Wolf rededicated herself to standup comedy over the past year in the aftermath of her scathing White House Correspondents' Dinner speech in April 2018 and the quick cancelation of her Netflix talk show The Break. "I’ve gotten to spend this last year just doing standup for the first time in my career," she tells The Daily Beast. "And I’ve had so much fun. It’s probably been the best year of my life. And I think it’s also reflected in the special. I think you can tell I’m having a good time. I know a lot of people loved me from the Correspondents’ Dinner, I know a lot of people hated me from the Correspondents’ Dinner, and I just hope when people watch this special they just get converted to fans of my comedy." Wolf says that after doing the White House Correspondents' Dinner, "people just assumed that I was a political comedian. And it’s a weird thing to make an assumption about, because I was hired to do a job; a job I’m still very proud of, and a job that—I don’t think they thought I was going to do it that way. But I can write jokes about any subject. You give me a subject and a half-hour, I’ll give you 10 jokes. It doesn’t mean I’m a political comedian, it just means I know how to write political jokes. But they’re also not my favorite type of jokes to write. I like more social commentary, and of course those end up being political issues as well but that’s only because life is political. I also find political jokes, at this point, to be kind of boring and just so one-note. I’m just so sick of hearing about it. It doesn’t interest me to do it right now. I’m not saying it won’t in the future but it’s not my favorite topic." Wolf admits that her political turn at the Correspondents' Dinner spilled into The Break, which premiered one month later. "After the Correspondents’ Dinner, I let that seep in to the show more than I wanted it to," she says. "I genuinely wanted the show to be a 'break' and just be silly and funny but that didn’t seem to be what people wanted at the time. People wanted me to talk about politics and those big, hot-button issues. That being said, I’m not unhappy with anything we did. I look back on some of the stuff and I think it’s very, very funny."