Veruca dress, Corey Lynn Calter ($282). Nordstrom, 55 E. Grand Ave., 312-464-1515. Rock candy ring, Ippolita ($1,995). Neiman Marcus, 737 N. Michigan Ave., 312-642-5900. Gold lamé pumps, Giuseppe Zanotti Design ($750). Saks Fifth Avenue, 700 N. Michigan Ave., 312-944-6500

 

Champagne dress, Rachel Roy ($498). Nordstrom, 55 E. Grand Ave., 312-464-1515. Diamond drop earrings (price on request) and ring ($3,850), Tacori. James & Sons, 1845 N. Clybourn Ave., 773-327- 880

With her enormous eyes, long limbs, and a melodic voice that sounds like it’s asking a question even when it isn’t, Judy Greer was built for ’30s screwball comedies, But bit by bit, Greer has tried on just about every character role imaginable: as a nerd (Jawbreaker), a mean girl (also Jawbreaker), a suicidal file clerk (What Women Want), a nervous assistant (The Wedding Planner), a literary muse (Adaptation.), and a member of the Jewish Justice League (The Hebrew Hammer). In just 12 years, she’s done approximately 80 projects in TV and film.

Up until now, Greer has most often been recognized for her outrageous turn as Arrested Development’s Kitty Sanchez, the ditsy secretary given to flashing her boobs and announcing, “Say goodbye to these!” But with a fistful of new projects, it’s obvious that, for Greer, playing Kitty was just a warm-up. Lately, you’ve probably seen her in Two and a Half Men 2.0 as Bridget, the ex-wife who has ruined Ashton Kutcher’s billionaire Walden for all other women. “I was driving by a café on Melrose when I found out I was going to be on Two and a Half Men,” says Greer. “I was like, You’re swear-word kidding me.” After a pause, she clarifies: “I said the F-word.” Greer is also getting some buzz with a dramatic role in Alexander Payne’s much-anticipated bittersweet movie The Descendants, which opens November 18. Considering that Greer learned her craft at DePaul University’s prestigious Theatre School, can Chicago take credit for her success? “You may,” says Greer graciously.

Behind the Scenes: Judy Greer Cover Shoot

Greer grew up outside Detroit, but she spent close to five years in Chicago in the ’90s. “I remember that up until right about now, that was the happiest time of my life,” says Greer. One of her favorite things was to walk on Michigan Avenue late at night after all the stores had closed. “I used to love to go window shopping because I was too broke to buy anything,” she says. “I like that, the memory of nighttime Chicago. In the summer, it’s so magical. It’s so hot out, you feel like [you] could walk around all night long in a sundress with a credit card in [your] pocket.”

DePaul University is where Greer learned to be fearless. “You have to do some really weird things in acting school,” she says. “At the time you’re like, I’m never actually going to have to play the role of a tiger. But not too long ago, I got a part where I had to be a jerk in front of a bunch of people, and I thought, Oh! Maybe that’s what that was about. Being comfortable making an ass of myself—I think that’s what a lot of acting school is.”