Lauryn Hill is ready to record again! But hey, what about her Sister Act 2 co-star and fellow former Wyclef Jean associate Ryan Toby, who, along with (future Intervention-subject) Robby Pardlo and (Pardlo’s girlfriend and future ex-Mrs. Toby) Claudette Ortiz, recording as City High, scored a terrific surprise hit in 2001 with the song “What Would You Do?”.
The song, a conversation between a guy at a party and a woman he knew from when they were kids who’s now working as a stripper and turning tricks on the side, treads a tricky line between passing judgment and urging empathy. It was an unusually earnest, message-y song more fitting the social consciousness of the late 80s than the blingy-clubby early Aughts (Toby actually scored his biggest hit as a songwriter with Will Smith’s “Miami”), but somehow it overcame, and damned if it doesn’t still sound great and feel resonant.
Still, City High had trouble following it up – a second single “Caramel” did just all right. Meanwhile, tense group dynamics (putting it lightly) led to their break-up, and their self-titled album was their last. Toby did release a solo album called The Soul of the Songwriter in 2006 which came and went without much notice, but hasn’t put anything out since. Where is he now? YouTube, of course.
City High “What Would You Do?”
