Steve Lippia sounds a lot like Frank Sinatra – eerily so – but he’s no lounge-act impersonator. Not only does his repertoire includes a lot more than the Chairman of the Board – he sings  standards by Tony Bennett, Ella Fitzgerald, Bobby Darin and more – but he’s also made an art of interpreting Sinatra’s music. 

"People sometimes forget – they think of it as just being Sinatra," he told OnMilwaukee.com. "But obviously you have somebody who wrote the lyrics and wrote the melody and who built an arrangement around that. And they’re almost inseparable from (Sinatra’s) persona." 

Lippia will be bringing his "Simply Sinatra" show to Milwaukee on Tuesday at 7:30 as part of the Live @ Peck Pavilion summer series. 

He chatted with OnMilwaukee.com about Sinatra, his start in music, his favorite songs – and why he owes his career to Bing Crosby.

OnMilwaukee.com: How do you so closely replicate the Sinatra sound?

Steve Lippia: "With a 10-piece band, which is what we’re bringing to Milwaukee, it’s a little different size than what Sinatra recorded with. So we have to make some adjustments but it works great. He was such a great interpreter of his music, but he needed to have really great music to interpret and have really great arrangements to put together the ultimate package.

"A lot of times it’s not just his voice but those versions of his songs by those specific arrangers that you long to hear. My musical director Steve Sigmund will be conducting; he was with Ray Charles for 17 years. We’re fortunate to have Michael Arens on the bandstand playing drums – he’s a big force in the percussion and drum realm not just in Wisconsin but around the country."

OMC: How did you go from being a part-time roadie and businessman to having a successful singing career?

SL: "I was a roadie for Bobby Kay and his orchestra in Hartford, Conn., where I’m from. My night started at about six o’ clock and I’d get back home at around three in the morning and for that I got 15 bucks, and I thought it was just the greatest thing. When I started I didn’t know an alto saxophone from a baritone saxophone. Just by osmosis and being around it enough, you keep your eyes open and you’re half awake, you start to absorb this stuff. Little by little Bobby started working me in and I became the featured singer with him. But I was going to college and grad school, starting out life – it was a serious side thing for me. 

"By 1998 I had moved to Florida, I hadn’t sung in five or six years. I had started my own independent contracting business, I had studied law for a while, been a stockbroker in Boston and New York. And I just got the bug again. I started singing in a local band. One thing led to another and pretty soon a tape of mine got into the hands of some big people in Beverly Hills and in Las Vegas, and within a year they decided they wanted to manage my career. They got me a headlining engagement in Las Vegas in a show that was built for me with a 21-piece orchestra. The person who was the head of that was my music director Vinny Falcone Jr., who conducted for Paul Anka and Frank Sinatra."

OMC: What's your favorite Sinatra song?

SL: "It’s really hard to bring it down to one song. There’s thousands to choose from. I perform "Send in the Clowns" a lot. It’s such a powerful song. The depth of those lyrics…it’s just so profound. When do they bring the clowns into the circus? When something goes awry. That’s what the song’s about. You’ve got these lyrics that are a little bit obtuse, a little hard to figure out – "Isn’t it rich/ Aren’t we a pair/ Me here at last on the ground / You in mid-air" – a lot of metaphorical references that can at times be a little obscure at best. But if you really start to inhabit them and listen to them you realize that this guy has this great relationship, he doesn’t quite know that, doesn’t quite get it. It’s early in his life, he’s still going to go out and slay dragons, you know? How can two people who are so much in love fail? Because it’s a matter of tragic timing. So send in the clowns. Something has gone extremely, extremely wrong."

OMC: How did the music of Frank Sinatra change the industry?

SL: "I’ll say this – if there was no Bing Crosby, they may never have been a Frank Sinatra. Bing Crosby – he was such an important and significant figure and all these years later he’s never really gotten that due. He didn’t have that snap, that hipster thing that Sinatra had. But Big Crosby was a force. An older friend of mine had told me once what Big Crosby brought to music was 'talk-singing.' Before that people sang like quasi-classical or really corny stuff, it was really weird stuff, or kind of folk music passed down from generation to generation. Bing Crosby was the first guy who created this entire style of music and it was only because of him that Sinatra even knew that was possible."

OMC: What would you say to Frank Sinatra, if you had the chance?

SL: "I wouldn’t want to say too much. I’d want to listen mostly. He had a very intense life, he packed several lives into the life of one man – I mean, he recorded 1,500 songs. Who in the world has time to record 1,500 songs?

"My music director Vincent Falcone, Jr. was Sinatra’s conductor for years. He’s said more than once time to me – a lot of people who worked with Sinatra later in life refer to him lovingly as the ‘old man’ – he said: ‘The Old Man would’ve really loved you. He would’ve been behind you, been really supportive.’ Vinny’s kind of the bridge between the man and my own efforts in the music world. So that’s always given me a certain amount of pleasure and hope."