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Chicago has a rich musical past, so it only makes sense that Wilco's Jeff Tweedy, the owner of perhaps the richest musical presence around, makes his home there.

"I THINK THIS might be the toughest interview I've done," Jeff Tweedy offers with a chuckle.

It's a somewhat surprising comment, coming from the well-traveled Wilco front man. In addition to being the subject of a major biography (Greg Kot's Wilco: Learning How to Die) and of a feature-length documentary (Sam Jones's I Am Trying to Break Your Heart), Tweedy has been the focus of countless articles and press inquiries over the years.

That kind of critical support has helped grow the 39-year-old singer-songwriter's original small cult of fans (from his days in the alt-country combo Uncle Tupelo) into a legion of diehard Wilco-heads, even as Tweedy has continually challenged both his audience and himself musically. A somewhat reluctant rock star, he's managed to toe the fine line between underground respect and mainstream success and has become one of contemporary music's most compelling and revered figures in the process.

Jeff Tweedy's essential Chicago spots

, Southern, inexpensive to moderate, (773) 489-4600
Lou Malnati's Pizzeria, Italian/pizza, moderate, multiple locations, www.loumalnatis.com
Lou Mitchell's, diner, inexpensive, (312) 939-3111, www.loumitchellsrestaurant.com
Shiraz Restaurant, Middle Eastern, moderate, (773) 777-7275, www.shirazrestaurante.com
Superdawg, hot dogs/burgers, inexpensive, (773) 763-0660, www.superdawg.com
Tank, sushi, Japanese, moderate to expensive, (773) 769-2600, www.tanksushi.com

Auditorium Theatre of Roosevelt University
, (312) 922-2110, www.auditoriumtheatre.org
Empty Bottle, (773) 276-3600, www.emptybottle.com
Hideout, (773) 227-4433, www.hideoutchicago.com

Midwest Buy and Sell
, (773) 545-2020, www.mwbuynsell.net
Quimby's Bookstore, (773) 342-0910, www.quimbys.com

Chicago Park District,
(312) 742-7529, www.chicagoparkdistrict.com
Lollapalooza, (888) 512-7469, www.lollapalooza.com
Old Town School of Folk Music, (773) 728-6000, www.oldtownschool.org
Pitchfork Music Festival, (866) 468-3401, www.pitchforkmusicfestival.com

Electrical Audio, (773) 539-2555, www.electricalaudio.com/

Soma Electronic Music Studios, (773) 342-9964, www.somastudios.com

A native of tiny Belleville, Illinois, Tweedy has called Chicago home for the past 13 years. He arrived in the early 1990s, ostensibly to be with his girlfriend, who is now his wife, Sue Miller. She was a co-owner of the much-beloved and now long-defunct rock club Lounge Ax. Longtime North Side residents, the Tweedys have two sons, Sam, seven, and Spencer, 11; the latter, already following in his father's footsteps, is a member of kiddie rock band the Blisters.

Tweedy's group, Wilco, meanwhile, has just released its sixth studio album, Sky Blue Sky. Recorded in the band's loft studio rehearsal space, the disc finds Tweedy once again exploring a stylistic shift - the album luxuriates in the sweet sounds of '70s FM radio and has a warm, rootsy bonhomie.

A proud and passionate Chicagoan, Tweedy offers his insights on the city's music scene, his favorite family dining spots, the best places to pick up a guitar, and where to see a show. And he also tells why he doesn't do much record shopping anymore.

Being a native Midwesterner, did you spend a lot of time in Chicago when you were a child?
Well, I grew up about five hours south of Chicago, near St. Louis, so I didn't really come here as a kid - it would've been like going to Mars. [Laughs]

The first time I really came to Chicago was with Uncle Tupelo in the late '80s. We started playing at a club called the Cubby Bear and then at the Lounge Ax, which is where I met my wife, Sue. We were dating, but it was hard to consider ourselves a real couple unless we lived in the same city. So when Uncle Tupelo broke up and Wilco started, that kind of seemed a good time to make a change, so I moved to Chicago.

Did anything surprise you about the city when you arrived, in terms of coming from a smaller town like Belleville?
By the time I moved to Chicago, I'd certainly had my eyes opened to the rest of the world, just from touring so much. But the thing that struck me the most when I spent time in Chicago was the sense of community among musicians here. The rock community was really vibrant, and the fact that there were so many people happily coexisting with each other surprised me, I guess. I've never really been much of a scene guy, and I don't think I am now, but it was nice to see that there was a real thriving element to the way people were living with each other and making music.

It's a place that has always had a tremendous legacy as a musical city.
Chicago has an unbelievable history through the years. Things that stick out in my mind immediately are Howlin' Wolf and Hubert Sumlin, Mavis Staples - people like that. All these artists who made their home here form a huge part of my record collection.

It continues to be a great place for musicians - and not just for rock or pop musicians. There's an unbelievably vibrant improvised music scene here centered on clubs like the Empty Bottle. Chicago is really the center of the universe for that kind of music. I don't even think any cities in Europe can compare to what we have here.

Do you think that being in Chicago - as opposed to being in New York or in Los Angeles - has been helpful to your music and career?
Chicago is pretty great for a lot of reasons, in my mind. If you're in a band, there are tons of places to play. Compared with other major cities, you can live reasonably well without a lot of money. And there are a lot of people who are very good at recording - there are great studios all over town, like Electrical Audio and Soma [Electronic Music Studios].

Even for us, having our own place to record at, it's very helpful to have someone just a couple of blocks away who can lend you a reel of tape or come over and help troubleshoot if your machines aren't working. There's a great support system in that way. I feel very comfortable here, very taken care of and nurtured as a musician. It makes it an easy environment to be creative in.