Sophie Milman’s immigrant experience has shaped not just her personality but also her approach to music.

Take for instance the Meredith Wilson song Till There Was You, the fifth song on the jazz singer’s newly released fourth CD, In The Moonlight.

“That song takes me back to a time that was very difficult for us – it was the best of times and the worst of times,” the 28-year-old Juno Award winner says.

Milman, then seven, had just moved with her parents to Israel from Russia. Her parents had to work several jobs to make ends meet, and Milman had to grow up fast, sometimes only seeing them on Shabbat.

“Music was how we communicated.  [Till There Was You, the Beatles 1963 version] was the first English song I learned to sing. I was a big Beatles fan. We had a car and on a long trip — which in Israel means anything longer than 20 minutes — I was the stereo. My dad would always request that song. I would sing Beatles songs, Queen songs and Deep Purple songs.”

Now, two decades later, she finally got to record it. “It’s a simple song, a ditty, it’s not very sophisticated… but there’s something so beautiful about it.”

Then, nine years after moving to Israel, her family uprooted again — this time moving to Canada. “There’s nothing like picking up and starting over from scratch — twice,” Milman says.

“My experience was very different,” she says. “Leaving everything you know and never going back. I’ve met many rich Russian Jews who come here to go to school and go back over the summer. It was nothing like that for me. We had no money. On my birthday I would receive a telegram from my grandparents in Russia because we couldn’t afford a phone call!”

This summer, Milman had a chance to go on what she called a “reverse journey,” going back from Canada to Israel and Russia.

Russia was just a visiting trip, but in Israel she got the opportunity to perform for the first time. She did three concerts – the first was an emotional show at the Zappa Club in Herzliya.

“I’ve played Massey Hall in Toronto and the Hollywood Bowl [in Los Angeles] but the show at the Zappa Club was one of the best shows of my life. Even my husband, who’s seen me 100 times, says it was the best show I’ve ever done. It was something very special.”

Milman was nervous before going on stage. This was the first time her relatives in Israel as well as her old friends would be seeing her. Although she purposely had the venue darkened, she still knew they were there.

Milman, admittedly, gets emotional even at the best of times and says that no matter how long you’ve been singing, you never quite get used to it.

“Singing is the only profession in the world where you go out and all eyes are on you,” she says. “You have to connect with people in a way nobody else needs to.”

In The Moonlight is a strong, sophisticated recording, one that shows a more introspective and mature Milman.

It features 13 songs, from the flirtatious George Gershwin/Buddy DeSylva opener Do It Again to the hauntingly seductive Serge Gainsbourg song Ces Petits Riens and the Duke Ellington classics Prelude to a Kiss and Day Dream.

“This album’s moodier, lusher and more romantic,” she says.

“I think that without my previous records I couldn’t make this one. It’s all a natural evolution. I am extremely proud of [2009’s] Take Love Easy, and this album reflects a lot of growth.”

Milman recorded In The Moonlight in New York with Grammy-nominated producer Matt Pierson.

“I was really looking forward to it and yet I was terrified,” Milman admits. At first, she was reluctant to leave her comfort zone. “But I felt like I needed to do it.”

Working with top players such as pianists Gerald Clayton and Kevin Hays and guitarists Julian Lage and Romero Lubambo helped her up the ante. “When you’re in a recording studio with [such musicians] you have to sing the best you can. It allows you to push yourself in a way you normally wouldn’t.”

Also for the first time, Milman enhances her music with orchestral strings on several songs.

“There’s more personal maturity, and the strings really add to the sound. The overall effect is a more grown-up Sophie Milman record. It’s a better, sleeker version of what I’ve been doing.”

Milman’s second CD Make Someone Happy won a Juno Award in 2008. She admitted to having high hopes for this record but conceded, “I’m not greedy. One win is enough.”

As on her previous recordings, she also throws in a contemporary tune, this time Feist’s regretful So Sorry.

“People suggested that one to me. I don’t often accept suggestions, but that Feist tune is perfect for me. I’m a very temperamental person, and when I fight, I’m very fierce. There’s also that whole Jewish guilt thing as well.”

Although she’s not particularly religious, Milman feels very connected to Judaism — at least on a cultural, traditional level.

As is the case for many Soviet Jews, it was hard for her family to be observant in Russia. In fact, it wasn’t until they came to Canada in 1999 that she first went to a shul. But just like her music, Milman is constantly maturing and evolving on a personal level. She got to host her first Rosh Hashanah dinner this year.

“My husband [lawyer Casey Chisick, whom she married two years ago], who’s way more religious than I am, roped me into it. I did the whole thing, two briskets and chicken soup made from scratch. I’m a real balabuste!”

To her husband’s chagrin, marriage is not slowing Milman’s touring schedule. She just returned from Japan and immediately launched a mini-Canadian tour that took her to Ottawa, Quebec and Montreal. She’ll be spending most of the rest of the year touring the United States. She’s scheduled to perform in Markham, Ont., on Jan. 27, 2012, and at Massey Hall in Toronto on June 1, 2012.

For more information on Sophie Milman and In The Moonlight, visit www.sophiemilman.com.