The Chicago Cubs have been called all kinds of names over the years, but “blockheads” is the one Thom Lessner has taken to heart. A self-taught artist, Lessner paints portraits of Cubs players on wooden blocks. His style is bold, cartoonish; sometimes his pictures look like the players, while other times they bear only a mild resemblance. Is that Willie Hernandez or Jose Cardenal? Only in Lessner’s world does Don Kessinger look like Don Zimmer–that’s part of the charm.

Lessner, 24, was born in Evanston. These days he lives on the west side of Philadelphia with his sister, Bridget, and her husband, David. But he doesn’t paint Philadelphia Phillies or Pittsburgh Pirates–only the Cubs capture the innocence of his youth.

“There’s a big sentimental aspect to it for me,” Lessner says. “They look sort of childish to begin with, and I feel like a kid thinking about it. I played baseball until eighth grade, but between the coaches and the baseball strike I started hating it. I got more into music and skateboarding. After the [Sosa-McGwire] home run chase of ’98, I got back into baseball.”

In 1996 he started painting, doing portraits of his favorite musicians–the Ramones, Jonathan Richman–before starting the baseball series. Mostly using acrylic house paint, he works on blocks that range from two and a half inches square to three feet square. Prices range from $10 to $100.

He uses plywood and two-by-fours he finds in the trash–“I don’t have a lot of money, I don’t make a lot of money.” It takes him a couple of hours to do a modest-sized block. All of his portraits are one of a kind. The thread that connects them can be seen in their beady eyes: appropriately, most of Lessner’s Cubs look shell-shocked.

“Actually, I start with the eyes or the nose,” he says. “Then I do skin color and background. It tends to get exaggerated….I’m not trying to make them identical to the players, so the funnier ones sell best. Like Bill Buckner.” Buckner, who played for the Cubs between 1977 and 1984, sealed his legacy as a member of the Boston Red Sox: during the 1986 World Series, a ground ball went through his legs in the tenth inning of game six, helping cost the Red Sox the series. One of Lessner’s pieces portrays a detached Buckner, sighing, and the words “I should have never left Chicago.” A newer piece depicts him weeping.

“Buckner just looks like a baseball player,” Lessner says. “He’s fun to paint. He’s got the big mustache. He looks tough. I’d rather paint Rod Beck [now a Red Sox reliever] or someone with big features than a star player. I like people with character in their faces. Sosa is difficult for me. I’ve come close, but haven’t really hit it yet.”

He’s not a statistics freak, but if a Cub performs poorly, chances are Lessner won’t paint him. “I saw a few games with [deposed 2001 opening-day center fielder] Damon Buford. He didn’t do anything for me. I wouldn’t do [ex-third baseman] Willie Greene. I like [pitchers] Jon Lieber and Kevin Tapani, but they’re not real exciting looking. So I don’t think I could do much for them.”

Lessner is a cook at Jill’s Diner in Philly’s Reading Terminal Market, and he finds parallels between cooking and painting. “I cook a lot of soups, stir-fry, stuff that is thrown together but stuff you can always fix. I don’t bake. And I don’t do real intricate paintings. With my paintings, I can go back and touch them up or do an outline if I need to.”

He’s becoming a hot prospect in the Philadelphia art community; his portraits have shown at the Spector Gallery, Space 1026, and 1 Pixel. He made his Chicago debut in February at the annual Cubs Convention at the Chicago Hilton & Towers, where he sold more than 40 pieces. And last Saturday he had a booth at Collect-O-Rama, an art fair organized by Intuit: The Center for Intuitive and Outsider Art.

This Friday and Saturday around Wrigley Field, Lessner will be selling nearly 170 blockhead portraits, plus a few painted on baseballs. He won’t be selling from a booth. “I’m going to visit my Grandma Marge in Arlington Heights and see if there’s a shopping cart I can borrow out there,” he says.

Lessner also plays guitar and sings. He collaborated with Chicago singer-songwriter Peggy Honeywell on her upcoming CD Honey for Dinner (on Galaxia). This winter Honeywell and Lessner toured Japan. Lessner played guitar and sang backing vocals, but sometimes he writes his own songs. And he’s written a poem about Andre Dawson: “Andre, Andre, Andre Dawson / You got big teeth so don’t forget to floss ’em / They called you the ‘Hawk’ cause you look tough and serious / You probably drive a truck with a bumper sticker that says: ‘FEAR THIS.'”

“My best songs are goofy little rhymes about a situation, sort of like the Dawson poem,” he says. “They tell stories.” In Lessner’s world, every picture tells a story, even if every Cubs fan knows how it’s going to end.

Art accompanying story in printed newspaper (not available in this archive): photos/Jon Randolph.