On the surface, at least, the pairing of headliner Lloyd Cole and opening act Jill Sobule downstairs at the Middle East a week ago Wednesday was an odd one. He’s a dour, dark-maned Scottish expat who’s been brooding about New York City for the past decade, having made his mark as an underground pop favorite in the ’80s. She’s a bubbly blonde Denver native who emerged in the alterna-’90s with the novelty hit “I Kissed a Girl.” But NYC can make for some strange bedfellows, and Sobule and Cole are a pair of cult singer-songwriters who’ve found some common ground: she now plays guitar full time in Cole’s touring band — the Negatives — and is a featured member of the group that backs him on his latest CD, The Negatives (March). Cole was happy — well, he didn’t look any more bummed out than he usually does — to return the favor at the Middle East, where a modest yet respectable-for-a-Wednesday-night crowd of a couple hundred had gathered for the double bill. Toward the end of Sobule’s solo set, a scruffy Cole emerged to enthusiastic cheers and accompanied her on guitar for a couple of tunes, including “I Kissed a Girl.”

Cole may not be as playful as Sobule, but he does have a wry sense of humor. So he opened his set with an attempt to bring the audience down to his level by announcing, point blank, that “the Red Sox will start to lose soon.” Sensing he’d struck a raw nerve, he tried to be a good sport about it: “You know what? The rest of the world wants the Red Sox to win so you can just shut up about it.”

With that, he launched into the opening cut of The Negatives, “Past Imperfect,” a surging, sentimental mid-tempo pop tune gently propelled by a four-piece backing band that featured Sobule and bassist Dave Derby (formerly of the Boston-based Dambuilders) rocking out to his right. Cole, for his part, didn’t rock so much as roll with the punches, and that’s always been his MO. On stage (and probably off), he plays the role of the stoic romantic given to fits of melancholy reflection. It almost seemed out of character when he joined in with the band as they broke into the intro to Springsteen’s “Born To Run” right before playing “Man on the Verge,” a new tune that finds Cole wrestling with midlife crisis. And, no surprise, it was Sobule who took over the lead vocals for a cover of the Destiny’s Child tune “Survivor” during the encore — which, by the way, was dedicated to David Cone, the hard-luck Red Sox pitcher who, perhaps inspired, would start and win the following night.