How do you pack a year full of comedic political commentary into one standup act?
You can find out how Lizz Winstead does it at her annual year in review show, returning to the Cedar for three performances Dec. 30 and 31.
Brassy and biting, Winstead’s overview of what happened in the past year is a real treat, and a perfect New Year’s or day-before-New Year’s date. It’s a great way to release all of the infuriating, bizarre, hypocritical and out-there stories that happened over the past year in politics and in popular culture.
As an added bonus, you get to hear the finger-style acoustic guitar player of Sam Breckenridge, who happens to be Winstead’s nephew.
The Southwest High School graduate, a co-creator of The Daily Show and co-founder of Air America Radio, is doing her ninth year-in-review show.
“It’s a really great way to just take the whole year and lay it out,” she said. “I do shows throughout the year and develop material, and then I orchestrate it to just kick it out the door.”
Winstead started doing year-in-review shows under the Obama administration.
“It’s so funny the way things have changed so much,” she said. “I’m one who doesn’t pull punches, so I’ll call people out even when I like them.”
When she first started out, there’d be about 20 news stories in a year that she could touch on throughout the course of the 90-minute show, taking a deep dive into each of those stories.
“But now with Trump it was like every 15 minutes there’s a news story. … I could do a year-in-review show about this week. The Mueller investigation could be a show. Just Trump and his relationship with our friends overseas could be a show.
“At some point it’s like: ‘Wear pajamas. I don’t know when we’re leaving.’”
Last year’s show, in the wake of Trump’s election, was the hardest she’s ever done, she said.
“It was basically a million policies against people who were vulnerable, and then sprinkled in with a bunch of ‘#metoo’ horrible people, and then more horrible policies,” she recalled.
This year? She feels a bit more hopeful.
“This year started out with a bunch of horrible policies, but then we built up to maybe some sanity with our election, so I feel like there’s a positive moving forward,” she said.
That’s right — Winstead feels hopeful as she looks toward 2019.
“What I feel hopeful about is the fact that, first of all, the mid-term elections had general election turnouts, which was really cool,” she said, adding that Minnesota had the No. 1 turnout in the nation.
She also feels inspired that so many non-politicians decided to run this year.
“They were regular citizens who said, ‘You know what? If I want to make change, it’s my government and I’m going to run,’” she said. “And now we are going to see what happens with actual citizen government rather than party-appointed people. I think that’s what people want, and that’s what people were frustrated by.”
When she’s not doing comedy, Winstead is fighting for reproductive rights through her advocacy group, Lady Parts Justice. She sees activism as an addition to what she’s always done, rather than a new direction.
“It’s not an either/or thing. It’s emerging,” she said. “I’ve since the ’90s been somebody who looks at the political landscape and uses my humor to talk about it.”
When she worked for national TV and in corporate broadcasting it wasn’t her job to have a call to action.
“You can make jokes, you can skewer people, but you can’t be an activist,” she said. “That’s the part that was missing from the stuff that I did.”
She loved her job, to a point. Now she still makes satirical videos, goes on the road to tell jokes and points out hypocrisy, but she also gets to tell people how they can make change.
“So now I feel like I have the full career that I always wanted,” she said.
The annual performance ends with a fundraising ask, but mostly it’s just a super-fun comedy show.
Winstead usually tapes the show but says goodbye to the material after it’s over. After spending a year developing it, “I sort of say goodbye to that material and I star writing new the next day,” she said. “For me it’s a good way to get it all out.”
Winstead doesn’t do New Year’s resolutions, but she does have hopes for 2019.
“I’m looking for the truth to be revealed,” she said.
I Really Don’t Caravan, Do You?
When: 2 p.m. and 7:30 p.m. Sunday, Dec. 30; 7:30 p.m. Monday, Dec. 31
Where: The Cedar, 416 Cedar Ave. S.
Cost: $45 in advance or $55 at the door. VIP tickets, including premium seating and a post-show meet and great with Winstead, are $65.