Elliott Smith is the very model of a modern oho troubadour. He writes intimate cafe ballads that suit his breathy voice, filling his songs with emotional wreckage; the man knows how to give bad love a good name. Smith started out as just another muffled folkie choking on his own self-pity, but he lightened up with a bang on 1997's excellent Either/Or. He also cut a dashing figure at the Oscars, singing his Good Will Hunting theme song, "Miss Misery," and wound up taking a bow while holding hands with Celine Dion and Trisha Yearwood. (Smith wore a suit to the ceremony but evidently forgot to wash his hair – now that's credibility for you.)

XO, his fourth solo album and his major-label debut, features his most adventurous music ever, opening up his acoustic flow with piano, horns, vocal overdubs, even a string section. Smith still has a love jones, and he's still a heartache looking for a place to happen. But he has an easier touch with his beautiful-loser stories. "Baby Britain" is one of the saddest drinking songs you've heard since Leonard Cohen discovered yoga, but it bounces along with a cheery Sesame Street piano riff. "Independence Day" swings like Paul Simon in the Seventies, while "Oh Well, Okay" creates a gorgeous Brian Wilson homage out of Pet Sounds keyboards. The languid misery of songs like "Tomorrow, Tomorrow" and "Bled White" is pretty much perfect if falling hopelessly in love with all the wrong people is your idea of a good time. From the sound of XO, it's Elliott Smith's idea of a great time.

“1999”

“I don’t consider myself a great poet,” Prince told Rolling Stone. “I just know I’m here to say what’s on my mind.” In the case of the apocalyptic party anthem “1999,” he was worried about then-president Ronald Reagan’s foreign policies. The song’s melody is based on a riff borrowed from the Mamas and Papas’ “Monday, Monday,” and Prince originally envisioned the first verse with three-part harmony but later split the vocals between himself and members of the Revolution. Because Warner Bros., with whom Prince was locked in a contractual battle, owned the original’s masters, Prince rerecorded the song and appropriately released that version in 1999.