95. Jill Sobule, Pink Pearl (Beyond, 2000)

“This is my best album” says Sobule, and although it’s not the one with the immortal “I Kissed A Girl” (on 1995’s self-titled effort, easily her second-best), its indie label should tell you why she holds it in such high regard. After a career of seeing her major label efforts mostly flop, get ignored, or not get released at all, this one breathes with freedom and self-confidence. The protagonists, from “Claire” (an ordinary elderly woman sifting through memories of an extraordinary life) to the optimistic, medicated soul of “Rainy Day Parade”, are all rendered with Sobule’s witty, watchful, caring eye. Admirably, she makes you laugh and breaks your heart song after song, culminating in the closer, “Rock Me To Sleep”, a quietly devastating lullaby like few others.