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Pleasant's albums, however, could go in the folk section; after all, Pleasant does possess some of the characteristics--and a healthy portion of the style--traditionally associated with the genre: acoustically based songs, an occasional political observation, and a thoroughly useless college degree (in political science). But despite the expanding definition of modern folk--aided by the presence of newcomers like Jewel and Ani DiFranco--the label doesn't quite stick with Wally.
Pleasant's albums also could be filed under comedy. With songs like "The Day Ted Nugent Killed All the Animals" ("Bob Barker cried/Ricki Lake tried/to save 'em"), Pleasant has the same quirky sensibility as Bruce McCulloch (from the comedy troupe The Kids In The Hall, whose similar album of songs and sketches is considered comedy), and the same knack for finding the humor in the day-to-everyday as Jerry Seinfeld. Lumping Pleasant in with Gallagher and Sinbad, though, makes Pleasant seem like a sort of less retarded Adam Sandler--a guy who could write "Red Jacket," only with more verses.
There's more to him than that, but even Pleasant doesn't know where he fits in. "I just try to sing about things that people may not have thought of much, things that happen that people don't stop to think about," he says. "I deal with some of the same things that comedians do, talking about life in a funny way."
The most logical place for Pleasant is where comedy and music intersect, the region occupied by such hybrid groups as They Might Be Giants, but without quite as much weirdness. Pleasant won't tell you that the statue got him high, but he knows the outrage that the holder of a parking ticket feels ("With the crime rate so high, and people's hope at a minimal/they'd rather ticket me than arrest a real criminal," from "I Hate Cops"). It takes more, however, than a keen eye for human foibles to gain the kind of following Pleasant enjoys; he's just as likely to see the crock at the core of his own act as anybody else's. His first album, Songs About Stuff, contains the hilarious "Bad Haircut" ("I looked in the mirror and almost fainted/My head looked like something Picasso painted"), and Pleasant himself appears on the back cover with a titanically bad haircut and a look on his face that tells you he knows just how ridiculous he looks. This ability to laugh at himself as readily as at others is why he has obsessive pockets of fans throughout the country, writeups in Billboard, CMJ, and The Wall Street Journal, and three World Wide Web sites devoted to his exploits, while Roger Waters is still remembered as that asshole from Pink Floyd.
Pleasant truly lives up to his name, genuinely glad you called and happy to talk to you from his house in East Lansing, Michigan. Just like his audience, he values human connection.
Once not too long ago, Pleasant did a guest appearance at local station KDGE-FM 94.5. It was pouring rain, and one of the interns at the station couldn't get his car to start; Pleasant left the studio and gave the intern a jump. After the intern drove away, Pleasant ended up getting locked out of the studio in the rain for a very, very long time. He still sends postcards to the guy he helped and whom he now addresses by the nickname Jumper Cables. Everybody knows--or has known--someone just like him: the boy next door who mothers implored their daughters to go out with, the quiet kid in the back of history class muttering sarcastically, or the been-there, done-that college senior dispensing sage advice to a confused freshman.
Pleasant has been all of those things. He grew up in Detroit influenced more by the abrasive guitar sounds of British punk bands than the sweet Motown soul the city is famous for. "In high school I listened to bands like the Who, the Clash, and the Sex Pistols--a lot of bands that smashed stuff," he says. "Me and my friends were mainly into smashing things. It's hard for me to listen to the old tapes we made of ourselves, because we would play a song and then smash all of our stuff."
By the time Pleasant moved to East Lansing to attend Michigan State University in the late 1980s, he had moved away from his early punk leanings and begun perfecting his pseudofolk sound at local open-mike nights and smashing the serious folk-singer archetype instead of his guitar.