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How Kristen Wiig Made Her Way From ‘SNL’ to Dramedies ‘Skeleton Twins’ & TIFF Premiere ‘Welcome to Me’

How Kristen Wiig Made Her Way From 'SNL' to Dramedies 'Skeleton Twins' & TIFF Premiere 'Welcome to Me'

Why have women alums of “Saturday Night Live” had a harder time than men, who’ve monopolized the show over the years, at making a permanent dent at the movies?

That situation has shifted somewhat recently with the in-roads made by Tina Fey and Amy Poehler, who co-starred with success in 2008’s “Baby Mama” and 2004’s “Mean Girls.” Still, their richest opportunities have come in the form of TV series: Fey on “30 Rock” and Poehler on “Parks and Recreation.” 

But funny-lady Kristen Wiig seems to be making many of the right moves to establish herself as a movie actress who can do more than just silly comedies.  Evidence of her growth arrives this weekend in the form of “The Skeleton Twins, “ an unexpected highlight at the Sundance Film Festival earlier this year.  With Wiig joining forces with SNL buddy Bill Hader as siblings Maggie and Milo, who reconnect after his failed suicide attempt, both actors are earning some of their the best reviews ever for this touching, humor-laced drama.

“The biggest surprise for audiences expecting plenty of laughs will be just how effectively both thesps handle the weightier dramatic material,” wrote Variety critic Geoff Berkshire. Even though Hader has more screen time, “Wiig is no less impressive as a woman quietly falling apart. … There has always been a touch of sadness to Wiig’s comic characters, and she nails Maggie’s hushed desperation and more explosive acts of frustration.”

Signature line: “Don’t ask an actress if she’s ready, unless you want to get a face full of ‘here we go!” – Wiig in a “Saturday Night Live” skit as Broadway diva Mindy Elise Grayson on the game show “Secret Word.”

Career peaks: It took a while for the introverted Wiig, now 41, to be ready to say “here we go!” and embrace her showbiz destiny.  As an art student at the University of Arizona, she signed up for an elective acting class and was encouraged by her teacher to consider a performing career. She quit her first post-college job — drawing “after” pictures at a plastic surgery clinic – and headed to Los Angeles.

It wasn’t until she caught a performance by the improv troupe The Groundlings–where the likes of Will Ferrell, Maya Rudolph and Jon Lovitz got their start–that she found her calling. Wiig auditioned and joined the group, inventing several of her trademark sketch characters such as the excitable Target lady and grouchy critic Aunt Linda.

“SNL” honcho Lorne Michaels soon recruited her and she joined during the show’s 31st season in 2005. Her wide array of popular characters included naughty schoolgirl Gilly and tiny-handed “Lawrence Welk” singer Dooneese as well as impressions of money maven Suze Orman and Speaker of the House Nancy Pelosi.

After a small role in 2006’s “Unaccompanied Minors,” Wiig made a bigger impression the next year as a passive-aggressive TV exec who gives Katherine Heigl’s on-air talent a hard time in Judd Apatow’s hit “Knocked Up.” She soon was hired for a series of supporting roles in mainstream comedies, including Ferrell’s “Semi-Pro” (2008), Drew Barrymore’s roller-derby-themed directing debut “Whip It” (2009) and Tina Fey and Steve Carell’s “Date Night” (2010).

Wiig finally got the chance to fully showcase her talents as an actress, screenwriter (along with pal Annie Mumolo) and co-producer thanks to director Paul Feig (“Unaccompanied Minors”) and Apatow who collaborated with her on the female ensemble comedy “Bridesmaids” (2011). As a down-on-her-luck maid of honor, Wiig broke the gender barrier with an R-rated romp, provided Melissa McCarthy with a deserving breakout role and rewarded herself by taking the lead as a 30-something woman who is utterly relatable despite her self-defeating habits. The film remains Apatow’s highest-grossing production, with a worldwide box office of $288.4 million.

New York critic David Edelstein was among those impressed:  “Wiig’s gift is for putting on a mask of blandness that regularly slips to reveal panic, crazed insecurity, jealousy, and anger  — and her blandly pretty face is rubbery enough to disarm you with its range of lunatic expression.”     

