Target Lady – “Saturday Night Live,” 2005
Wiig started playing the talkative cashier in sketch shows at The Groundlings Theatre, and included the character on her “SNL” audition tape. When the character debuted on the show in 2005, it was a breakout moment for Wiig, and Target Lady would appear on the show nine times. But even though the audition tape clearly did its job getting her on the show and giving her her first standout role, Wiig refuses to watch it. “I’ve never even seen the tape that they sent in, because I don’t like watching myself. You never think they’re going to say yes,” she told The New York Times in 2013.
Dooneese – “Saturday Night Live,” 2008
Dooneese Maharelle is one of the four Maharelle sisters who sing on SNL’s version of “The Lawrence Welk Show.” But unlike her sisters, who are beautiful and flirtatious, Dooneese has a huge forehead, tiny hands, a prominent canine tooth and a warbly singing voice. She also tends to go off-topic in her verses, singing about putting worms in her bed and keeping peanut butter in her ears while her sisters sing about going on dates. For those of us who feel out of place in our families, Dooneese is a reminder that it could be worse!
Gilly – “Saturday Night Live,” 2009
Love her or hate her, the mischievous elementary schooler is one of Wiig’s most recognizable “SNL” characters. Gilly has a habit of disrupting class in elaborate and violent ways and only admitting to them when the teacher, played by Will Forte, scolds her. Gilly hosted the “SNL” holiday special in 2009 and appeared on the regular-season show five times, always using her catchphrases (and maybe the only words she knows): “What?” “Mmm-hmm,” and “Sorry!”
Kat – “Saturday Night Live,” 2009
Wiig appeared with Fred Armisen as Garth and Kat, a holiday-themed musical duo who never had their songs prepared. The Weekend Update segment was one of the few completely improvised segments on “SNL,” with Wiig trying to follow Armisen’s lead as he made up increasingly incoherent songs. Wiig talked about the unique nature of the segment in a 2011 interview with Movieline: “It’s the most fun I have because so much of the show is writing, working, deadlines, trying to figure things out, punching up your sketch, knowing you’re going to perform live. And that two and a half minutes of airtime is so freeing and fun.”
Mindy Grayson – “Saturday Night Live,” 2009
Mindy Grayson is a ditzy Broadway actress who can never understand the one rule of the game show “Secret Word.” Over the course of nine appearances on “SNL,” Mindy never wins the game, but does tell the audience a lot about her prestigious stage credits, like “Sassy Slacks of 1963,” “D Is for Dignity” and “I Do Declare My Name is D. Claire” — all of which, she assures, were hits.
Anastasia Sticks – “Saturday Night Live,” 2009
In another iconic pairing, Wiig played a host of the fictional celebrity gossip show “Hollywood Dish” with Bill Hader. The phony reporters interviewed celebrity guests like Scarlett Johansson and Jennifer Lopez, reacting to their answers in increasingly over-the-top ways and eventually re-editing their answers for maximum scandal potential.
Paulette – “Adventureland,” 2009
Wiig teamed up with “SNL” co-star Bill Hader in 2009’s romantic comedy “Adventureland,” playing a mild-mannered amusement park manager. Though she is commonly eclipsed by her husband and assistant manager, played by Hader, the quietly funny Paulette supports her employees, played by Jesse Eisenberg and Kristen Stewart, during a madcap summer at a local theme park.
Vicki St. Elmo – “MacGruber,” 2010
Based on the “SNL “parody of “MacGyver,” 2010 action-comedy “MacGruber” stars Will Forte as the titular secret agent and Wiig as his work partner and love interest. The scene where Vicki impersonates MacGruber in a sting operation at a coffee shop, nervously ordering a large Tazo tea while MacGruber whispers instructions to her through a wire is one of the most underrated comedy scenes of the last decade.
Annie Walker – “Bridesmaids,” 2011
2011’s “Bridesmaids” brought Wiig from “SNL” mainstay to big-screen lead, and for good reason. In addition to writing the screenplay for the ensemble comedy with Annie Mumolo, she starred as Annie Walker, who deals with the painful responsibility of being the maid of honor for her best friend’s wedding. The film was produced by Judd Apatow and surpassed “Knocked Up” as the top-grossing Apatow production to date.
Liza Minnelli – “Saturday Night Live,” 2012
Wiig’s Liza Minnelli impression may only made it to air once, in one of the simplest — and possibly strangest — “SNL” sketches ever seen, 2012’s “Liza Minnelli Tries to Turn Off a Lamp.” It’s just Wiig’s Liza Minnelli…trying to turn off a lamp. And constantly being distracted by her elaborate, Fosse-esque choreography while her husband, played by Jonah Hill, loses patience. It’s perfect.
Patty Hearst – “Drunk History,” 2013
Okay, so heiresses, kidnapping victims and self-proclaimed “urban guerillas” are not exactly known for their comedic potential. But when Wiig takes on the role of Patty Hearst in a 2013 “Drunk History” episode narrated by Natasha Leggero, it works. Leggero’s explanation of the Sybionese Liberation Army and Stockholm syndrome gives Wiig a lot of space to demonstrate her physical comedy chops, even as the narration fades into liquored-up incoherence.
Cynthia Morehouse – “The Spoils of Babylon,” 2014
Wiig earned an Emmy nomination for her portrayal of Cynthia Morehouse, an oil baroness madly in love with her brother, Devon Morehouse, played by Tobey Maguire. The 2014 miniseries was a melodramatic parody of the “TV event” miniseries that were prevalent on network television in the 1970s and 1980s. The eight-episode series is presented as if it had been a real miniseries, complete with the fictional author, played by Will Ferrell, introducing each episode as Cynthia and Devon take their forbidden love from the Texas oil fields to elite boardrooms in New York City.