Robert Downey Jr was nominated for Best Actor for Chaplin at twenty-seven and then spent a decade in and out of prison and rehabilitation, effectively uninsurable and unemployable in studio film.
Iron Man was made against studio resistance to his casting, and his improvisation on it set the conversational tone the entire Marvel series adopted. The final line of that film was not scripted.
Zodiac, Kiss Kiss Bang Bang and Tropic Thunder show the range in the same period, the last earning a nomination for a performance that should have been career-ending and was not.
He won Best Supporting Actor for Oppenheimer, playing a small resentful man, which is the furthest thing from the persona he built.