It’s the holiday season in Boston, and as someone who is a big fan of snowy cities during the holidays, Taylor Tomlinson is excited to be making her way back, smack dab in the middle of it all. However, it’s far from the only thing she’s pumped for upon her return.
Not only will a five-show run at The Wilbur, which begins on December 14, mark her first time gracing the legendary venue’s stage, but she’s also designated this stop on her Deal With It Tour as the location of her next special taping. While the surrounding elements have Tomlinson ready to roll on Tremont Street, she’s also looking forward to showcasing the tools and creative muscles she’s acquired over nearly two years of working out the new batch of material, as she prepares to do what she’s always done best — look inward.
Brandishing what she considers to be something of an evolved level of maturity as a performer honed since her last special, Quarter–Life Crisis, Tomlinson is ready to cement her legacy in Boston by delving into her own experiences, failures, and trauma, as well as her struggles with mental health and everything that comes with it to deliver her most personal hour to date.
Vanyaland had a chance to catch up with Tomlinson ahead of her trek to the commonwealth, where we took a deeper look at getting back to “normal,” the comedic intellect and awareness of Gen Z, as well as what makes these shows, and this new hour, so special.
Check it out.
Jason Greenough: Starting off, you’ve been out on the road for a majority of the year. How have you been holding up as you start to see a return to some semblance of normalcy in that regard?
Taylor Tomlinson: It’s amazing. It’s so crazy to me that we were grounded for so long, and that we just weren’t on the road at all for the better part of a year. To finally be back in the swing of things, you almost go back at it too hard and push yourself harder than did before the pandemic, so the real challenge is dialing it back a little and finding that balance again and figuring what is a good amount of time at home and a good amount of time on the road. That was a struggle for a lot of us workaholics before the pandemic, and then the pandemic forced us to stay home and reignited any fears we had of the idea that if we stopped, that it would all just go away.
You were doing a lot of outdoor shows last year, like the drive-in tour with Whitney Cummings, and a lot of other comics had gone the same route. How does it feel getting back into a theater setting, as opposed to an outdoor parking lot or movie theatre setting?
It’s been amazing. I mean we were only doing the outdoor shows because we had no other options. Nobody was doing that because we always wanted to try performing in a parking lot. It was just truly the only thing to do, so to be back in a place where we don’t have to do that feels very luxurious, even with people wearing masks during the show. We’re just so grateful for it.
So how does that affect your approach to this hour, taking it indoors now after performing it last year in a different environment, getting used to the road schedule again and bringing it back into a familiar setting like a theater?
Well, when we were doing outdoor shows, we were just trying to remember how to do stand-up all over again. So, there wasn’t a feeling of getting this hour ready to be filmed so much as it was about getting the hour to a place where people won’t be mad that they paid money to see it. Once it was there though, it felt good, but once we got back into comedy clubs, that was when it really started feeling better, because doing the outdoors wasn’t consistent. It wasn’t every weekend that you were out, but instead you’d do ten shows outside, start to think you have it back, then have a month or two off.
So, now that brings us to this string of shows you have coming up in Boston at The Wilbur. Most of them are sold out, and they sold out fairly quickly. How are you feeling about coming back to the city for your first time at The Wilbur to tackle this comedy landmark?
It’s definitely intimidating, but I’m also just grateful that I get to do it. I don’t think I’ve ever headlined in Boston, or not that I can remember, at least. I don’t think I’ve ever done a weekend of shows or anything like that. Just a few one-nighters, but obviously I’ve heard so many great things about The Wilbur, and so many great specials have been filmed there. It’s just so iconic, and I feel really lucky that we sold so many shows, so now I have three dry runs, I guess, before we film the special there, because you don’t really ever get that.
With that, what was the driving force to choose Boston to shoot this special?
Everything we said, and the fact that we have so many shows there. And where it is a place where so many people have filmed specials, there is something to be said for that because in a theatre that has had that experience, you just don’t know what to expect, but it’s also just one of the best comedy cities, and we knew we could get the best crew on it. All of that came into play, and obviously, Boston crowds are amazing.
What’s been your favorite aspect of bringing this hour around the country and getting it special-ready?
This is such a personal hour for me, and there’s a lot of topics that I hadn’t talked about yet, because I didn’t have the maturity as a performer to talk about them. With Quarter-Life Crisis doing as well as it did, I feel like I’m able to bench out more into those topics that I wanted to do for so long. I hope people like it, and the response so far has been really nice, and it’s also been crazy to see the change to look back at my career before that special came out, which was also right before the pandemic, to looking at it now and seeing how much of a different career I have now.
