Rachael Yamagata even comes with her own chamber orchestra. Now that’s what I call a class act. Surrounded by cello, violin, electric guitar, bass and drums, the effusive singer--songwriter from Arlington, Virginia, looks so right at home on stage.

“It might be the saddest song I’ve ever written,” she said, before playing her first song. “It’s not romantic, it’s not the first time, it isn’t magic, it isn’t soulful – it’ll do,” she sang, in ‘It’ll Do’, taking care to enjoy and enunciate each word as if she were savouring a tasty lemon drop.

She played the first verse solo and was then joined by the ensemble. You could hear the fragile progression crawling step-wise up the keys, like an escalating whisper in a thriller.

“I’m not a saviour/I’m not a saint/I’m not a muse to fill your soul/But I will do, for you,” she continued, on that same sanguine continuum. It had that Cole Porter feel, a great opening touch.

Yamagata sang for six years with Bumpus before creating a solo act in 2001 and producing four EPs and three studio albums. She’s been known as a wildly popular writer who gets her originals placed on daytime soaps, ‘ER’ and ‘Grey’s Anatomy’ and American coming-of-age and comedy films She has collaborated with singer-songwriter Rhett Miller and was inspired by classic artists like Carole King and James Taylor. Onstage she was quick to crack an aside or to slow the world down, inhaling the warm vibes of the cool room. After all, this place is an elegant winery.

She talked about coming back to Chicago, where she worked for a decade as a waitress and attended Northwestern University, with affection. “Chicago is my musical birthplace,” she exclaimed, looking pointedly at the faces in the first row and scanning the back. This comment is exactly what the fans in this beautiful room came to hear.

‘Heavyweight’ is from her latest EP and it was inspired by the ‘Rocky’ film series. The female violinist dressed in a striking red dress helped amplify tonight’s rendition.

Yamagata described ‘What If I Leave’ as her “relationship purgatory song,” and then picked up her guitar. “Do you want a happy song? Then you’re at the wrong show,” she offered, with a half-moon smile.

‘Elephants’ was one of her most evocative numbers. She started alone and then got increasing support by the band. Soon she was drenched in emotion, especially when she sang, “So for those of you falling in love, keep it kind.”

She eased back into a calypso with ‘Saturday Morning’, and was joined onstage by singer-songwriter Ed Romanoff. The song was very catchy and the ensemble was clearly having a great time, pulsing to the infectious beat and offbeat lyrics: “It’s a little love/It’s a little soul.”

“I know it’s over, but I stayed in it for at least two years,” she said, musing about one of her failed relationships. She had made several self-deprecating remarks about her love life up to this point and several somewhat caustic remarks about writing only sad songs. It became increasingly easy to identify with her.

But when a heckler boldly asked: “What’s your longest relationship?” you could hear a pin drop. Wasn’t that comment a little bit over the top? Ed Romanoff, for one, tried to make light of it. “Now we’re really getting somewhere,” he said, lifting his hands off his guitar and waiting for something to break the tension.

Rachael faced the audience. “Seven years.” She rolled with the punches and met her heckler straight on. Unphased. She hopped back on the horse as guitarist Ann Klein peppered up phrases on ‘Sunday Afternoon.’

Rachael faced the audience once more and confessed: “I lived in nine different apartments in ten years.” A number of local faces registered compassion. Romanoff joined in as she sang, soulfully, ‘Duet,’ which she had recorded on her album “Elephants…Teeth Sinking Into Heart,” with Ray Lamontagne.

‘Has It Happened Yet?’ and ‘Worn Me Down,’ put us under a spell as her pretty head voice drifted into a sea of low, feathery tones. You could hear traces of Fiona Apple and old time blues, and the dynamic ‘Dealbreaker’

The encores ‘Be Be Your Love,’ and ‘You Won’t Let Me’ were sealed with pizzicato and lots of passion. Rachael Yamagata seemed overjoyed about the effusive applause, blushing the shade of fine Bordeaux, (which flowed at a nearby table). Her lovely and long dark hair framing her flowing dress, she promised to “make more music” if we continued to listen. Now that’s a deal breaker.

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