Biggest assets: When it comes to funny ladies, Wiig is the antithesis of Jennifer Aniston, Cameron Diaz and Kate Hudson: all talented, all pretty and all pretty much predictable. Though actually quite attractive, Wiig likes to go out of her way to make herself look unappealing, fearlessly playing up her characters’ worst traits. As she herself has said, “It’s fun for me to play people who are just kind of odd.” Wiig is often better served in indie films that benefit from her sometimes unsettling blend of pathos and comedy–most notably 2009’s coming-of-age story Adventureland, which featured Hader as well. She is also an in-demand and highly-regarded voice actress, as heard in the “How to Train Your Dragon” and “Despicable Me” franchises.

Awards attention: Oscar-nominated along with Mumolo for best original screenplay for “Bridesmaids”; Golden Globe-nominated as Best Actress in a Comedy or Musical for “Bridesmaids”;  and nominated for seven Emmys, including five times for her work on “Saturday Night Live.”

Biggest problem: It didn’t matter so much when Wiig was a supporting player in such barely-seen films as 2007’s “The Brothers Solomon” and 2010’s “MacGruber.” But since her stock soared post-“Bridesmaids,” she really needs to be choosier. Not even critics could get behind this year’s “Hateship Loveship,” even though many thought her portrait of a forlorn housekeeper with surprising fortitude was far better than the film itself.  But Wiig was not spared from the slings and arrows tossed at 2013’s “Girl Most Likely,” which uncomfortably saddled her with boyfriend problems and a zany mom in the form of Annette Bening. The box-office take of $50,600 says it all.

Biggest misfire: Considering it was once tagged as a possible Oscar contender before it was screened and grossed only $58 million domestically on an estimated $90 million budget, last year’s “The Secret Life of Walter Mitty” with Ben Stiller directing and starring did little to boost Wiig’s profile. Still, critics — as they are wont to do in her case — treated her low-key portrayal as the title hero’s office dream girl with more respect than the film itself.

Gossip fodder: “I enjoy being characters rather than myself,” says the ever-discreet Ms. W. Which is why she rarely divulges details about her personal life, including about her four-year marriage to actor Hayes Hargrove that ended in 2009. That hasn’t kept the tabloids from keeping tabs on Wiig’s love life, however. She dated producer-actor Brian Petsos for a while before moving on to Fabrizio Moretti, the drummer for The Strokes who used to date Drew Barrymore (a situation that Wiig’s “Whip It” director called “whacky” and “incestuous” but also “fitting”). Wiig and her drummer boy stayed together for 18 months until calling it quits in 2013.

Career advice: This sister should be doing it more for herself. Namely, Wiig needs to become more involved behind the scenes, especially since she is no longer tied down by her “Saturday Night Live” duties. Being one of the best things in a mediocre or worse vehicle isn’t going to get her very far beyond where she is now. Although you do have to admire how she refused to do a knee-jerk sequel to “Bridesmaids” just for the money. But what’s even better was the fairly recent news that she and Mumolo are writing a female-driven buddy comedy to co-star together in that is expected in 2016 – and Wiig is angling to direct.

What’s next: Wiig’s “Welcome to Me,” which premieres this weekend at the Toronto International Film Festival, continues her run on more daring drama-oriented material as a sufferer of Borderline Personality Disorder who decides to toss her meds and have her own talk show after winning a big lottery jackpot. As she revealed in the recent “Elle” magazine, the role required her to totally disrobe in one pivotal scene. It is directed by a woman, Shira Piven – wife of frequent Ferrell collaborator Adam McKay – so one hopes she does well by her star. The rest of Wiig’s dance card is filling up as well, with everything from “Nasty Baby,” a surrogacy drama by Chilean filmmaker Sebastian Silva (“Crystal Fairy”), to “The Diary of a Teenage Girl,” a coming-of-age drama based on a graphic novel with Wiig as a mother whose boyfriend (Alexander Skarsgard) is sleeping with her underage daughter.

Wiig isn’t giving up completely with straight-on comedy, however. The once-titled “Loomis Fargo,” directed by Napoleon Dynamite’s Jared Hess and co-starring Zach Galifianakis and Owen Wilson, is based on the real-life heist of an armored trunk in which the robbers made off with close to $20 million in cash. 

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