How You Know Her: As Gilly, Aunt Linda, the Target lady, Penelope, or one of 20+ characters she played on her seven-year stint at Saturday Night Live (SNL) that launched her to superstardom as one of the reigning queens of comedy. After SNL, Wiig graduated from sketch comedy to big-screen star when she proved that women can play just as dirty as guys in Bridesmaids—and earned an Oscar nomination for best screenplay in the process.
What You Don't Know: At age 20, she spent three months building fires, hiking mountains, and teaching wilderness survival skills at the National Outdoor Leadership School (similar to Outward Bound), but after a semester of soul-searching she was still unsure of her future—acting never crossed her mind. When she made it back to civilization, she applied to the University of Arizona for "a boyfriend thing" and to study art.
After graduating, she was hired at a plastic-surgery clinic to sketch clients' post-op bodies but made a snap decision to leave for Los Angeles to pursue acting instead. Her experience at that point? An intro-level acting class she took for credit in college.
Where You'll See Her Next: You can see the 39-year-old kissing Darren Criss in Girl Most Likely (out July 19), in which she plays Imogene, a woman who can't catch a break as a Manhattan playwright and is forced to move back home with her eccentric mother (Annette Bening). Along the way, Imogene fakes her own suicide, walks through a casino in a hospital gown, and gets romantically entangled with the Glee star—who's 14 years her junior.