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

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

August 18, 2026 · 41 min · Episode 25

About this episode

Roy Wood Jr. discusses his early career failures, his relationship with his father, and the impact of fatherhood on his life.

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.

People in this episode

Host: Craig Melvin

Guest: Roy Wood Jr.

Mentioned in this episode

Organizations: The Daily Show

Places: Apollo Theater

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