After the critical (and commercial) success of her debut two years earlier, Rickie Lee Jones had a lot riding on her sophomore album, Pirates. From the opening track, "We Belong Together," Jones served notice that she was willing to challenge herself and experiment with more unusual, complex song structures. Her unique phrasing and style reflect her interest in beat poets and the bohemian lifestyle, and on this album she relies on more obscure imagery than the direct, detailed observations on comrades used on her first album. There are a wide range of musical influences represented (rock, jazz, soul), but the acoustic arrangements are more piano-based than most of her other albums. While there is an undercurrent of reflection on failed romances, Jones also reveals her playful side with songs like "Woody and Dutch." The musical and lyrical variety on the album is best represented in the album's centerpiece, "Pirates (So Long Lonely Avenue)," where she moves through mood and tempo changes with ease. Although the songs may not immediately grab the listener, the lyrical and musical complexities ultimately make this album more rewarding with every listen.