I was just reminded of the existence of Who’s Your Caddy? from 2007, a film that’s noteworthy for having Jeffrey Jones in a major role just 5 years after he plead “No Contest” to child pornography charges, and it was executed produced by Harvey Weinstein who’s obviously been convicted of Rape since then.
So a movie with two convicted sexual predators in it, do we have anything that can beat that? Also not looking at drug charges, it has to be for really scummy stuff.
Does “Gimme Shelter” count?
I had never heard of this film. However, IMDB credits Lil’ Wayne with an acting role in it, who by himself probably puts the movie into contention for most convictions by the cast. And per your prohibition on drug charges, many of his convictions were firearms related!
Tom Sizemore (assault & battery) and Danny Trejo (armed robbery) in Five Thirteen.
My understanding is that Trejo was in and out of juvenile facilities, and then prisons, from the mid '50s through (probably) 1969, for a variety of offenses, such as drug dealing and assault (including hitting a prison guard in the head with a rock during a riot), as well as, apparently, a lot of drug use.
The watergate documentary has interviews with all the convicted Watergate burglars:
The Great Jesse James Raid paired Tom Neal and Barbara Payton. Neal served hard time for beating Payton’s husband Franchot Tone within an inch of his life. She was in and out of jail when she transitioned from B movies to B girl.
I didn’t mention either actor’s drug offenses, per the OP. Domestic assault and battery and armed robbery elevate beyond, for example, Robert Mitchum’s arrest for marijuana possession.
From IMDB:
Leo Gordon had served five years for armed robbery at San Quentin State Prison.
Producer Walter Wanger served a four-month prison term for shooting agent Jennings Lang, whom he suspected of having an affair with his wife Joan Bennett.
Actual inmates who were incarcerated and guards at Folsom State Prison at the time this movie was made are featured as extras.