Kelsey Cook has already had the opportunity to step on the legendary stage at The Wilbur in the past. But this time around, things are a bit different, the stakes are a bit higher, and Cook is firing on all cylinders as she prepares to take on the headlining spotlight.
Making her way to the Theatre District tonight (February 21) as part of her Happy Hour tour, the Minnesota-based comedian can’t help but feel excited and proud of the work she’s put in to get to this point in her career, and as she builds on the momentum of releasing her new special Mark Your Territory, as well as the familiarity from her chance to open for Jim Norton at The Wilbur in 2016, she already knows what it takes to control the room – but to get the chance to headline is still a dream come true.
“There’s a level of pressure with either situation, where opening for someone is where you want to make sure you’re doing your job and setting them up for as much success as possible, but there’s something extra special about headlining because it’s your crowd,” Cook tells Vanyaland. “So there’s a bit more of a built in confidence in the sense that people came to see me. To have the chance to be at The Wilbur, and have it be my crowd is just really cool.”
While it’s tough to compare two separate bodies of work, Cook still very much feels the palpable creative and personal growth that has transpired in her life since the release of her debut special, The Hustler in 2023. Naturally, as an artist who is willing to be open with audience, the experiences that have led to that growth have found their way into her new hour, and she looking forward to not only seeing how it rolls out in front of a Boston crowd, but also how can she bring the light out of the darkness in this new “era” of her career.
“I’ve had some things happen in the last year that have become part of the material in a more natural way. I stopped drinking last year, so I talk about being sober, being diagnosed with depression, and I go a little bit into my mom’s dementia,” says Cooks. ”I don’t go into it as much as I did in ‘Mark Your Territory,’ but those themes are all sort of connected here, and I’m just trying to find the silver linings in all of it and bring humor to it.”
While her stage presence has naturally evolved over time, Cook has also taken some personal struggles head on, particularly when it comes to alcohol, and as she closes in on a year of sobriety, she’s feeling a clarity both physically and mentally that have only added to her ability to grow as an artist.
Cook has been especially appreciative of that clarity as the time between the recording her latest special and the start of her current tour allowed for constant growth and agility in her jokewriting process, which has only enhanced the experience of her audience being able to see all new material so close to the release of her latest hour.
“I feel really fortunate because ‘The Hustler’ was received so well, and that helped my ticket sales boom, so I was touring so much and got right to work on the next thing, and was able to turn around a lot of new material and get it to a good place,” says Cook. “It was also exciting to have this new, added fanbase for me to work the ‘Mark Your Territory’ material out to. That hour really gave me more confidence, and permission to just be myself and talk about the things I really wanted to talk about.”
Of course, Cook’s main objective every time she hits the stage is make sure that everyone has the chance to laugh, let loose, and enjoy the moment. That objective will remain the same when she’s on the Wilbur stage too, but she’s also hoping that those that feel a connection to some of her more personal material go home with some validation at the end of the night.
“Opening up and talking about depression, especially, it’s been cool to have people come up to me after shows and thanking me for talking about my struggles with it, and anti-depressants, intrusive thoughts, and all of that,” says Cook. “It’s definitely not as taboo of a topic as it used to be, but I do hope that, for anyone dealing with any of those issues, they can walk away feeling seen.”
KELSEY COOK :: Friday, February 21 at The Wilbur Theatre, 246 Tremont St. in Boston, MA :: 6:30 p.m., $38 to $48 :: Advance tickets