Robert Downey Jr 1999
Vintage Cap

On August 5 1999, Superior Court Judge Lawrence Mira revoked Robert Downey Jr.’s probation after the actor admitted missing a string of court-ordered drug tests that traced back to a 1996 cocaine-and-heroin arrest.

The judge handed Downey a three-year prison term, and later that month the 34-year-old was processed at the California Substance Abuse Treatment Facility & State Prison in Corcoran. There, inmate P50522 donned a red jumpsuit and posed—smiling faintly—for the booking photo you see here, the placard reading “CSATF /SP P50522 DOWNEY.”

Downey ultimately served about a year before winning early release in August 2000, but the image became an enduring symbol of both the depth of his addiction and the starting point of one of Hollywood’s greatest comebacks.

Less than eight years after this picture was taken, he would land Iron Man, launch the Marvel Cinematic Universe, and transform the faded mugshot into a badge of resilience instead of disgrace.