1. Lauryn Hill "Lost Ones" (1998)
Album: The Miseducation of Lauryn Hill
When she decided to create her solo debut, The Miseducation of Lauryn Hill, Lauryn Hill took to Tuff Gong Studios in Jamaica to record a 14-track multi-Grammy-winning classic album. From the interpolation of Sister Nancy's "Bam Bam" to the spicy patois in her raps, "Lost Ones" perfectly defined the Jamaican influence on Lauryn's work.
This song was her first shot at a solo career; it was more than that though, "Lost Ones" was the sound of a brilliant artist breaking away from the boys and demanding respect on her own, which was obviously well-deserved. L Boogie's recording engineer, Gordon Williams, once detailed the recording of this legendary track. On the first morning they arrived in Jamaica, Lauryn gathered around 15 of Bob Marley's grandchildren at the Bob Marley Museum on 56 Hope Road and began singing "Lost Ones." That experience inspired the lyric, "I was hopeless now I'm on Hope Road. Lauryn laid the verses on a handheld microphone for this track, and you can feel the energy in the final recording.
She went in on first line, "It's funny how money change a situation," and by the time she got to the chorus—"You might win some but you just lost one"—it was obvious that the song was a shot at former Fugees Wyclef Jean and Pras. The song became a highlight of Hill's classic album because it showed off all her strengths—sweet singing, razor-sharp mic skills, heavy-hitting production, plus versatility and fierce determination to stand on her own two feet. That's why this jam belongs at the top of the list. —Lauren Nostro