Don Lennon reclines diagonally in a booth at the Middle East restaurant. He turns and coughs, takes a weary pull from his Guinness, then speaks sotto voce, hardly audible over the clamorous blare of Motown. "I’m not really making fun of Dave Matthews. It’s hard to point to one line where I make fun of him. You just couldn’t do it."

On his third album, Downtown (Secretly Canadian), lifelong Bostonian Lennon sings no fewer than two catchy, irony-dripping songs about the Dave Matthews Band, the massively unit-moving groovester gurus to America’s academe automatons. In "Really Dave Matthews" (in which ex-Morphine man Dana Colley apes the baritone-sax squeals of DMB’s mountainous Leroi Moore), Lennon tells of a bored college kid who’s exposed to the South African’s ubiquitous dorm-room descants. ("She had Dave’s poster on her wall. When we were talking on her bed, she accidentally touched my hand. I was so happy that I lied and said I like Dave Matthews Band.") In "Matthews Comes Alive," Lennon tries to fill Dave’s shufflin’ shoes, relating the DMB’s early days playing "a college in Vermont, at the spring fling on the quad," as the man himself. ("This is a song about me, Dave Matthews, and the band I formed. It was, what, 10 years ago? At the Earth Day festival.")

Lennon’s dual Dave disses have gotten some chuckling attention from indie tastemakers. But the smirking hipsters who’ve taken to his wry, contagious songs with a knowing wink and nod may be surprised that Lennon swears he isn’t taking the piss. In fact the most he claims to know about the band is that their songs seemed to issue from every jukebox in every bar he drank in while recording Downtown. "I don’t really know much about them," he says flatly. "I don’t hate them. There are a lot worse bands. But they sure are very popular."

Very popular is something Don Lennon isn’t quite yet. Not even in his home town, though he’s put out three CDs (his first two, 1997’s Maniac and 1999’s Don Lennon, were self-released), is signed to a respected indie (Indiana’s Secretly Canadian is home to tragically hip artists like the Danielson Famile, Songs: Ohia, and Damian Jurado), and counts scene staples like Peter Linnane and Pete Weiss as frequent members of his band (Lennon also recorded all three albums at Zippah, the Brighton/Brookline studio Weiss and Linnane own.)

"I honestly don’t know much about it," he says when I ask what he thinks of his the Boston scene. "I never play here. It’s really hard to get a show. It’s easier for me to get shows elsewhere. I’m not gonna keep sending [bookers] my CDs and having them reject me."

Does he find it ironic that despite Downtown’s having received favorable reviews in high-profile rags like the Village Voice, and despite his having devoted pockets of fans in far-afield burgs like Minneapolis and Omaha, the best club dates he can get around here are sporadic stints at the Milky Way and a recent spot opening for Pansy Division at the Middle East (at Pansy Division’s request)?

"No, I’d say it’s totally typical of Boston. You see the same names [on club bills] over and over again."

Has he ever tried playing in something like the Rumble in a bid to boost his profile?

"No. I don’t even know what that is."

At first, it’s hard to believe this diffident, soft-spoken 28-year old, with a flop of hair almost concealing his eyes and a starched collar under his preppy sweater, is the same guy who tosses off polished, poppy, often laugh-out-loud-funny songs with titles like "My Favorite Rock Group" and "Hang Out with My Friends" with such breezy surety. Then I think back to the covers of Lennon’s first two albums: in both, he’s unsmiling and sporting a tie. For a moment I wonder whether his bemused interview persona is all an act. But with every cagy, soft-spoken answer he gives, it seems that much clearer that he’s more at ease expressing himself in songs than in sentences. Maybe that’s why on Downtown he sings one, "The Boston Music Scene," that says much more about his feelings:

When you meet them off stage, they can be really mean.

But I have still not lost all faith in the Boston music scene.

Although I should have long ago.

And in the Boston music scene I’m gonna open up the show.

That song’s ambivalence speaks to the personality traits that seem to be at work, and sometimes at odds, in Lennon’s music. He’s something of an outsider. Super smart. A little shy. Occasionally a wise-ass. Standing a little to the side, constantly observing, compulsively commenting. Sometimes he’s mordantly funny. Sometimes he’s tender. Sometimes his songs are elegiac. Sometimes they’re ebullient. Sometimes, it seems, he’s not sure what they are. A lot of the time, neither am I. Groping for a frame of reference, I ask the obligatory influences question.

