Falling Down (1993), Freeway (1996) are two that I saw fairly recently and the 90’s were jumping off the screen.
Pauly Shore had 90’s career. Encino Man (1992), Jury Duty (1995), Bio-Dome (1996). His only movie of the 2000’s was Pauly Shore is Dead (2003) which was about no one caring about him anymore.
Prior to Trump it was mostly fringe candidates like Storm Thurmund (1948), George Wallace (1968), David Duke (1988, 1992), Pat Buchanan (1992, 1996).
In terms of major candidates, there are some questionable endorsements for candidates like Nixon and Reagan. But you have to go all the way back to Woodrow Wilson to find a president who was openly happy about receiving those endorsements.