps growing, says New York-based Youth Intelligence. A recent study found that 43 percent of males and 44 percent of females ages 14 to 18 spent more in the past six months than they did during the previous six months. A study conducted in June reports that males say they spend $71 in a week; female spend $61.50. “They are a recession-proof demographic. They’re still getting allowance, mowing lawns and babysitting,” says Cynthia Engelke, manager of research and trends for Youth Intelligence.

The issue for advertisers is how to shake those dollars loose. The problem often lies in the fact that marketers aren’t that adept at the technologies teens use in their daily lives. SMS (short message service), photo-enabled phones, Instant Messenger and even certain aspects of the Internet are beyond some marketers. And just how many hours have the people making the marketing decisions logged playing Grand Theft Auto?

“Teens are the most active target in the world,” says Jarrod Moses, CEO and president of Alliance, an entertainment and strategic partnership, which is part of the New York-based Grey Worldwide. “If you think you’ll reach them by just throwing an ad on the WB, you’ll be wrong. You can’t look at TV as a primary vehicle. You have to build a lifestyle campaign. The traditional way of advertising and marketing does not exist anymore.”

Among teens 13 to 18, 82 percent have computers, 62 percent have videogame consoles, 49 percent have cell phones, 32 percent have SMS and 13 percent have PDAs, according to Born to Be Wired, a new study commissioned by Yahoo! with Carat Interactive. “Growing up with the Internet, cell phones and other new information receptacles, teens today are multitaskers, able to easily assimilate multiple marketing communications simultaneously,” says Richard Leonard, vp of New York’s Zandl Group.

Realizing this, Coca-Cola, a company whose attempts to attract younger consumers have sometimes yielded less-then-stellar results, has tweaked its new fall under-the-cap promotion. The Cokemusic.com campaign has teens looking under the caps of specially marked bottles for a secret code. That code can be then be keyed into the Web site for points (called Decibels) redeemable for prizes. For the first time, consumers can send a text message via SMS-enabled cell phones to Coke (653 is the short code) to have the points automatically entered into their accounts.

“The barrier we noticed, despite the success of our fall and summer programs, was that someone has to hang onto the cap and wait until they can get to a computer and enter the code,” says Doung Rollins, associate brand manager for Coca-Cola. “Cell phones are an important accessory to teens, it’s important o innovate against this [technology]…It will be a learning experience [for us].”

Coke has the right idea, says Shawn Parr, CEO of Bulldog Drummond, San Diego. “Technology is like a knife and a fork to them. They adapt technology into their everyday routines. They are not enamored with it like the generation before.”

The companies that understand this are better able to put together seamless campaigns aimed at teens. For example, New Line Cinema will be the first to run 15-and-30-second streaming-video ads on AOL Instant Messenger for its upcoming movie Elf, starring Saturday Night Live alumnus Will Ferrell. On Nov. 7, regular users will see the ads running in the space atop the buddy list. New Line found earlier success running static banner ads for its hit horror movie Texas Chainsaw Massacre.

It almost goes without saying that the Internet is a vital part of the teen marketing mix. Music television network Fuse, renamed last May from MuchMusic, created the Interactive Music Exchange (interactivemusicexchange.com) as one way to get teens intimately involved with the artists that appear in its music videos. The online program has teens buy and sell hot artists on a virtual stock exchange to win prizes. “It’s a program that young adults can feel ownership over,” says Mary Corigliano, vp of marketing for the channel. “Teens don’t have a credit card for an Xbox. If they are good at IMX, they can win one. Teens want free stuff.”

Then again, music is an easy draw. One thing teens today share with teens of the past is the fact that they are influenced by their favorite artist. But forget about songs that talk about the hot boy or girl at the next locker. Hip-hop is a veritable laundry list of hot products. There have been 1,050 references of about 66 different brands in songs ranked in the top 20 through the beginning of October, according to San Francisco-based brand consultancy LucJam. Burger King had 16 mentions while Payless ShoeSource had 25 and Nike had 21.

“Hip-hop is incredibly materialistic, making it a good place to talk about materialistic things,” says Lucian James, president of LucJam. “It’s about breaking news, culture, and the here and now. [And] it serves the eternal purpose of annoying parents.”

Jameel Spencer, president of Blue Flame Marketing and Advertising and chief marketing officer of Bad Boy Worldwide, New York, says, “Hip-hop represents everything kids are into. It’s cutting-edge, against the grain. It comes from [the] underclass and is highly aspirational. It can catapult a brand from obscurity to the mainstream in a minute’s time, but it can make [it] go away just as quickly.”

Tying in with hip-hop is a tricky business, for both brands and artists. Artists aren’t likely to rhyme about brands for cash — they would be viewed as sellouts. And old-school companies are fearful of forming partnerships due to sometimes-explicit lyrics. Pepsi, for example, ran into some trouble earlier this year: it had to pull ads featuring Ludacris because of objections to his profane lyrics.

