From the inscrutable imagination of Kristoffer Puddicombe comes a spanking new Milwaukee show that includes comedy, music and quizzes involving live audience participation.
I Should Know This – 8 p.m., Friday, Aug. 14
Inspired in part by NPR’s “Wait Wait…Don’t Tell Me!” and the one-two punch of music and comedy performed way back when by Willy Porter and The Dead Alewives, Puddicombe and James Boland have brainstormed what Puddicombe says he hopes will become a monthly game show.
“For a while, a year or two maybe, I had been thinking that when I go to see live music, I wanted more comedy and that when I saw a comedy show, I wanted the energy that live music gives,” Puddicombe says. “James had been watching old YouTube episodes of a quiz show in Britain that used panels of comics and celebrities. We kind of fell in love with the idea and merged both.”
Both Milwaukee school teachers, Puddicombe and Boland used their winter breaks to compose the format for “I Should Know This.” Puddicombe will be the host, with a panel of local comedians including:
- Boland
- Lee Rowley
- Jared Stepp and
- Vince Figueroa
“Lee, Vince, James, and Jared have been great help, and I think they will be the core,” Puddicombe says, “but there are so many hilarious folks that we’d love to get on stage that I imagine there will be various folks doing it. That’s one of the beauties of the show. It’s not that dependent on any one of us.”
As for the music, Puddicombe plans to install Milwaukee singer/songwriter Hayward Williams as a somewhat regular musical guest, but Williams wasn’t available Aug. 14.
“Brian Bayer, who is super awesome, agreed to play this show,” Puddicombe says. “I think this too will be a rotating cast. I like the idea of bringing in different music because you potentially get different draws from their fanbase who likely wouldn’t come to see a show like this. I think this may help to grow the show in an interesting way.”
The inaugural “I Should Know This” – at ComedySportz, 420 S. 1st St. – is pay-what-you-can.
“It’s our first go round, and we will be working out some kinks,” he says. “I think the show depends heavily on audience interaction, and rehearsing it is weird that way, so I think we are looking to see what kind of energy that gives the show and then how we can direct and maximize that going forward.
“There are a fair amount of moving pieces to the quiz rounds etc., so we hope to get a sense for how well those will work, and how/if we need to tweak them to make them more seamless.”

