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Probably a combination of directors/studio execs not being able to neatly fit him into a box, plus him purposefully pursuing things that interested him over whether they would be box office hits or not. I think a lot of actors choose "badly", but they have a career that they're proud of and enjoy despite audiences not being able to share that. I'm just sad he never got to feature in a Sister Act movie so we could get a Goldberg/Swayze reunion - imagine him as a rival choir leader? Missed opportunity if ever I saw one.
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