A less-controversial venue that is receiving more attention is videogames. In-game advertising is not a new phenomenon, but it is becoming more accepted among advertisers. New Electronic Arts title SSX 3 has in-game product placement for the new 7 Up soda, dnL; Need For Speed Underground features McDonald’s; and James Bond 007 Everything or Nothing features Porsche and Aston Martin.

“It’s more about product interaction than product advertising,” says Chip Lange, vp, marketing for Redwood City, Calif.-based EA. “You have to figure out a way to permeate the teen lifestyle without being gratuitous.” Lange says that as gaming moves online, ads will be able to be refreshed and altered within the games.

Buddying up with hot videogame properties in the real world has its advantages, as well. Microsoft Xbox and Mountain Dew combined to create “the Dew Den” at the Mall of America this past summer. The lounge allowed gamers to try the latest Xbox games and compete in Xbox Live tournaments for a chance to play on—air against a TV host from the cable channel G4, which is dedicated to videogames. The Dew Den was integrated into a national show that ran on the cable channel. “Like any good pop icon, you have to keep reinventing the brand,” says Angelique Bellmer, brand director for Mountain Dew. “Gaming as a lifestyle is so relevant. It is about the same thing Dew is: pushing the limits, being over-the-top, irreverence.”

Bellmer says the brand, which is a teen staple, never takes a step without talking to its target market first. “They own it. They define it. They tell us what’s cool. I feel like I’ve talked to every other teenager in America because of the amount of research we do,” she says. Mountain Dew, which has the full backing of parent PepsiCo’s marketing heft, spent more than $62 million on media in 2002, according to TNS Media Intelligence/CMR.

Out of necessity, smaller brands have taken a less obvious and far less expensive tack. Yoo-hoo, part of the Snapple Beverage Group, a division of Cadbury Schweppes, London, has a very small marketing budget relative to its competitors. Still, Yoo-hoo has managed to win teens over by hitting the alternative music festival Warped Tour since 1998 with free samples and off-the-wall contests. For example, teens can get free stuff if they chug the chocolate drink out of a boot. This is called a “shoe-hoo.” Last summer, a radio contestant dove into a Porta-Potty filled with its new Double Fudge flavor in order to win free concert tickets.

“A little brand like Yoo-hoo has to make a big noise,” says Kristin Krumpe, director of marketing for Yoo-hoo. “They have to get people scratching their heads like, ‘I can’t believe they’re doing that.’ Smaller brands are freer to take more risks. They are not as high-profile among stockholders or anyone else.”

Adds John Bello, who built up SoBe teas and juices to such a height that Pepsi bought the company: “You need to be where they are. You need to be relevant. You need to be authentic. You need to blend. You need to give out swag and brand the event beyond the product. That’s what sticks. Slick, polished, expensive does not work.”

There are still a good number of brands trying to reach teens through their TV sets. This is not all for naught, says the Zandl Group’s Leonard. “Good advertising is very effective in reaching teens,” he says. “It alerts them to new products and helps keep mature brands relevant and top-of-mind. Two out of three teens on our consumer panel have a favorite commercial, so they are definitely paying attention. With the exception of the small, subversive, indie crowd, most teens are not anti-advertising. They are just anti-bad-advertising — especially ads that appear to pander to them or try too hard to be cool.”

Attempting to read the tea leaves about trends to see what will be cool in the coming months “is what leads marketers to the biggest mistakes,” says Michael Wood, president of Teenage Research Unlimited. “They automatically assume they have to somehow associate themselves with cool. Then it ends up backfiring on them.”

Whether it’s Coca-Cola’s recent “Life Tastes Good” effort, which showed a handful of dorky surfers and kids leaving a concert on a miraculously empty train or any of a number of McDonald’s’ carousel of old creative, teens know what rings false. “until recently, Coke tried everything so blatantly to reach this target audience,” says Parr. “And McDonald’s seemed to change every six to nine months. They lack a degree of consistency and authenticity. A lot of companies have spent millions to create an image of who they are. To then try and speak to teens in a different way — it doesn’t work. Just be you. If you’re McDonald’s or Coke, just be McDonald’s or Coke.”

In fact, says the Born to Be Wired study the basic tenets of marketing still apply. For instance, rather than worry about how to get mentioned in the next Jay-Z song, marketers should make certain they put a quality product on the market. According to the study, 86 percent of respondents said the most important aspect of a brand is that it’s worth the money spent. And 83 percent said a company needs to make high-quality products. “There are brands you grow old with,” says Blue Flame’s Spencer. “People get on and off things quickly, but the brands that stay true to their core essence will stay around. Look at Timberland. They’re good for the cold and the snow, and they maintain a fashion sensibility. They don’t have to change their brand message.

“Once you go and change it and try and chase teens, you’re trying to hit a moving target,” continues Spencer. “No one does well with that.”

Dead last on Born to Be Wired’s list of what influences a purchase: whether a product is endorsed by a celebrity they like. Only 7 percent said it’s important. Case in point: does anyone remember the “Life Tastes Good” ad starring the Wallflowers’ Jakob Dylan? Neither do teens.

Kenneth Hein is a senior editor at Brandweek.