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Tony Bennett is steppin' out as an ad spokesman appealing to the unlikeliest of groups-Generation X.

The dapper 67-year-old crooner, known for such trademark hits as "I Left My Heart in San Francisco," "Fly Me to the Moon" and his recent Grammy-winning album and MTV video "Steppin' Out," has been riding a wave of popularity with twentysomethings that hasn't gone unnoticed by the ad industry.

Already, WordPerfect Corp. and Cluett Peabody Co.'s Arrow shirts have enlisted Mr. Bennett as a pitchman to capitalize on his cross-generational appeal.

And DDB Needham Worldwide, New York, is looking at Mr. Bennett as a potential endorser for an undisclosed client, a spokesman confirmed.

Lintas' newsletter on May 5 noted Mr. Bennett's popularity with the MTV set and his seemingly incongruous June 1 "Unplugged" special where he will sing old favorites with Elvis Costello, k.d. lang and the Lemonheads' Evan Dando.

"Like Sinatra and a handful of others, he's got a kind of coolness about him," said Alfred Schreiber, communications director at Lintas.

Software marketer WordPerfect hopes to drive traffic into computer retailers' showrooms with free tickets and complimentary backstage passes to Mr. Bennett's six-month, 40-city concert tour. The tour is being sponsored by WordPefect to promote its Main Street line.

P.S. Productions, Chicago, handles promotion and event marketing.

Arrow shirts this month breaks a spread in Business Week, Details, People, Rolling Stone and Sports Illustrated featuring the impeccably dressed singer. The ads allow Arrow to reach a younger generation without alienating its core consumers.

"He's a dapper, intelligent guy. Anyone with a fairly sophisticated image or product would find him an appealing spokesperson," said Barry Breede, group account director at Arrow agency Mandelbaum Mooney Ashley, San Francisco.

"Mr. Bennett's resurgence lately is just part of his timeless charm," said MTV Senior VP-Marketing Howard Handler. "He's one of the great singers and song interpreters. Also, he's a good sport and willing to laugh at himself."

Bradley Johnson contributed to this story.

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