Donning designer eyewear reminiscent of ʻ90s indie diva Lisa Loeb, Ingrid Michaelson was greeted warmly last Thursday at City Winery by a devoted hometown following. Not a table was empty nor refined palate left dry at the New York City jazz club-meets-wine bar, as eager fans had been waiting for the first Staten Island nativeʼs return home to the Big Apple since December.

Admitting to being the “most nervousnessst” she had ever been, Michaelsonʼs quick wit and dry humor carried on throughout her performance as she proved that she wasnʼt afraid to let loose a bit. “Itʼs pretty classy in here, huh?” she said, “Iʼm used to playing in clubs with penises drawn on the walls.”

As she rifled through much of her debut Girls and Boys and the follow-up, Be OK, a collection of new material, live recordings and covers, Michaelson rotated between electric piano and ukulele. Backed by Allie Moss and Bess Rogers on guitars and Elliot Jackson and Chris Kuffner on drums and bass, she joked about singing off-key and poked fun at Miley Cyrusʼs inability to keep proper time. “Breakable” was a tale of stereotypical, fragile-little-girl-syndrome, while “Overboard,” a livelier poppy girlish anthem about overcoming brokenness, livened the near depressive setting. “Iʼm a big girl now, in my big girl shoes,” she yodeled like Regina Spektor as I wondered where all the 16-year-olds were (oh yeah, I was at a bar).

While Michaelson may not hold a masterʼs in music theory, her songs were wholesome, thoughtful and refreshing. “I am giving up on half-empty glasses/I am giving up on greener grasses,” she sang in “Giving Up,” a track about just the opposite and a solid message to adolescent angst. Michaelson also showcased a cover from her previous nightʼs performance at the R.E.M. tribute show at Carnegie Hall, followed by a Weird Al-type rendition of “Ob-La-Di, Ob-La-Da,” the lyrics rearranged to express her esteemed obsession with the popular television series, Lost: “Ob-La-Di, Ob-La-Da… I love Lost!”

An obvious fan favorite and personally deemed “little fart of a song,” “The Way I Am” was another example of Michaelsonʼs loving nature, with hokey verses like, “Iʼll buy you Rogaine when you start losing your hair.”

Although the modest Michaelson has yet to sign with an official record label, her near overnight success thanks to song placement in Greyʼs Anatomy (the melodic “Keep Breathing” was written at producersʼ request) and an Old Navy commercial, is another example of the do-it-yourself artistry that is slowly reshaping the industry she finds herself a part of.