Time Stamp: 1999 - 2003

Claudette Ortiz. Ryan Toby. Robby Pardlo. Claudette dated Robby in high school. The two formed a group. Then they brought in Ryan. The three became City High. Wyclef signed them. Got nominated for a Grammy. She broke up with Robby while they were still a group to start dating Ryan (awkward!), and later married Ryan and had a baby with him. Last year, Robby appeared on A&E's Intervention revealing his battle with alcoholism, citing the Claudette and Ryan situation as a tipping point. “What Would You Do?”