Why did it fail?

This film seems to have fallen through the cracks. It hardly gets shown on TV. It was not a commercial success when released. Why?

I think that it was trying to be both a buddy movie, and also a satire on the Secret CIA War in Laos. There is not enough satire, and the two main leads are presented as nice guys. Mel Gibson was still a huge star and Robert Downey Jr was a rising star, but the film does not portray them as morally corrupt pilots, but more as lovable rogues. In reality, anyone working for Air America would be keenly aware of who they were working for and what they were really doing. The airline was a CIA front that was involved in the drug trade in South East Asia. This was American policy and not the idea of some rogue CIA agents as the film implies. This is a film that pulls its punches.

Compare this film to The Three Kings , which has is critical of American foreign policy, is a satire on the media AND is a heist movie.

Maybe Air America can be re visited as a Netflix series, as there was/is a story to be told about what was going on in Laos in the late 1960s.