I wasn’t able to be on the road while people were watching that special, so it wasn’t gradual at all. You’re maybe selling out one show for a whole weekend, then you’re stuck inside for eight months, and then you’re all of a sudden selling full weekends. It all felt very sudden, because you just don’t know if people are going to remember what they watched during the pandemic.
On your social media, you’ve been very vocal about your struggles with mental health, especially during the pandemic. Now that we’re coming out of that part of things, a lot of people are not necessarily looking for soldiers in the same fight, but it feels good to be able to gravitate towards someone who is talking about the same things that we were all thinking about during those times. Was that part of the driving force to delve into those topics? Not necessarily in the sense of helping to make people feel better about their own struggles, but just from your perspective, to feel more comfortable diving deeper into those topics?
It’s honestly more of the fact that I write from my own experiences, and that was what was going on with me. My mental health was probably at an all-time low right before I filmed Quarter-Life Crisis, and my career was going better than it ever had before, and I was still struggling more than I ever had. A lot of what was going on right before that is in this hour, and the pandemic hit, and there wasn’t much else to do but to pivot and do content online, and for me, it was just about being honest about what was going on. I mean, nobody was going out and posting hot hiking photos. Everyone was inside, and sad and scared, and so it just felt weird not to talk about how it felt, and selfishly, it made me feel better to hear people say they were dealing with the same stuff.
I didn’t worry necessarily, but I did wonder about coming out of a pandemic, or at least the worst part of a pandemic, if people would rather just want silly stuff, instead of talking about the news or mental health or anything darker. I’m sure some people feel that way, but I do think some people experienced anxiety and depression that they hadn’t ever experienced during the pandemic. I think Gen Z is very self-aware on that front, and people got very informed as a result of that, and not watching the news actually made you much more aware of what was going on in the world, myself included.
So, it really wound up being the opposite of what I thought, initially, where I was thinking nobody would want to talk about anything real or serious. I actually think people are really wanting that.
Absolutely. Delivering that kind of thing from a comedic standpoint is the sugar that helps get the medicine down. I think that’s very therapeutic, or cathartic in a lot of ways. Now, obviously it isn’t necessarily easy to deliver a message like this in a comedic context, but was it tough for you to figure out exactly what to talk about on that front and find a solid foundation for it?
No, because I had all the stuff I wanted to talk about and it just really solidified during the pandemic, because you just had so much time with yourself. Ugh. You had to really deal with your own shit, and there was no getting away from it. That definitely played a role, but I don’t have any pandemic jokes. I think we made all those jokes while things were happening, and we were all making pandemic content every day.
All I know how to do is write about what I’ve experienced. I’m not a political comedian, nor am I someone who is good at that. I only know what I have, and hopefully it’s relatable to other people. That being said, I’ve come to realize that this hour is very emotionally draining. Being on tour like this, it’s a very personal hour where I go over a lot of my failures and trauma, and it’s just tough. It’s stuff you talk about in therapy, and I think it’s funny and relatable, and I’m proud of it, but it’s not as easy as Quarter-Life Crisis was to do every night. And now, you’re also in theaters doing meet and greets and stuff, which is kind of like another show after the show.
Don’t get me wrong, I love meeting people, but you have to bring it at all times, but now everyone knows some really personal things about you. People will reference things and it makes you go ‘Who told you that? Oh wait, it was me.’
With this hour being draining and heavy in that sense, and going off of what you said about talking about it in therapy, would you say it’s been cathartic?
I think so, for sure. Like a lot of people, I got more into TikTok during the pandemic, and again, Gen Z is fucking hilarious. They have such a dark sense of humor because they’ve lived through some horrifying shit, so I do think my sense of humor has always been darker, but I was always worried about making people feel uncomfortable. The nice thing about having more of a fanbase or a following at this point is that you feel like you can go to those places now, and people will follow you there.
Right on. Like I said, I’m really excited to see this new hour. But now I’m down to my last question for you — beyond a comedic context, or coming to The Wilbur, what are you looking forward to most about this trip to Boston?
I do have a day off in the middle of the run, and I haven’t been to Boston in a few years. I’ve gotten a lot better with asking fans for recommendations when I’m in cities, and I usually only have a few hours to do one thing, so to be able to have a whole day there to actually see the city will be fun. I’m also really happy that it’s right before Christmas, because I love Christmas in a big snowy city.
TAYLOR TOMLINSON :: Tuesday, December 14 to Friday, December 17 at The Wilbur, 246 Tremont St. in Boston, MA :: $37 to $137 :: Wilbur event page and ticket links