Josie and the Pussycats.

It was so far ahead of its time that critics just didn't get it because the world they were satirizing was still about a decade away. (Instagram, fame, product placement, fanboyism...)

Also, bonus answer. The Big Hit. Because fuck it. Lou Diamond Phillips knew exactly what kind of shclock movie he was in and chewed the scenery fantastically.

Bill and Ted's Bogus Journey

STATION!

Jingle All the Way (the original, not the abomination with Larry the cable guy). 19% RT.

I think most people think it's too "weird", but I genuinely love it. It's got all the great 90s tropes, a cartoony core in a live action movie, an anti-consumerism message in a Christmas movie, and Phil Hartman. What's not to love?

I am pretty sure every movie I really like is under 60% on RT.

Maximum Overdrive (1986): 14%

It's dumb as shit, and I will always love it for that reason.

Civil War. I don't know the rating on Rotten Tomatoes, but I do know that it is a recent movie, and 196 sent me here lol

I really enjoyed the concept and story of In Time, which apparently has a 37% tomato meter and 51% audience score. That was probably the first less than 60% one I saw I particularly liked.

Edit: I take it back, I choose Elysium. It has a 59% audience meter and I frickin LOVE that movie, all the way down to the villain being super crazy and virtually unintelligible.

Maximum Overdrive

Passengers is a pretty cool sci-fi movie. I like the first half in particular, the way it shows how "dumb" A.I. will be the bane of our existence feels very accurate as far as futuristic predictions go. I'm also a sucker for "lost on an island" stories, which this ultimately is. I will never understand how so much was made about the decision the main male character makes at a certain point, because the movie very clearly shows that a) he really struggles with the decision for a long time, knowing it's wrong and b) finally does it after almost killing himself and being heavily intoxicated, immediately regretting it. The only real gripe I have with the movie is that Chris Pratt and Jennifer Lawrence have zero chemistry, which kind of kills the whole romantic element of the film.