Michelle Wolf’s career trajectory — with one notable exception — isn’t that different from a lot of comics who are managing successful careers. It starts with an unsatisfying day job, which leads to dabbling in improv, and then to stand-up, where the really good ones might get noticed, land TV writing gigs and earn occasional on-camera appearances, leading to bigger roles and maybe even a stand-up special. But while that path could describe a lot of comics, a moment when suddenly everyone knows your name, for better or worse, happens only to a few.
Wolf, who drops by the Wilbur Theatre for stand-up sets Sunday and Monday, says the year’s highlights — including her highly publicized stint as host of the White House Correspondents’ Association dinner, when everyone in the country, it seemed, was picking sides about whether she had gone too far — have been the result of hard work, dedication, and luck.
“I know friends of mine who have been doing [comedy] for 10 or 15 years,” she says on the phone from her native Pennsylvania. “A lot of it was timing that just worked out really well. I was able to get a job that let me do stand-up, and I got fired from a job on purpose because I got severance that let me do more stand-up. . . . The timing for everything was just right.”
That job was in client services at Bear Stearns in 2008, during the depths of the nation’s financial crisis. She says that while some her colleagues were nice and had positive intentions, it was an atmosphere largely fueled by cutthroat competition.
“It was a good job, and it let you live in New York for a few years. I thought I’d see how that went.” However, she says, she soon found that “everyone was always mad and looking to blame other people. I was literally watching people lose their 401(k) and their job, so everything they worked for was gone. Meanwhile I’m young — if I lose my 401(k), I have decades to build it back up. It wasn’t fun.”
One night, a friend took her to a “Saturday Night Live” taping, and it occurred to her that comedy would be a fun thing to try. She started by Googling the cast members to find out how they got started, and she found that most of them came up through improv comedy. So Wolf enrolled in classes at the Upright Citizens Brigade Theatre and loved it. From there, she pursued stand-up, and before long a producer from “Late Night With Seth Meyers” took notice and asked her to join the writing staff. Since the show was in its early stages, Wolf was part of the team that helped “Late Night” develop its voice. She sometimes appeared on camera, most notably as “Grown-Up Annie,” the jaded, middle-aged version of the ever-chipper Little Orphan Annie. (In one typical appearance, her reply to why she was wearing sunglasses inside was that “the sun will come out tomorrow, and I just can’t even.”)
Wolf eventually left “Late Night” for “The Daily Show With Trevor Noah,” where she mostly commented on the absurdity of double standards in gender politics. Her takes on the then-emerging Harvey Weinstein scandal especially garnered Wolf some attention; she also wrote and delivered commentary on the all-male legislative panel on women’s health care (“Thirteen white guys and no women. . . . You’d think they’d at least put Mike Pence in that group so his wife would have to be there, too.”).
Wolf says her writing experience has been invaluable for her stand-up act, which skewers the same subjects, albeit from a more personal angle.
“Especially at ‘Late Night,’ you’re writing a high volume of jokes every day about a variety of things,” she says. “You’re doing political, topical, weird stories, and you just have to deliver every day. You have to figure out how to be funny every day.”
You also have to be resilient, which surely came in handy after delivering a raw, blisteringly funny address at the correspondents dinner last April. Though much of the criticism directed at Wolf claimed that she went too far (critics inaccurately pointed out, for example, that she mocked White House press secretary Sarah Huckabee Sanders’s appearance), but Wolf is steadfast. Her target, she says, was the media that had grown complacent with what she views as a dishonest presidency.
“The biggest problem,” she says, “isn’t necessarily the administration but the fact that the media is completely obsessed with him. And not everyone’s doing their job, not just reporting the news. Because it’s good for sales. I wanted to point out what the media was doing, which was that they’ve made a lot of money and been very successful off of [President] Trump. It’s been good for everyone involved except the people. It’s been good for him, and TV, and newspapers.”
Meanwhile, the White House Correspondents’ Association has decided its next host will be a historian, breaking with the long tradition of comics providing the entertainment at the dinner.
Though Wolf’s speech generated angry tweets from the president and brought her some unwanted attention, it also raised her profile even higher. Last spring, she hosted a 10-episode series for Netflix titled “The Break,” she had her own HBO stand-up special (the hilarious “Nice Lady”), and her stand-up career continues to flourish. Wilbur owner Bill Blumenreich calls Wolf “a great young comic with a bright future. We are excited to be hosting her.”
Wolf says the two Boston shows, the second of which will ring out 2018, will feel as much like a celebration as possible.
“There’s going to be a DJ and a couple of special guests,” she says. “I’m definitely going to dress up and try to make it like a party.”
At the Wilbur Theatre, Boston, Dec. 30 (sold out) and Dec. 31, 7 p.m. Tickets: $37, www.thewilbur.com