Replay

In the mainstream-with-sci-fi-conventions category, Lisa Roberts recommended Ken Grimwood's Replay, originally published in 1986. It is (in some sense) the serious version of the movie Groundhog Day. A man repeats a chunk of his life again, and again, and again. There's no clear-cut purpose, though. He doesn't need to make one perfect day or one perfect life so much as experience it from different angles and be grateful for what he's got. He can make money by betting on horse races he already knows the winner of and investing in unknown companies that will make it big, but he can't stop Kennedy from being assassinated. He can marry his college sweetheart, but not reconnect with the woman who is also caught in a similar time loop. In the end, when he pops out the other end of his loop, he has to deal with life as it comes, one day at a time.

     (Two anachronisms which pop out painfully, and I note because I'm a nit-picking pain in the butt: The desk in the hero's office features Mies van der Rohe's Barcelona Chair, which is a lounge chair, not a desk chair. Our hero is drinking Glenlivet scotch in a New York bar in 1964 --- to the best of my knowledge, the only bottle available in the US at that time had been smuggled into my father’s liquor cabinet from Scotland as a gift by an Inverness-bred friend of his: it wasn't generally available until the late '70s.)