Whenever Chris Fleming plans his annual return home with shows at The Wilbur, he often forgets how close he books them to the holidays, and just how likely an act of god is when it comes to the weather. But what he doesn’t forget is the love and support that’s waiting there for him, year after year.
It will be much if the same case in that regard when he makes his way to Tremont Street for two shows at The Wilbur on Saturday (December 17), as he makes his always-triumphant return to the Commonwealth with a brand new show that comes packed with virtually everything you could ask of an artist like Fleming, who leaves almost nothing off the table when it comes to what his show will entail. With the loosely gooses mentality still very much so the fuel for his ever-burning creative fire at the very base of it, Fleming is stoked to bring the new material to a hometown audience — even if the pressure is a bit higher than usual.
“The Wilbur is always so much fun to come back to,” Fleming tells Vanyaland. “It’s one of those things where most of my family comes to the show, so it’s the most exciting thing, but could also be the most devastating thing because if you bomb in front of your family, these are people you have to see for the rest of your life. Whereas if you eat it in Charlotte, you can just leave Charlotte. But it always feels like Boston wants me to do a really good job, almost like I’m performing in front of a bunch of teachers, which is kind of funny, because I did find out that my high school teachers do come to see me.”
Known for curating both wild and thought-provoking experiences with his stage shows, Fleming has been hard at work to put together a multi-layered show that balances the funny with existentialism, and in the case of this particular show, a fair amount of “violent acrobatics” and new music, as emphasized by Fleming, as well as a few heavier explorations along the way.
“The whole show sort of dances around identity and the confusion around my identity, and how I feel like the people who are familiar with me have a better sense of what’s going on with me sometimes,” says Fleming. “So there’s some dramaturgy around my background, as well as the concept of hell, with a little bit of Irish Catholicism and fear thrown in there too.”
Even after running the show for the better part of the last year, Fleming continues to add and subtract bits on a regular basis. But even with the “work in progress” feel, while he may not know exactly what will happen until he tries it out, and fully admits that he won’t have an ironclad rundown of this show at really any point, he knows that the Boston comedy crowd expects nothing but the best, and he’s fully determined to give it to them.
“I did a version of this show at Town Hall in New York back in September, which is a little bit bigger than The Wilbur, and for theaters like that, I feel a certain type of pressure to have my shit together more before going into it,” says Fleming. “But the laughs last for so much longer in a room of that size, so it’s the little rooms you have to worry about because you could do a joke, then run an errand and come back. But I’m definitely going to be feverishly scrawling down notes the morning of the Wilbur.”
The process in which the Stow native operates is not a common one, where the material that churns out of his brain is often the result of quickly jotted notes and a black and white “love or leave it” mentality that expels any need for trimming, which Fleming is quick point out as his least favorite thing about his line of work. He’s aware that people around him get freaked out by his approach, but he’s not worried about following the old school “Johnny Carson mentality” of holding a tight five close to the chest, but instead will continue to flow in the way that works for him.
“I’m really bad at reciting lines and material,” says Fleming. “I get this kind of beginner’s luck thing where I can try out a new concept on stage, and get a big laugh on it, but then I’ll try to recreate and I can’t even remember what was funny or interesting about it, so I love being in that beginner’s phase, and I really don’t like fine tuning.”
With every new show Fleming presents, there’s something else that’s more exciting and fresher about it than the last one. No two shows are alike, and Fleming has carved out a significant spot for himself in the comedy game with his virtually unparalleled ability to pull inspiration out of thin air and effectively destroy without much strain. But even as he brings another year’s worth of experience to a hometown crowd, he’s not resting too much on “showing off” how he’s grown. Following the teachings of Comedy Studio owner Rick Jenkins, and the elusive decibel levels of laughter reached by fellow Massachusetts comics Robby Roadsteamer and Bill Burr, he’s letting the material do the talking.
“One of the best things that Rick taught me was that it’s all about the material and that there really isn’t room for that kind of victory lap, because as soon as you start thinking about it, you let your guard down,” says Fleming. “I would be a much happier person if I didn’t think this way, but if there’s anything that i can really consider to be the most ‘Boston’ thing about comedy after doing it for so long in that city, is that there is always someone who can get louder laugh than you, and I’m a clown for the decibel. I have a decibel quota. So whenever I do come back, I’m acutely aware of it because it is such a great comedy city, and I feel like I just need to hit those highs that I remember so vividly seeing as a teenager.”
His year-end shows at The Wilbur have become just as much of a tradition for his fans as a trip to Kung Fu Tea before he hits the stage has become for him, and although Fleming is looking forward to delivering his latest tapestry of oddity and surprise, he’s got some other plans in mind for his year’s-end trip back home.
“I love being able to see my family whenever I come home, so I look forward to seeing them after the shows are over, and I always enjoy going to Veggie Galaxy when I’m back in town,” says Fleming. “I love doing shit like that. I also look forward to roaming around Davis Square with my sister and maybe going to The Buffalo Exchange.”
CHRIS FLEMING :: Saturday, December 17 at The Wilbur Theatre, 246 Tremont St. in Boston, MA :: 7 & 9:45 p.m. :: Tickets are $38 to $47