Hourglass

His first studio album in six years, after New Moon Shine, reached number nine on the Billboard 200 and was his first top ten album in sixteen years. It won the Grammy for Best Pop Album in 1998, and Frank Filipetti won a Grammy for Best Engineered Album. Much of it was recorded on a Yamaha O2R mixer and three Tascam DA-88 recorders, early digital devices that top-level artists did not usually use then. It is dedicated to Don Grolnick, who died during the sessions in 1996.

The lyrics turn to his past and family. Jump Up Behind Me honors his father's rescue of him after the Flying Machine days, and Enough to Be on Your Way was inspired by the death of his brother Alex. Taylor told Rolling Stone the record was "spirituals for agnostics." Little More Time with You was a big adult contemporary hit. Yo-Yo Ma plays cello on two tracks, Stevie Wonder plays harmonica on Little More Time with You, and Sting sings backing vocals on Jump Up Behind Me.