"Mekons . . . Beat Happening . . . Galaxie 500, which led me back to Lou Reed and John Cale . . . Talking Heads . . . Jonathan Richman."

Richman is no surprise. Like his Massachusetts compatriot, Lennon specializes in grafting quirky apothegms about quotidian minutiae to quasi-simplistic three-chord structures. And his words and his music, like Richman’s, have much more resonance than was at first apparent — even if it’s still not clear exactly what they mean to say.

Lennon seems to have traced a different thematic path on each of his three records. And on each one his songs are about, well, normal stuff. Maniac (recorded not long after he’d graduated from Boston University), with songs like "Grad Student" and "Turn the Living Room into a Dance Floor," is about college and all that entails. He even beats Andrew W.K. to the spiked punch with a song cycle: "Party in September," "Party All the Time," and "Party Coordinator."

Yet instead of rocking hard, this trio swoon. And their titles are deceiving. These songs and his other vignettes about dance music and talking to girls are funny, but they’re also laced with pathos, a sense of vulnerability, even a vague foreboding. Take "Get Moving." The blithely tossed-off "I see my friends, and they’re movin’ in different directions" might refer to Lennon watching a sweaty dance-floor jumble. Or it could allude to watching college students get scattered by the vagaries of approaching adult life. Or maybe he’s just castigating college cliques. Or himself. It’s hard to say.

"The first album was about parties and friends, mainly because that’s what a lot of people did in college, and that’s all I heard people talking about. I thought I would try to sing about what people were really doing."

His sophomore effort, Don Lennon, is about, well, Don Lennon. "The second album ended up being about me. Ridiculously so, since no one had ever even heard of me." Nonetheless, it kicks off with a Kinky rave-up called "My Debut Album" that’s about Lennon bringing same to a party to use as background music and bragging conversation fodder. ("What did you do last summer?" "I recorded my debut album.") Other songs have titles like "DL ’97" and "Ich Heisse Don"; here he comments on substantive things like social mores and being disappointed in a band and feeling ill at ease in one’s own country. But his self-reflexiveness, his plaintively goofy singing, and the tunes’ upbeat melodies make one wonder whether he’s serious.

Pete Weiss summed up Lennon’s MO best when he wrote on his Web site (www.weissy.com) that the music is "double-reverse-ironic-with-a-twist." That’s what makes Downtown such a multifarious work. Although it does find Lennon and his band branching into genres like folk and French pop and pedal-steely country, its musical vocabulary — sweetly keening vocals, sprightly strummed jazz chords, bouncy ascending and descending keyboard riffs, melodic high-end bass trills, and propulsive, shuffling beats — is much the same as that of its predecessors. But Lennon’s lyrics gaze beyond himself, and beyond the BU campus, to look at a sweeping swath of high culture and low culture, nightlife and sex life, Bongwater and the Mekons. Downtown is saturated with pop culture, with lyrics that are clever and, as usual, funny. There’s just that nagging uncertainty about what they mean. "Lenny Kravitz and Lisbon" is an ostensible warning to the Portuguese capital that the dreadlocked dude on their arena’s Jumbotron will only love ’em and leave ’em. But if Lennon’s dissing Lenny, why doesn’t he say so outright? And why is the music so happy? In the pretty "John Cale," a swirling gust of jingle bells and viola, Lennon dreams of himself as his subject, speaking Welsh, being "fucked-up on heroin and speed and . . . saying all these nasty things about Lou Reed." Is it a piece of hero worship wrought as eloquent verse? Is he being a jerk? Or is he just having fun? In the bouncy sexcapade "Gay Fun," when Lennon winks, "Sometimes a word has two meanings — I think you know what I mean," what does he mean? Who is this guy?

Maybe it doesn’t matter. Lennon’s fans love his farcical, enigmatic lyrics and his crystalline pop sensibility for what they are. And if he’s not yet a big name in his home town, he may soon be able to look forward to a wider audience in the Gulf region. As one reviewer writes on that populist arena of rock-crit discourse, Amazon.com (where Lennon’s three-album average is a solid 4.8 stars out of 5), "Play this CD for the people of Iraq and they would agree that the USA is good."