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Michael McDonald was the Akon of the '80s. Ubiquitous, inescapable. The consummate guest star, backing vocalist, and duet partner, trading lines with everyone from James Ingram to Patti LaBelle to Kenny Loggins to his own sister. Like top-shelf vodka, his bubbly, mush-mouthed yodel (wherein murdered consonants ascend to heaven and are awarded 72 virgin vowels) enhanced and intoxicated whatever you mixed it with. Consider Steely Dan's "Peg," his note-perfect bleats finely chopped like pristine lines of cocaine, a sublimely OCD mingling of the perfectionist and the populist, the alien and the instantly familiar. Only one fate can befall a voice so memorable, so distinct: Nowadays, he's a bit of a joke.

A joke Mike's in on, though, at least to an extent. In 2008, he has evolved into a slightly less athletic Chuck Norris. A kitschy pop-culture punchline masterfully wielded by The 40-Year-Old Virgin ("Ya mo burn this place to the ground"), The Family Guy ("Faaaaart!"), the brilliant Internet serial Yacht Rock ("California vagina sailors"), and even power-pop stars the New Pornographers, who held a YouTube contest in which fans submitted videos of themselves singing NP tunes in the inimitable Michael McDonald style. (Some guy with an atrocious beard won for warbling "It's Only Divine Right.") The Family Guy joke is most instructive: Mike is hired to sing backup vocals to everything anyone says, because it all just sounds better—sweeter, smoother, more soulful—when issued from his lips. Not a bad rep. It wouldn't be quite so bothersome, though, if these days he didn't mostly sing old Motown songs.

We're live last Wednesday night at the Blue Note for the sold-out Michael McDonald show. That is not a typo. Aside from the sax guy briefly evoking A Love Supreme during the intro vamp to "I Keep Forgettin' " (that'll probably cost you a few virgins, pal), this is no hackneyed jazz crossover plea—before a euphoric crowd, Mike instead grinds through 90 minutes unifying the two halves of his estimable career: the cheerily smooth r&b on which he built his fortune ("What a Fool Believes" triggers mass hysteria), and the cheerily smooth renditions of classic, often not traditionally smooth r&b songs that've dominated his last several albums (a superfluous take on "I Heard It Through the Grapevine" triggers significantly less hysteria). His new Soul Speak, third in a trilogy that includes the instructively titled Motown and Motown Two, tosses in a couple of flaccid originals and a few bewildering tributes from farther afield: Mike's take on "Hallelujah" can't match the profundity of that American Idol dude's version, let alone Jeff Buckley's. His backing band tonight hails from the to-save-the-song-we-must-destroy-it Vietnam school, unnecessarily bombastic solos and all. For protection and companionship, I have brought along three martini-swilling associates, and we struggle mightily as to the degree of irony with which we are enjoying ourselves, or not. Nearby Blue Note patrons are visibly alarmed by our (relative) youth; that not every last person in the joint is bone-white befuddles us in turn.

It's complicated.

Anyway, "Oh, you're gonna pay, guitar!" howls one of my martini-swilling associates as the lead guitarist's face contorts violently while searching for that perfect, sweet, climactic note. For convenience's sake, we assign every side player to a bygone TV star: Beau Bridges on guitar, Wilford Brimley on sax, etc. Mike's drummer is evidently nicknamed "Baby Girl." As for the man himself, he remains middle management incarnate, his hair and Brillo-pad goatee a resplendent shock of white; the spit starts flying by the middle of the towering opener "(Your Love Keeps Lifting Me) Higher and Higher," and the sweat is pouring freely just a few songs later, coating his cheeks to almost strategically suggest that Mike is crying. He pounds his electric keyboard and yodels his ass off. "I know what's good for you, baby," he violently coos, and you get to thinking that maybe he does.

You watch a guy like this close his set with a triumphant double-shot of Stevie Wonder songs, and you can't help but think it: Pat Boone. But does the elated throng here actually prefer Mike's version of, say, "Walk On By" to the original? Doubt it. Hope not. He avoids any outright debacles, though, and his mercifully solo reading of "You Don't Know Me"—the Ray Charles version—is the killer tonight, a Lifetime movie tearjerker that earns its pathos, even if it's borrowed. My martini-swilling associates are right to point out the grueling irony of covering "Ain't Nothin' Like the Real Thing," but ah, screw it. The oldies album is the official baby-boomer exit strategy. It's not his fault. And it's heartening that "Takin' It to the Streets," from Mike's original meal ticket, the mighty Doobie Brothers, inspires the most crowd rapture tonight, folks leaping to their feet and clapping awkwardly but endearingly as our hero's sweat pours forth. He's got his own canon, thank you very much.

But Michael McDonald remains a truly confusing notion in 2008, an ironic mustache of a man, alternately appalling and appealing, but bewildering throughout. Before he rips into "What's Goin' On," Mike deigns to make a political statement that I, in my vertiginous state, completely misread. He announces that we stand at the threshold of what could be a great time, and praises "the one guy" who could lead us to that promised land. The gender specificity of this statement is immediately obvious, but what follows somehow is not. "I love when politicians talk about how they can't wait to get into office and cut all that wasteful spending," Mike chortles. "We know what that means, right? It means they take all the money from us hard-working people, and they line the pockets of their friends." Huge audience whoops, including from the nice lady next to me who, as the lights had gone down, had been telling her neighbor about how "Giuliani is a great man."

I thereby read Mike's monologue as a direct endorsement of a) McCain, and b) Bush's tax cuts. My martini-swilling associates, however, insist he was backing Obama. In the cold light of reason, their take seems much more feasible; the man himself remains as unfeasible as ever. We stagger out into the East Village night, quotation marks spinning around our heads; we may be fools, but we believe nonetheless.