Roy Wood Jr. On Bombing at The Apollo & How Failure Fueled His Success

Comedian and Author Roy Wood Jr. sits down with Craig Melvin on this week’s episode of Glass Half Full for one of his most personal conversations yet. Roy opens up about his complicated relationship with his father, bombing early in his career at the Apollo Theater, and the reason he left The Daily Show. Roy also shares how becoming a father forced him to confront his childhood and choose a different future for his son. This episode of Glass Half Full originally aired on May 5th, 2026.