If you’ve attended an event hosted by Milwaukee Film, there’s close to a 100% chance you’ve run into or at least seen Kristopher Pollard. I have run into him on and off over the years, and have always meant to sit down and have a chat with the man who, as membership director, has grown the organization from the 400 or so members they had when he started to nearly 5,200.

It’s quite an impressive feat, and a testament to his dedication. But it’s also a great indicator of the positive shift in creative culture in Milwaukee over the last decade.

I hadn’t seen Kristopher in a while and on a random Saturday in April noticed that an event called Milwaukee Zine Fest was happening at the public library downtown. I was intrigued, especially as someone involved in a digital “zine” of my own. (And hey, we’re always looking for new contributors). As I walked past the stapled together narratives and homemade illustrated tomes I looked up and saw Kristopher sitting behind a table. It was unexpected, certainly, and after a cordial greeting I looked down and saw his work neatly situated on the table in front of me.

What I saw grabbed me immediately. Simple, yet sophisticated drawings of characters, drawn with what looked like a fine point. They were quirky, tongue in cheek, sometimes off color depictions culled from Kristopher’s strange-view-of-the-world brain. There was a discernible style and quirky quality to the work. And like Kristopher, a sense of humor was apparent in every pencil stroke. It’s not surprising that someone involved in Milwaukee Film would make art that is, dare I say, entertaining.

As we talked I realized nearly immediately that the narrative got much more interesting.

We finally sat down for that chat at the café at No Studios, the Milwaukee Film office’s new home. Kristopher has a jovial, relaxed, warm and inviting way about him, and you can instantly see how he could likely convince anyone to join Milwaukee Film. But you can also detect a quality in him that is important to have for any artist or membership director: Patience.

“I’m not really a spontaneous person,” he told me, speaking about the moment 17 years ago when he decided in a spur of the moment to move to Milwaukee. He was helping some friends move and fell in love with the city immediately. For two years after that he worked at the now sadly defunct Schwartz Books and then had a 7-year run at Lubavitch of Wisconsin.

But it was an opportunity to illustrate a movie poster for the winner of a short film contest for Milwaukee Film that got him his first exposure to the organization he would end up working for. “I did a poster for an old program Milwaukee Film had where they had students created short films – I did a poster for a film – got paid and got a bunch of free tickets,” he remembered. “My illustration was tied to Milwaukee Film – then a friend said the job was coming up and it turned out really well.”

His work caught the tasteful and artistic gaze of documentary film company The September Club, and he has since created alternative posters for nearly all of their films, including Jim & Andy, The Blood is at the Doorstep, Rock the Bells, and Collapse. The gig has really helped him hone his graphic design craft.

He may not have discovered his ability to illustrate it if hadn’t been for a friend’s regular Wednesday night get-together called “The Wednesday Night Drawing Auxiliary.” Kristopher was into making collages at the time, and he remembers it as a very formative period in his life. “We didn’t collaborate – we just had a set time to work on stuff – but one time I didn’t have my collage stuff with me so I started doodling and drawing. I remember (my friend) had really nice pens – so when I was drawing I thought it already looks better with different gauges and then I got more interested in it.”

That interest in drawing has now become an ambitious side hustle and Kristopher has set his eyes on creating books complete with characters, storylines, and his trademark sense of humor.

That sense of humor is palpable in Kristopher’s latest work where he is drawing – of all things – people’s butts. “I have friends pose and I dress them up – it’s very highbrow. I draw portraits of my friends in these lofty poses, with costumes and stuff,” he told me. “Then separately I do a portrait just of their ass – they get to decide how their butts look. They can be naked or not – whatever they want – and I put this ornate background on it – I would love to print it very seriously – like have hard cover with embossed type – make a ridiculous subject very seriously – very ornate.”

Kristopher’s “pre-butts” work includes two other books; one is a collaboration about buffets called Buffet Life which had, in his words, “ridiculous collages about food based things.” He and his collaborators wrote haikus about buffets, included a fake history of the buffet – and even created the characters Warren and Jimmy Buffet dubbing them “The Buffet Brothers.”

Kristopher’s other book depicts fictional rappers complete with sample lyrics, called Fake Ass Rappers. In it he introduces is to Sha-Shaun Shaun, Dr. Pricey Shoes, Sloppy Jonze and Gold Felice, whose signature rap is: “Rhymes so contagious I can make the world itch/You can’t even speak, irregardless ain’t a word bitch.”

For Kristopher, he has a fascination with, of all things, the lottery.

“I know the lottery is ridiculous but once in a while I do it for fun – you either stay the course or become a millionaire. The lottery ticket is fascinating – you’re paying a dollar for one second of hope – if you lose the lottery it just means someone else wanted it more.”

Follow Kristopher on Instagram here.

Kristopher's Etsy store is here.

You can become a member of Milwaukee Film here.