In 2018, we all seem to be living in dog years, each of Earth’s spins around the sun actually counting as seven. Remember last year when "Mario Kart" and Toad trended on Twitter for the worst possible reasons happened? (It was barely two weeks ago.) Or the Trump/Kim Jong-un meeting two years ago? (Note: It was just June.) Hell, Trump texting the entire nation feels like it was just yesterday. Oh, that was just yesterday? Nothing makes sense.

But if you think your year’s been hard to keep up with, imagine Michelle Wolf’s past 365 days. 

Less than a year ago, her first stand-up comedy special, "Nice Lady," made its debut in December, which quickly escalated to the comedian touring the globe with Chris Rock, to opening for Jon Stewart and Dave Chappelle, to finding herself in the middle of one of the 45 political stories breaking per day when she started a mild media maelstrom with her scathing performance at this spring’s White House Correspondents Dinner.  

After all of that excitement, Wolf earned herself a break. Sorry, not a break, but "The Break," a weekly late-night style Netflix show Wolf hosted and produced, nabbing solid critical acclaim during its 10-episode run. (The streaming service unfortunately didn’t pick up the show for a second season.)

"I really packed a lot in," Wolf laughs, during our phone conversation. "I think that’s one of my general downfalls: I have a hard time not working. Even when I’m ‘taking a break,’ I’m like, ‘What could I be writing?’ It’s always better for me to be busy. I don’t think we want me to have too much free time to really sit around and think."

And now Wolf is back on the road, including a stop at Turner Hall Ballroom in Milwaukee on Sunday, Oct. 7 to work on her latest hour, with another new comedy special in the works barely a year after the first launched her rise. In between all of that, she thankfully had time to chat with me about her insane year, working with Netflix on "The Break" and the aftermath of her Correspondents Dinner set 25 years ago. (But actually it was just April.)

OnMilwaukee: It sounds like you expected some of the aftermath of the Correspondents Dinner, that the room was notoriously rough. But were you prepared for what people would take offense to? Obviously the smoky eye joke got the most press; did you see that coming?

Michelle Wolf: Not at all. I thought that was one of the tamest jokes of the night. There’s definitely other ones in there that I thought being could’ve gone after – legitimately gone after – instead of that one. But yeah, it’s one of those things where someone asks you to roast a room, and then you do that to the best of your ability – and then people are like, ‘We didn’t like you roasting the room.’ (laughs) Well, maybe don’t have that be the requirement.

I think part of the thing is that I went after the media, and I don’t they liked what I said. So in order to take focus off of the part I said about them profiting off of Trump, they made a big stink over the smoky eye stuff just to kind of derail where the conversation would go. Because if people pointed out that they were profiting off of Trump, they might not be able to do it anymore. And they like making money. (laughs)

Afterward you noted in interviews the bizarre vibe of the room was so chummy, between these #Resistance news people being friendly with the same people they decry.

It really put into perspective how the 24-hour news networks – whether they’re liberal or conservative – aren’t news networks. They’re entertainment channels that are trying to peddle "news" as entertainment. If they were actual news networks, they would present the information and that would be it. There would be no panel discussions. There would be no hour-long deep-dives into why this does or doesn’t matter, because they’ve created all this faux controversy – which is a little bit insane because there is so much actual controversy. They’ll spend days talking about a Trump tweet when it’s like, did we really need to dissect that for days?

When I watch the news, I try to watch a BBC, where it’s a very boring and straight-forward – for the most part – presentation of information. It’s not, "At this hour, breaking news, the same thing we’ve been talking about for the last three hours but with live spin on it."

"We have new panelists on, so it’s breaking news again."

Exactly. And to see them all in the room and they’re all getting chummy with either Kellyanne or Sarah Huckabee, and it’s like, oh, this is for you guys. You guys are happy to be doing this, and you don’t realize the real-world consequences for the actual people who are suffering or taking what you say seriously. There’s people on the other side of this, and it was really gross to see that kind of display of comradery between people that are supposed to be "foes." 

I’m impressed you got away with calling Trump broke without getting a tweet about that. I thought that would be the real stinger for him.

