Mona Lisa Smile's best moments come from performers who don't try to emulate icons from the past or treat the songs like jokes: Chris Isaak's "Besame Mucho" is just as swoony as the versions that made it a standard during the '50s, but doesn't imitate any particular rendition similarly, Kelly Rowland's "I'm Beginning to See the Light" is playfully flirty enough to sound like it could've been a hit in that era without trying too hard to emulate the styles of the time. Likewise, the Trevor Horn Orchestra's "Istanbul (Not Constantinople)" and "Sh Boom," as well as Elton John's "The Heart of Every Girl" (the album's only original song) are a little too cutesy for their own good.
Yet these songs are better than Tori Amos' overly theatrical readings of "You Belong to Me" and "Murder He Says," which go beyond amusingly quirky to annoyingly quirky. Seal's "Mona Lisa" and Macy Gray's "Santa Baby" come so close to sounding like the versions popularized by Nat King Cole and Eartha Kitt, respectively, that it almost seems pointless to have recorded the new renditions in the first place. The soundtrack takes the utmost care to sound like an artifact from the early '50s, which is refreshing and frustrating in equal measure. The soundtrack to Mike Newell's Mona Lisa Smile, a Dead Poets' Society-like film set at a women's college in the '50s, features a wide array of contemporary artists covering standards from that decade.