Cinematic Chicago is that of John Hughes comedies or grittier fare like The Fugitive and The Untouchables, but when given the chance, the Windy City can provide just as lovely a backdrop as any typical American metropolis.With its picturesque Lake Michigan views, famous sports stadiums, cozy bars and snow-caked El platforms, a Chicago setting can lend even a mediocre date movie something authentic—where Old Style, Italian beef and Jim Belushi can even be (somehow) romantic.Stu Zicherman ( is designed as an anthology series, with each season focusing on a different protagonist’s journey through modern dating and relationships.Richard Tanne’s recently released romantic indie Southside with You is an unassuming date movie with two larger-than-life characters—Barack and Michelle Obama—at its center.The City—it becomes obvious—is James’s great love, the one that will ultimately motivate him to lower his expectations and seek contentment where he is. Return to Me Director: Bonnie Hunt Year: 2000 Directed by Chicago-based actress Bonnie Hunt, Return to Me is a quaint romantic comedy modeled on the classics of the studio system era.
In standard Joe Swanberg fashion, Drinking Buddies uses subtle gestures—a lingering glance here, an offhand comment there—to highlight the deep differences in the ways these characters view themselves and their relationships with one another.The appeal of I Want Someone to Eat Cheese With lies in its rambling, Slacker-esque, quality.James spends much of the movie in the streets of Chicago: eating junk foodon top of his car near Wrigley Field, strolling through Roscoe Village with his best friend (David Pasquesi), handing out hot dogs at Budaki’s Drive In, or chatting with Beth in Millennium Park.Meanwhile, ignore the casual misogyny mostly perpetuated by Dan’s odious best friend, played by the aforementioned Jim Belushi.The film has a field day with its Chicago setting, with magic hour softball games in Grant Park, a Cubs game viewed from a rooftop, lunch outside Kelly’s Pub as the El rattles by, and the whole range of seasons and holidays, allowing for blizzards and torrential rains—all the dramatic Chicago weather to match our leads’ tumultuous relationship. I Want Someone to Eat Cheese With Director: Jeff Garlin Year: 2006 I Want Someone to Eat Cheese With is a low-key, not-quite-romantic comedy about James (Curb Your Enthusiasm’s Jeff Garlin), an overweight, struggling actor who lives with his mother and is searching for something more: that great movie role, that loving girlfriend, that diet that lasts.
It’s a small film, but one that effortlessly and accurately captures a familiar emotional predicament, as well as an ultra-specific “scene”—Chicago craft brewing—at an ultra-specific time. While You Were Sleeping Director: Jon Turteltaub Year: 1995 While You Were Sleeping, a throwback romantic comedy in the screwball mode, is impossible not to like, a standout of the genre that holds up more than 20 years after its release.