‘Uh, Cadillac grills Cadillac mills. Check out the oil on my Cadillac spills’ goes a rap by Ludacris. Which is good news for Cadillac, a brand that is looking to reverse its image as ‘grandpa’s brand.’ It’s not the only one either. Other traditional brands like Old Spice, Arrow and Moores have been repositioned, or ‘youngified’ if you will, in an effort to grow market share.

But Cadillac is luckier than most; Ludacris and other rappers have helped make the brand cool again. And there’s a reason it happened, one that’s key to the success of any brand wanting to take its target younger: There’s an authenticity there, says Max Valiquette,

president at youth marketing consultancy Youthography, of Toronto.

Valiquette, who founded his agency almost six years ago and has worked with the likes of Budweiser, Hershey, and Ford of Canada, adds: ‘If Ludacris drops the name of Cadillac, that’s actually significant. [It’s because] Cadillac used to stand for something – freedom. It’s a little bit easier if you can tap into that authenticity, but it’s a double-edged sword. Young people don’t want to drive the same car as someone four times as old as they are.’ Brands fall into traps, he says, when they try to go ‘from zero to 60’ in seconds.

Certain brands do recognize this; instead of aiming too low, they are trying to decrease their target age by a decade or so. Nonetheless, that still has required a change in marketing tactics.

Take Arrow shirts. The 150-year old brand hasn’t advertised, in Canada at least, for about 10 years. And it’s always been known as the classic brand preferred by older men – picture stacks of white and blue and you’ll get the idea.

Toronto-based John Forsyth Company, which assumed the Canadian licence for Arrow in 2001, launched a stylish fall line that includes bold colours and contemporary patterns.

But, says Oliver Morante, EVP at John Forsyth, ‘the average customer, according to our market research, is 47 years old. Basically we’re trying to lower that to between 30 and 35.’

Morante says sales of Arrow shirts had been holding steady, thanks to its popularity among men in their 40s, 50s and 60s, but that the brand wasn’t growing. ‘If that happens you sooner or later lose market share and that’s what happened. Tommy Hilfiger and Ralph Lauren started to chew some of that market.’

Enter John St. to the rescue. The Toronto-based ad agency developed a campaign based on the theme ‘killer shirts.’ Killer, as in hip, get it? Advertising includes a TV spot, transit shelters and backlit billboards in Toronto and Montreal that portray a stylish guy deftly dodging arrows. Stephen Jurisic, co-CD at John St., says the brand has achieved a Banana Republic-type of look (albeit with wider distribution in department stores) so the tagline makes sense. ‘We looked at the product, and we looked at what icons they had, which was the arrow,’ he says. ‘The idea came from a bold client, wanting to stand out.’

John St. has also helped Moores Clothing for Men stand out a bit more among younger consumers. Or more accurately, the agency helped the retailer figure out that its customer was more youthful than it thought.

‘We did a focus group, and we realized it was a customer in his mid-thirties to mid-forties,’ says Moores’ Toronto-based president Dave Starrett. ‘The guy enjoys sports, has a couple of kids he is devoted to, and has a sense of humour. When we ran through all of this, the question became: ‘Are we really appealing to this customer?”

The retailer seemed not to think so. It retired its TV campaign depicting suits carefully

constructed in a factory setting and, while it kept the tagline ‘Well-dressed. Well-priced. Well-made,’ it debuted new advertising last spring with a much more comedic and

contemporary tone.

For instance, one of the commercials features a bloke bending down to pick up a set of keys only to hear a humiliating rip.

Moores also launched a tuxedo rental business in January, both for prom-bound teens, and grooms-to-be. Two TV spots addressed these audiences. In one, a bride awakens from a

terrible nightmare in which her fiancé shows up on the big day in a gaudy powder-blue tux, while the other has a teenage boy and girl getting glammed up for the prom.

Starrett says that so far tux rentals have exceeded targets by 60%. As for business in general, the shirt, suit and tie business is up by double digits on the year, with overall sales up 8%.

And what about Cadillac? Fred Lautenschlager, ad manager of the Chevrolet, Cadillac and Hummer brands at Oshawa, Ont.-based General Motors, says the brand’s emergence in hip hop culture wasn’t purely coincidental. ‘It started with the launch of the Escalade four years ago…. The strategy was to get the product in the hands of key influencers in the U.S. For instance the vehicle was given to basketball players. Cadillac always had a sense of equity, prestige, and elegance, but it didn’t have the cool, hip factor.’

Lautenschlager points out that the automaker has been working hard to rejuvenate Cadillac product. The most recent example is the STS, which focused on three key areas: quality, design and performance. Thus the vehicle emerged with an angled, stylized look and a more powerful engine.

‘The target is into the lower to mid-40s range, whereas traditionally it was much higher. But it’s not yet where we want it to be,’ says Lautenschlager, who adds that women are also higher on Cadillac’s radar.

As a result, recent advertising for the STS has strayed from the normal car ad scenarios in an attempt to appeal beyond ‘gramps.’ ‘STS envy’ from MacLaren McCann, for instance, is much more fun than most car campaigns. According to Chris Harrison, VP group CD at the Toronto-based agency, the entire effort was born from imagining what ‘problems’ one would have if one owned the ‘Cadillac of Cadillacs.’ Brainstorming led to ideas such as: ‘It’s so beautiful people would stare,’ and ‘You’ll love it so much, you won’t be able to walk away.’

This led to a mock self-help Web site, www.cadillacstsenvy.com and magazine ads – which ran in urban publications – advising ‘afflicted drivers’ to visit the URL. One neat idea MacLaren had was to place business reply cards, outlining the various ‘difficulties’ faced by Cadillac owners, between double-page spreads featuring beauty shots of the car.

Cadillac has also been sponsoring urban, artsy events, such as a Toronto International Film Festival party thrown by Jeanne Beker pub Fashion Quarterly and another bash organized by Inside Entertainment. The brand also

partnered up with The Toronto Arts Festival. At these events, reps handed out fob keys – containing flashy multimedia presentations on the STS – which could be plugged into

recipients’ computers.

‘We delivered information in a highly entertaining way,’ says Lautenschlager, who adds that the fob likely has a longer-lasting impact than print collateral. ‘We think the key to changing people’s opinion is to get them to experience each product.’

Cadillac also recently inked a sponsorship deal with Ron Fellows, a well-known NASCAR driver.

All this is not to say that Cadillac is

abandoning its older consumer altogether. In fact, as Lautenschlager points out, a 55-year-old no longer feels like a 55-year-old, so Cadillac’s stylish approach is a safe one. ‘[With ‘envy’] there was definitely a discussion of risk and ‘Can we have that level of fun with ourselves and our potential customers?” he says. ‘But while we still need to maintain our customers at the higher end, we’re trying to get away from that [old] imagery.’