Fail Again: The Family Business with Robert Downey Jr.

This episode originally aired July 22, 2025

The spotlight has certainly taken its toll on Robert Downey Jr. over the years. But much like his beloved MCU character Tony Stark, there's an undeniably powerful force inside Robert that keeps him pushing forward. When we sat down over iced coffees, we found ourselves unpacking the fraught relationship Robert had with his father — the experimental, countercultural filmmaker Robert Downey Sr. — whose unconventional lifestyle created lasting ripples throughout the family. Their shared documentary, “Sr.”, stands as a powerful testament to the healing they found. Plus, we talk about sobriety, the belief it took to become Iron Man, and the full-circle moments spanning the decades since we first crossed paths on the set of Chaplin.

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