Once more ‘round Pleasantville

“I guess like anybody else, I just enjoy comedy.”

Comedic singer-songwriter Wally Pleasant is gearing up for a return to the stage and studio. Following two shows this weekend at the Windwalker Underground Gallery in Charlotte, likely his only performances of 2018, he’ll be joined by a stable of studio musicians for his first fully realized project in 14 years, “Happy Hour.”

Pleasant in 2018 promises a musical affair rooted in late ‘60s country music, his latest obsession. Think Waylon Jennings and Guy Clark.

“About five years ago, I got really into a very specific era of country music, late ‘60s, early ‘70s stuff. I like the way it’s produced, and I like the songwriting,” Pleasant explained while sipping a Coke at a Charlotte pizzeria. “I started writing those kind of songs, and I already have two albums worth of them. I wanted to hear how they’d sound recorded properly in a studio.”

At the helm will sit renowned Michigan music producer Jim Diamond — best known for his work on the first two White Stripes albums.

“I’ve sent him 15 demos. He’s gonna get some really great musicians, and I’m basically gonna karaoke over the songs I’ve already written,” Pleasant said.

“Mid-Michigan has really great musicians. We’re talking about having Drew Howard and Mike Lynch, we’re lucky to have those resources here.”

Pleasant’s music has evolved beyond just him and an acoustic guitar, but his playfully sardonic sense of humor and sarcastic wit haven’t gone anywhere.

One song from “Happy Hour” parodies Jimmie Rodgers’ “I’m Free (From the Chain Gang Now)” with a story of Pleasant feeling “free again” after losing his cellphone.

Another song details a painful breakup, but, does so with a series of math puns. It makes one chuckle and then immediately feel kind of sad about doing so.

Diamond worked on albums with Pleasant twice before, playing guitar on 1993’s “Welcome to Pleasantville” and 2002’s “Hoedown.”

The two will settle into the studio, upon Diamond’s return from a trip to France. “ He’s really into that garage-y surf rock sound with Mosrite guitars,” Pleasant said. “He’s done a lot of great stuff.”

Joining Pleasant onstage in Charlotte will be old friend Brian Hefferan and Pleasant’s son Stanley Bullard, who will open the show with his piano playing.

When Pleasant became a college rock sensation in the early ‘90s, he was somewhat of an anomaly. While independent rock, or college rock’s rejection of mainstream clichés, was refreshing at the time, it often bordered on pretentious navel-gazing. And then you had Pleasant, singing about Ted Nugent killing all of the world’s animals. Nugent would later tell Pleasant it would only take a day and a half.

“There was an element of funniness in punk rock songs, like the Anti-Nowhere League’s ‘Woman’” Pleasant said. “I really liked that stuff, and it was during a time when acoustic music was very serious. It was nice to kind of make fun of that with such non-specific topics.”

The strongest proponent of Pleasant’s music, initially, was himself. He would bring his guitar to open mic nights in East Lansing, after frantically writing the songs earlier that same week.

After donning the Pleasant moniker — his real name is Wally Bullard — he attracted the attention of Michigan State University’s newly formed WDBM Impact FM radio station.

“I played their first-year birthday party and they made recordings of my songs,” Pleasant said. “They actually started playing them, so I thought, ‘I should release something eventually.’” He just needed the money.

How he found the funds for his debut album is just as unorthodox as his lyrics.

As a social worker in Ann Arbor, Pleasant hurt himself during a basketball game with the troubled teens he looked after. He quit that job shortly after, without thinking much of it, until he received a large compensation check via an insurance company.

“I got a big check, and that paid for the CD,” Pleasant laughed. “Tom Frey at Impact had the listings for all the college radio stations around the country, and I sent it everywhere. I started playing shows wherever they played my music. It was real DIY.”

Upon its release by Miranda Records, “Songs About Stuff ” at one point sat positioned above the likes of Blind Melon and NOFX on College Music Journal’s sound scan chart — the de facto Billboard for independent music.

Considering that the songs resonated with many young people, primarily due to the reliability of Pleasant’s lyrics, its not hard to liken the success of “Songs About Stuff ’ as a prototype for going viral.

“There are so many people discussing personal issues and doing songs, I could’ve not stuck out at all, or maybe I would’ve gotten really into it and done a YouTube channel,” Pleasant, now 50, said. “I suppose even though I’m an older dude I still could. It’s never too late.”

“Windwalker Presents Wally Pleasant” Windwalker Underground Gallery 125 Cochran Ave., Charlotte $10 Saturday March 10 (Sold Out), Sunday March 11 8 p.m. Saturday, 2 p.m. Sunday www.windwalkerunderground.com