Cutthroat Island Rocketeer Last Action Hero Shawshank Redemption Cast Away - Not too sure how this one did at the box office, but I love Tom Hanks and the interaction with "Wilson"
The Black Hole Clash of the Titans Tron Last Starfighter Real Genius Prince of Darkness They Live The Thing (1982) Cobra Last Boy Scout Innerspace The Burbs The Three Amigos Adventures of Ford Fairlane Body Double Dragnet The Evil Dead Trilogy
A lot of the movies being listed so far seem like they were successful in a critical sense even if they didn't make money in their initial release. A couple of movies I like to watch that have never been regarded as successful in either sense are Sky Captain and Small Soldiers
Not sure about the box office success/failure of these two but here goes. Drowning Mona. Excellent cast, lots of little stuff going on you won't notice unless you really pay attention, and just plain silly. Also, Jumanji. Robin Williams, Bonnie Hunt, rather unique story line, lots of action (after a somewhat slow start) and just plain fun.