Dent May offers kitschy but serious fun with a ukulele

The joke is always funnier when the joker doesn't know he's joking. Like the comedian who struts onstage unaware of the toilet paper stuck to his shoe.

The musical equivalent is Dent May, who plays the ukulele and sings with an affected warble most often associated with entertainers from the golden age of velvety cocktail lounges and dashingly rumpled evening wear. His debut, titled "The Good Feeling Music of Dent May and his Magnificent Ukulele," was released earlier this month on Animal Collective's Paw Tracks label.

Song after song is anachronism — sonically sugary as a Four Freshmen hit, emotionally ambivalent as a Don DeLillo novel. With the same aplomb May extols the imagined wonders of Paris ("pretty girls in black berets reading books in sad cafes"), he unleashes scorn upon an underachieving post-grad ("college town boy / get off your ass and do something"), both songs backed by the same jaunty ukulele, jangly tambourine and doo-wop chorus. He swoons from the romantic magnetism of a PowerPoint presentation in "At the Academic Conference" and, two tracks later, proclaims unabashedly, "I'm an Alcoholic." May's ambiguity is confusing and vicious, and in an uneasy way, hilarious.

This is clearly some sort of meta-pop quip. May — a 23-year-old Mississippi native who favors Coke-bottle glasses and (surprise!) dashingly rumpled evening wear — must be attempting a clever ruse. This national tour — his first — is an extended situationist experiment wherein he will bully the audience with his innocence. He will sing "I'm an Alcoholic" to crowds that may contain an actual alcoholic; he will play "College Town Boy" in actual college towns populated by actual college town boys. His literalness is ironic. His nebbishness is a provocation. He will wield this petulance like a rapier, needling through audience expectations to bleed out all our bad habits and shortcomings.

On his cell near his home of Taylor, Miss., May — his first name, Dent, is a family name that his dad shares — extends no insight into the music's latent irony or humor or meaning. Either he's ignorant of the toilet paper stuck to his shoe or he stepped in it intentionally and is feigning ignorance because it's funnier that way.

Point blank then, Dent: Is this music made with a straight face or are you just fooling?

"I see what you're saying," he offers. "I'd say it's with a straight face and I'm definitely serious about it. But I guess on purpose I like to ride the line between funny sad, ... to make pop music that's a little more uncomfortable to people ... . I like kitschy kinda stuff — John Waters and a lot of stuff that's so bad it's good in a way. Choosing the name alone — Dent May and his Magnificent Ukulele — it's almost inviting people to write you off as soon as they hear it. But I guess that's kind of why I like it."

DM&HMU played their first show only a year ago. Before that, May played in a power-pop band and a country-western band and occasional solo ukulele. He's currently working on a psychedelic-country-rock opera called "Cowboy Maloney's Electric City" (the name's taken from a chain of Mississippi-based appliance stores) as well as electronic dance music under the moniker Dent Sweat. There is clearly more to May than His Magnificent Ukulele, though the persona and its intellectual baggage might swallow him.

"Ultimately I think I'm a fan of pop of all eras," he says. "I also love '80s and '70s pop and rap music and stuff. Eventually I wanna bring that all to the table and stuff. I'm kind of just exploring right now."

Dent May opens for AC Newman (featuring Carl Newman of the New Pornographers) at Neumo's at 8 p.m. Saturday; 21 and up; $13 (advance at www.ticketswest.com).

More must-see shows this week:

Sunday

Formerly a trio, now a quartet, Jacob Fred Jazz Odyssey spectacularly trample the line between jazz and rock (9 p.m. Sunday at the Tractor Tavern; $10).

Tuesday

Baltimore's Thank You bill themselves as an "athletic rhythm/action unit," which is pretty spot on (with Mi Ami at Vera Project at 7:30 p.m. Tuesday; $5).

Jonathan Zwickel: zwickelicious@gmail.com