Thanks! (laughs) When you’re coming up with Trump jokes, it’s hard because everything’s been done. I didn’t want to make fun of his weight or his appearance or all the other normal jokes. I thought what was the one thing that would really bother him – and I think it’s talking about his money and how little he has. It’s always a fun thing to try to push someone’s button. 

Were you concerned in the massive aftermath that this was going to be what you were going to be known for and asked about forever, or was it an honor, a pin always in the lapel?

In the aftermath, the thing that really got to me was how supportive all the other comics were. Because really all I think anyone wants in their career is the respect of their peers, and to have comics come out and support me and have my back, it was great. To have people like Dave Chappelle and Letterman and Seth Meyers and Stephen Colbert and all the late night shows to come out and have my back, that made me feel really good.

You moved from that onto "The Break." What was working with Netflix like? We know so much and so little about their inner workings; we know about the algorithm but we don’t know about control or viewership. What was your experience like?

My experience was that they really, really care about the algorithm. (laughs) I don’t really think they’re quite equipped to do a topical show yet. And I think they know that. It’s really just about making changes within their platform if they ever want a show like that to work. Even Norm’s show that’s on now, those are all pre-taped interviews that can really played at any time. They’ve never been able to do a topical weekly show – and the platform isn’t set up for it. And until they’re willing to make those platform changes and those interface changes, I don’t know how they’ll be able to make it work.

Was there anything you were really looking forward to doing or changing for a potential second season?

When we got the initial series order, it was only for ten episodes. So we knew we only have 10 episodes to kind of try to make a statement – which is really hard to do for a late night show. I worked at Seth Meyers at the beginning, and it maybe took us a year and a half to two years to figure out what the show was. So to do that in 10 episodes, it was never going to be enough.

I do think in episodes eight through 10, we really got our teeth into something. We really got into what I initially wanted to do, which was to take a break from everything – enough talking about Trump and the administration and all that nonsense that we hear over and over again from everybody. Some of my favorite things we did was "Sincere and Angry," where we made fun of satire comedy and what it’s become. And I’ll always be happy that, in our 10th episode, we ended on a double monologue where the second part talked about crows having sex with dead crows – which is a real thing happening in the world right now – for eight minutes. (laughs) I’m sure there was plenty of other political Trump news to talk about that week, but it was fun and silly and what I really wanted the show to be. So I’m thrilled that’s how we ended. (laughs)

In between all of these comedy breakthroughs, you also ran a 50-mile ultra-marathon. How do you get through something like that?

It was definitely more mental than it was physical. I mean, it’s also very physical. I trained for a while leading up to it, although because I was so busy, my training got cut down to maybe two days a week. So I would run 20 miles one day, then 10 to 15 the next, just trying to squeeze in as many miles as possible and get my body ready for that amount of mileage in a short period of time.

I have to say: Running it was great up until about the 32nd mile. From miles 32 to 42, I was positive I was going to die. (laughs) And then around mile 43, I was like, "Alright, seven miles left, we can do this," and I was focused on finishing. The crazy thing about races is that you feel very accomplished when you’re doing it – and then you see how many people ran it faster than you and how much faster they ran it, and you’re like, "Oh, I’m nothing." It’s a huge boost of confidence and morale and, at the same time, soul-crushing. It’s a great metaphor for life! (laughs)

And now you’ve got another comedy special in the works?

I’m working on a new hour. It’s still getting into shape; that’s why I’m going on the road, because there’s no better place to button up an hour than to tour all over the country. Hopefully within the next six-ish months, I’ll have a new special taped. Can’t say where it will be yet, but I’m really, really excited about it. I didn’t want to do another special until I had something that was better than my first one, and I do think I’m now on the road to that. So it’s really exciting, and I love the jokes that I’m working on and the overall arch of the hour. 

And I’m excited for people to see it. That’s why I love going on the road. I live in New York; I could do these jokes in New York every night. But you have to do them everywhere in America – and Canada and Europe – because you don’t just want them to work in New York. You want them to work in Milwaukee or Albany or Knoxville. You want them to work everywhere. That’s part of the joy of being on the road. It’s like, "I don’t know, let’s see!"