Zach Galifianakis stood firm against demands from Hillary Clinton’s team to avoid jokes about her email controversy during a 2016 Between Two Ferns appearance, nearly derailing the interview.

Negotiation Over Comedy Boundaries

During a recent podcast with Conan O’Brien, Galifianakis shared details of the tense setup. Clinton’s team initially instructed him not to mention the emails. He responded that without the freedom to include them, the interview would not proceed.

Surprisingly, the team relented, allowing the comedian to proceed as planned. ‘You have to do it the way we want to do it if you’re coming on a comedy show,’ Galifianakis explained.

He noted Clinton appeared reluctant during the taping. ‘I could tell she didn’t want to be there, and I totally get that,’ he said.

Roasting Highlights from the Show

The interview featured sharp humor targeting Clinton’s emails and her time as Secretary of State. Galifianakis quipped about her title, asking how President Obama liked his coffee—’like himself… weak’—and inquired about her typing speed.

He also pressed if she planned to emulate Donald Trump’s tactics. In one exchange, he asked if Trump won and Kid Rock became Secretary of State, would she move to Canada. Clinton replied she would stay and try to prevent destruction of the United States.

Galifianakis joked about leading a civil war, prompting her denial. ‘I wouldn’t take up arms. That might be a little extreme,’ she stated. He then referenced her gun comments, to which she responded, ‘I really regret doing this.’

Origins and Improvisation

Producer Scott Aukerman revealed Clinton pitched the idea herself, inspired by President Obama’s appearance to boost Obamacare sign-ups among young voters. ‘It was actually her idea,’ Aukerman said. The segment targeted millennials, a key demographic for her campaign.

Most of the content was improvised, catching Clinton off guard at times.

Views on Trump and Comedy

Galifianakis expressed frustration that comedians hosting Donald Trump often fail to challenge him, instead ‘sucking up.’ He and O’Brien agreed Trump appearing open to self-deprecating jokes would humanize him.

Clinton’s gamble on the show aimed to energize young voters but preceded her loss to Trump in the 2016 election.