Was it Free Money? Sounds just like you're describing with the idiots who love the warden's daughters.
Walrus-like warden, Sven "Swede" Sorenson, a cross between Bluto and
Wimpy, runs the prison, murders convicts who escape, and has the FBI
on his trail in the form of agent Karen Polarski, the daughter of the
town's corrupt judge. Swede's twins tell their father they're pregnant
(they aren't), so he pushes their dim boyfriends, Bud and Larry, into
shotgun marriages. He also turns his sons-in-law into slave labor, so
Bud hatches an escape plan: to rob a train carrying old bills to the
mint for burning. Larry's his reluctant accomplice. When Bud is
captured and railroaded into Swede's jail, his death looks certain,
until he hatches yet another plan that requires Larry's help.
Source: Free Money - imdb
Looked for quite a while and this was the only one I could find that seemed to fit. Released in 1998.
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