By Jennifer K Mahal

Listen to James Naughton croon and you know. This cat's cool. So cool the 56-year-old's hip. So hip, he's able to have fun with it in his cabaret show, "Street of Dreams," which plays Thursday through Jan. 27 at the Orange County Performing Arts Center.

Among the songs Naughton will perform is the Dave Frishberg-Bob Dorough sendup "I'm Hip," in which a wannabe cool guy shows just how out of it he is.

"He's one of these guys trying to be such a sophisticated musical hipster, but he's obviously a jerk," Naughton said on the phone from his Connecticut home. The same cannot be said of Naughton. The two-time Tony Award winner -- once for "City of Angels" and once for "Chicago" -- has been called the "master of hip" and the "epitome of cool" in reviews.

"It beats being called untalented or stiff," Naughton said. "Being cool is basically every kid's motivation from the time we're about 9. 'Yeah man, he's cool."'

You get the feeling Naughton has been ice in a nice way for a while. He grew up on the sounds of Billy Eckstein and Johnny Hartman. There are no show tunes in his act, which features the musical direction of John Oddo.

"I'm not a show tune kind of guy," Naughton said. "There's this other kind of body of music that I've always kind of gravitated toward."

The composers in the show include Duke Ellington, Hoagie Carmichael and Randy Newman.

"It's an eclectic bunch of music," he said. "Most shows build around a composer or genre. It makes for a homogenized kind of show, and this is more varied than that."

Naughton is primarily known as an actor who sings. The graduate of Brown University and Yale School of Drama made his 1971 New York debut in "Long Day's Journey into Night" with Geraldine Fitzgerald and Robert Ryan. Most of his work has been on the stages of New York and Connecticut, where he has often performed and directed for the Williamstown Theater Festival. A festival production of Arthur Miller's "The Price," which he directed, moved to Broadway in 1999.

But his singing roots go way back. As a kindergartner or first-grader, he sang "I've Been Working on the Railroad" with two other guys, all dressed in dungarees with patches and carrying shovels.

By late elementary school, the man known to television audiences as the father of the title character on "Ally McBeal" had graduated to Elvis.

"I remember in fifth or sixth grade singing 'Love Me Tender' at another one of those kinds of talent show nights," Naughton said. "The principal made a big deal out of having me not wear my collar up because he was concerned it projected a hoodie image."

By high school, Naughton played three sports -- baseball, soccer and basketball -- and was appearing as the lead in musicals such as "Carousel" and "Annie Get Your Gun."

"I recently came upon a picture in a carton in the attic, I was 15 or 16 and playing Emile de Becque [the lead in "South Pacific"]," Naughton said. "Talk about silly. I was this little baby-faced boy with goo in my hair. Someone stuck some clown white in my hair, and that was Emile de Becque."

It's a little surprising to discover that Naughton has only done three Broadway musicals in his career -- one a decade, starting in the '70s with the Cy Coleman show "I Love My Wife." Coleman also wrote the music for "City of Angels."

"I think I rather consciously tried to avoid singing because I thought that if I did musical comedy, there'd be no chance to be able to do straight plays," he said.

Though he toyed around with doing a cabaret show for about 25 years, it wasn't until he performed in a Coleman tribute about four years ago that it started to come together.

It was there he met jazz artist George Shearing, who was impressed with Naughton's performance.

"He said 'I'd like to play for you.' And I gulped and stuttered and hemmed and hawed," Naughton said.

They exchanged numbers and later met.

"He sat down at the piano and said, 'This would be a good song for you, Jim,"' said the husband and father of two.

Among the songs Shearing suggested was "The Folks Who Live on the Hill," a Jerome Kern and Oscar Hammerstein tune that is in the show.

Shearing returned to England, and a few weeks later Naughton received a tape.

"It was 90 minutes of George Shearing playing and singing songs for me to sing," Naughton said. "At that point I thought, 'I've been talking about this for a long time. If George Shearing went through the trouble of making a tape . . ."'

A little help from friends Rob Fisher, music director of "Encores!," and cabaret star Mary Cleere Haran matched Naughton with Oddo, who is best known for his work with Rosemary Clooney.

The rest is a lot of work and show biz history. His first solo show, "James Naughton Live," premiered at the Manhattan Theater Club in June 1998. "Street of Dreams," presented by Mike Nichols, appeared at the Promenade Theatre in early 1999 to great reviews. Naughton has plans to record an album of the tunes and may even do the show on cable.

His future also holds directing a new production of Thornton Wilder's "Our Town," starring Paul Newman as the stage manager.

Which doesn't mean there won't be more music in his life. He's learning a group of Rodgers and Hart songs and listening to a lot of Sammy Cahn.

"I have this kind of jones for singing music," he said.