Kiss Kiss Bang Bang

Kiss Kiss Bang Bang is the film that saved Robert Downey Jr.'s career. Shane Black's directorial debut is a meta-noir comedy set in Hollywood, where a petty thief accidentally auditions for a movie, gets paired with a gay private detective named Gay Perry, and stumbles into a real murder mystery. The film breaks the fourth wall, mocks its own genre conventions, and features the sharpest dialogue of the 2000s.

Val Kilmer's Gay Perry is one of the great underrated comedy performances — a tough, competent detective who happens to be gay and is perpetually exasperated by Downey's incompetence. Their chemistry crackles. Downey's narration — where he constantly forgets details, backtracks, and argues with himself — is a masterclass in unreliable storytelling that predates Deadpool by a decade.

The film flopped in 2005 because Warner Bros. released it in only 600 theaters with minimal marketing. But it proved to Jon Favreau that Downey could carry a blockbuster, directly leading to his casting as Tony Stark in Iron Man. Without Kiss Kiss Bang Bang, there is no Marvel Cinematic Universe. The most consequential box-office failure in Hollywood history also happens to be one of the funniest films of its decade.