How Wisconsin Democrats Used Hollywood Reunions to Make a "Critical Difference" in the 2020 Election

Bradley Whitford on 'West Wing,' 'Princess Bride' and Julia Louis-Dreyfus on 'Veep'; Inset: Ben Wikler
Courtesy of Photofest (3); Democratic Party of Wisconsin

Ben Wikler, chair of the state's Democratic Party, speaks to The Hollywood Reporter about how a grassroots effort in August sparked the wave of entertainment and TV fundraiser events that raised millions of dollars in the run-up to Nov. 3.

For the fourth consecutive presidential election cycle, the results from Wisconsin proved to be a nail-biter. In 2016, President Donald Trump won the state by less than a percentage point and now, four years later, his Democratic challenger, President-elect Joe Biden, flipped the battleground state by a similar margin.

That narrow win can be traced back, in part, to a Hollywood virtual reunion movement that began with a grassroots event for Wisconsin Democrats during the Democratic National Convention.

"It’s a state that turned out to be the tipping point in the Electoral College and went for Biden by a little over 20,000 votes," Ben Wikler, chair of the Democratic Party of Wisconsin, tells The Hollywood Reporter of his state's vote count, of which the Trump campaign has said it will seek a recount. "That’s the kind of margin where, if you add a couple thousand volunteers, you can generate that many votes — which these events did."

He then notes, "Things could have gone so differently."

Indeed, a mini West Wing cast reunion event — spearheaded by Wisconsin native and star of the beloved White House drama Bradley Whitford — ended up paving the path for the slate of high-profile entertainment and TV fundraising reunions that would ultimately go on to raise more than $7 million dollars, and court thousands of volunteers, for the state's Democratic party.

"It came about because Bradley Whitford is from Madison and he had done fundraisers for Wisconsin Democrats for decades," says Wikler, who wrote for The Onion and worked for Al Franken's radio show before entering politics. "But this year, because of coronavirus, it didn’t make sense to fly in and get a bunch of people together. That said, he developed an idea with our team [for] our first grassroots, entertainment-themed event."

The virtual West Wing Weekly podcast reunion took place on Aug. 18 and ran alongside the DNC. "Whoever wins Wisconsin will win the electoral college and win the White House. It’s that simple," read the invite from Whitford.

The event raised more than $165,000.

"It blew past our fundraising goals, engaged thousands of people and created a template for us that wound up changing the way Democratic Party organizations fundraise in 2020," Wikler said of the impact.

Wikler and his team realized that having someone who is at the center of the show or film taking the lead to secure both the talent and the rights was the critical piece of the reunion puzzle. "It’s like show business or live theater, where it seems like it can’t possibly work until it suddenly clicks and the magic kicks in," Wikler recalls.

Then, enter Cary Elwes, who Wikler says "made it his personal mission to out-do Miracle Max when it came to miracles." Elwes organized the Princess Bride reunion event with the original cast of the 1987 classic film in mid-September that went on to raise $4.25 million dollars.

"If you look at our plans for the end of the [fundraising] cycle, from before the Princess Bride event to after, it’s a night and day difference," says Wikler of the running list of reunions that would follow the Princess Bride event, including with the casts from VeepHappy Days, Parks and Recreation, Superbad and Rocky Horror Picture Show. "[The Princess Bride] event both transformed what was possible for us and made clear that we should keep our feet on the gas with building grassroots events through the end of the cycle."

With such an influx of funds in the run-up to Election Day, Wikler and his team kept adding to their fundraising program. Weekly meetings were upgraded to daily sessions as Wikler, who credits his finance and digital groups, kept expanding their organizer team and were able to zero in on key electoral work.

"We had a huge voter education push after the U.S. Supreme Court ruled that absentee ballots couldn’t arrive after Election Day," he says. "And after that, we did a massive push with digital ads, as well as with our organizers, to tell people that the deadline to turn your ballot in was Election Day, and I think that made a critical difference in winning Wisconsin."

They also invested fundraising money into state legislative races to energize voters to turn out not only for Biden, but for the candidates down the ballot as well. "Ultimately, while state legislator programs across the country had a really tough time, we were able to achieve our goal of stopping Republicans from winning super majorities in Wisconsin and actually flip two Republican-held state assembly seats," he says. "That money coming in right in the closing months and even weeks of the campaign meant that at the moment when the Republicans do their surprised attacks, we were able to counter."

In those final weeks, Wikler and his team were also fielding calls from other states and consulting on a growing list of reunions. "Anyone involved in one of these events ended up then having ideas for how to do more," he says of the state-to-state interaction behind Hollywood's nationwide push. From a West Wing get-out-the-vote follow-up to a Seinfeld reunion for Texas; Fright Night gathering for Michigan; another mini Veep reunion for North Carolina; and Star Trek, Avengers and Hamilton events put on by the Biden campaign, "the West Wing and then the Princess Bride [events] launched this whole new tactic that was perfectly fitted to the coronavirus era and helped benefit Democrats across the country," he says.

When it came to picking the properties, there was a running list. Wikler says he's grateful for everyone who participated and has no regrets about the ones that got away. But there's also a wish list in play for the next fundraising season. "I don’t want to jinx anything by putting it on the record," he says.

Indeed, Wisconsin is set to remain a critical battleground. Wikler notes that polling shows the state as the most evenly split in the country between Democrats and Republicans, as well as being the only state to have four presidential elections with under 1 percent margins. That means one thing: "As Democrats, we can’t take our eye off the ball just because the White House has been won," he says.

So the plan, Wikler adds, is to keep organizing, keep mobilizing and keep working. And to continue to recruit help from their Hollywood friends across the country to keep the focus on the areas that will make the biggest difference.

"These events were not about the warm fuzzies of awareness," Wikler says of applying the success learned from 2020 to the 2021 and 2022 cycles. "They were about raising money that would benefit strategically targeted electoral work, like signing up volunteers and completing thousands of shifts doing virtual phone banking and text banking. It was a way that entertainers and cultural icons and artists could use their talents to draw people in who would then be mobilized to do some of the highest-impact work anyone could do in the country."

He concludes, "If you look at the math coming out of this election it is crystal clear that no effort was wasted in the content."