In 2005, Robert Downey Jr described Kiss Kiss Bang Bang as the first film in "like 70 tries" that "works from beginning to end" and felt "innovative and fun to do." The remark came at a pivotal moment: his career had been left in tatters by years of drug addiction, arrests and rehab, including being sacked from Ally McBeal after a relapse, which made him effectively unemployable and uninsurable in Hollywood. The comedy caper is often viewed simply as the start of his comeback, but at the time it represented proof to Downey Jr himself that his career could still work.

The film, directed by Shane Black, cast Downey Jr as thief Harry Lockhart, who poses as an actor in Hollywood and becomes entangled in a murder investigation alongside private detective Perry van Shrike, played by Val Kilmer. It arrived around the same time his future wife, producer Susan Levin, gave him an ultimatum to stay clean or lose her, a challenge he met before the pair married in August 2005. Downey Jr, previously an Oscar nominee for Chaplin, later reflected that he refused to give up on his career or sobriety, saying "I was done when I was 30… it just took me another ten." The film's success helped pave the way for his later casting in Iron Man, which cemented one of Hollywood's biggest comeback stories.