01/16/2013 11:37 am ET Updated Mar 18, 2013

From '80s Teen Icon To Jazz Chanteuse: Molly Ringwald Hits New York's 54 Below

It's official: Samantha Baker, Andie Walsh and Claire Standish have all collectively grown up.

Well, the woman who played all three of them has done so, at least. Molly Ringwald, whose starring turns in Pretty in Pink, Sixteen Candles and The Breakfast Club made her an '80s teen icon, morphed almost seamlessly into a silk-voiced jazz chanteuse on the stage of New York's 54 Below nightclub Jan. 15.

As it turns out, Ringwald's latest role was actually more of a return to her roots than a reinvention: as the 44-year-old star told the crowd, she got her start singing alongside her father, blind jazz pianist Bob Ringwald. Describing jazz music as her "comfort food," Ringwald dove into a set featuring standards made famous by Billie Holliday, Blossom Dearie and Bing Crosby with brass and panache. (Many of these tunes have been brought together for a forthcoming album, Except... Sometimes, due out April 9)

Molly Ringwald At NYC's 54 Below

"I don't feel any pressure with music; it's something that I do because I love it," Ringwald told me at a press event shortly before the show. "I believe in evolution; I don't believe in re-invention. I think most people are really excited when they find I can sing. It's like a party trick."

To be fair, the end result is a bit of a mixed bag. It's easy to see how Ringwald charmed New York audiences during her stints both on Broadway (Cabaret) and off-Broadway (Jonathan Larson's tick, tick... BOOM!). Describing herself as having a "bohemian soul," the star is clearly in her element with showtunes, and her vocals soared in jazzy arrangements of "On the Street Where You Live" from My Fair Lady and "Where Is Love" from Oliver. She felt compelled to apologize for her rudimentary pronunciation on the popular French song "J'Attendrai," but at it turns out, her warm stage presence and playfully unscripted, if limited, stage banter (a mid-song request for a prop martini was quickly accommodated by the wait staff) made up for any phonetic discrepancy, as the number was easily one of the evening's highlights.

It's a shame, then, that a handful of other tunes felt forced at times. Her take on the Stephen Sondheim-penned "Sooner or Later" from 1990's Dick Tracy was curiously tentative, lacking the slinky sizzle of Madonna's original. A rendition of Billie Holliday's "Don't Explain" was adequate but nonetheless forgettable, while her efforts to turn an intimate version of the Simple Minds anthem "Don't You (Forget About Me)" -- an otherwise well-sung nod to her John Hughes movie legacy -- into a rapturous audience sing-along fell flat.

Still, Ringwald infused "I'll Be Seeing You," the 1938 standard that was repurposed in the late 1980s as an AIDS crisis anthem, and "I Get Along Without You" with the same effortless charm she displayed so memorably on the big screen (and continues to do as a cast member on The Secret Life of the American Teenager). She may never rival Holliday, Lena Horne or even Diana Krall musically, but overall, she left her 54 Below audience in a sunny, spirited mood that belied the chilly temperatures outside. With a bit more fine-tuning, the role of a smoldering nightclub ingénue could be Ringwald's for the taking.

Molly Ringwald plays New York's 54 Below again on Jan. 16. For more details, click here.