Amy Winehouse - Frank (2003/2015) [Official Digital Download]

If a series of unfortunate comparisons (like the ones to follow) cause listeners to equate British vocalist Amy Winehouse with Macy Gray, it's only natural. Both come on like a hybrid of Billie Holiday and Lauryn Hill who's had a tipple and then attempted one more late-night set at a supper club than they should have. Despite her boozy persona and loose-limbed delivery, though, Winehouse is an excellent vocalist possessing both power and subtlety, the latter an increasingly rare commodity among contemporary female vocalists (whether jazz or R&B). What lifts her above Macy Gray is the fact that her music and her career haven't been marketed within an inch of their life. Instead of Gray's stale studio accompaniments, Winehouse has talented musicians playing loose charts behind her with room for a few solos. Instead of a series of vocal mellifluities programmed to digital perfection, Winehouse's record has the feeling of being allowed to grow on its own – without being meddled with and fussed over (and losing its soul in the process). Simply hearing Winehouse vamp for a few minutes over some Brazilian guitar lines on "You Sent Me Flying" is a rare and immense pleasure. Also, like Nellie McKay (but unlike nearly all of her contemporaries), Winehouse songs like "Fuck Me Pumps," "Take the Box," and "I Heard Love Is Blind" cast a cool, critical gaze over the music scene, over the dating scene, and even over the singer herself. With "In My Bed," she even proves she can do a commercial R&B production, and a club version of "Moody's Mood for Love" not only solidifies her jazz credentials but proves she can survive in the age of Massive Attack.