Rachael Yamagata is the queen of crafting the most melancholy of heartbreak songs, the ones you immediately yearn for after a breakup or any time you long for a fallen lover. This talent is most evident in the lyrics and lush, string-tinged tone of Yamagata’s latest EP, Heavyweight (out now digitally and Nov. 27 on CD via Yamagata’s Frankenfish Records), a recording that highlights and indulges a rawness that had been absent on her more upbeat (but still heavy-hearted) 2011 release, Chesapeake.

Despite the heartaches, Rachael Yamagata also has a funny side, such as her peculiar onstage banter, or ability to crack a joke at her own expense. She admits to liking Rocky (yes, 1 through 5) and says it helped shape the title of her EP. She also shares tales of her cats she misses while on the road.

After touring this fall in support of Heavyweight,Yamagata will release an EP of covers for Valentine’s Day release before heading to the studio again to work on her next full-length.

We caught up with Yamagata before her sold-out show at City Winery (which will be full of what she describes as “dark, date night material”) to reminisce about her five favorite things the-now-Woodstock, N.Y., resident misses about her dear Windy City she left behind years ago:

1The summer festivals: “I spent years playing them on Lincoln Avenue or in Wicker Park. I was in the band Bumpus for a number of years, and that was really where I really sunk my teeth into live performance and playing with that great chemistry on stage. I miss that experience, definitely.”

2The lakefront: “The lakefront was sort of my nature refuge. I would go running on the lakefront seven miles a day…when I had good knees [laughs], and sit out by the water, and that was a big part of my Chicago experience.”

3The “old”Wicker Park: “Certainly the Wicker Park area—which I hear has changed  dramatically since I’ve been there. The whole environment of different venues. and growing up with The J. Davis Trio and different local acts that were just truly a community of musicians, and feeling very inspired. The Assassins, and Kill Hannah, and that whole going to see bands at the Double Door thing.”

4Wiener Circle: “That place right on Clark Street where they yell at you when you’re ordering and it’s the best cheese fries and burger of your life? … The Wiener Circle. Yes! I miss Wiener Circle, oh my God! That would be a top Chicago fave!”

5Sushi restaurants: “We all used to work at these sushi restaurants—everyone in the band. We spent a lot of time at this place called Tsunami, which was right on Dearborn and Division. And we also worked at Kamehachi on Clark Street, about five feet from Tsunami. I have a lot of memories of the sort of resistant life and that group of friends,  late nights, and then having the folks there come to shows. It was just a great city to experience music and build friendships.”

Tickets for Yamagata’s sold-out show may still be available. Call City Winery for information at (312) 733-9463; $20+. Download or purchase Yamagata’s new EP, Heavyweight, at RachaelYamagata.com

— Chicago Music