Replay

A 1986 Novel by Ken Grimwood.

Jeff Winston is 43 and stuck in a loveless marriage and dead end job. At 1:06pm on October 18, 1988, he has a sudden, fatal heart attack and the next moment finds himself 18 in his college dorm room in May of 1963. He makes a killer bet on who he already knows will win the Kentucky Derby and uses his winnings and knowledge of the future to create a Fortune 500 company. By 1988 he is wealthy and powerful... and on October 18, 1988 he suffers another fatal heart attack, waking up in 1963 again.

Yep, he's stuck in a 25 year Groundhog Day Loop. Each time he loops back though, he's a little further along his original timeline - and what's going to happen when the loop back point and the day in 1988 eventually meet?

He meets Pamela, a woman who is also stuck in the loop. Together they find some stability in their lives and seek out others who may be looping themselves.

Tropes Present in this work:
""I did it for you. For us. No one else can understand it; you'd be amused at the interpretations some of the critics have come up with.""
 * Alternate History: Given the length of time this character loops, each "replay" is one of these by differing degrees.
 * Author Existence Failure: Ken Grimwood was writing a sequel when he died in 2003.
 * Cloudcuckoolander: One of a darker variety.
 * Dead Little Sister:
 * Driven to Suicide: Jeff's college roommate, Martin, committed suicide in the original timeline.
 * Do Well but Not Perfect: Jeff becomes a billionaire his first replay, but on subsequent runs tries to simply make enough to be comfortable and not draw attention to himself.
 * Foreshadowing:
 * Free Love Future: Jeff's girlfriend in 1963 wants to help him get off but remain a Technical Virgin. She is horribly offended when he suggests having sex and asks to be driven home. Jeff muses to himself that things are a little more loose in the "future" time of the 1980's.
 * Yet during a different replay when he has a lot of sex and experiments with drugs he muses to himself that the future of the 1980's has AIDS.
 * Everyone Is Jesus in Purgatory: Invoked in-universe in an art exhibit Pamela made for public viewing but knew only Jeff would understand.

""Near the window was a large desk stacked with books and notebooks, and in the center of it sat a bulky, greenish-gray device that incorporated a video screen, a keyboard, and a printer. He frowned quizzically at it. What was she doing with a home computer so early? ... 'It's not a computer,' Pamela said. 'Wang 1200 word processor, one of the first. No disk drive, just cassettes, but still beats a typewriter. Want a beer?'""
 * Groundhog Day Loop: A particularly long one of 25 years. Notable that this book came out 8 years before Groundhog Day came out.
 * Groundhog Peggy Sue
 * Here We Go Again:
 * History Marches On: Several times.
 * In Spite of a Nail: Jeff tries to save JFK by getting Lee Harvey Oswald on the Secret Service's radar. JFK is assassinated anyway.
 * Its a Small World After All: Averted. There are relatively few replayers, and they only notice each other when one of them affects the timeline once - producing the movie Starsea.
 * The Jail Bait Wait: (Also see Legal Jailbait, below) The first time Jeff and Pam replay together, Pam is in her mid-teens.
 * Last Stand: For one replay, Jeff orders a staff of doctors and medical equipment to stand by to stop the heart attack that sends him back every October 18, 1988.
 * Legal Jailbait: Jeff replays to his early 20's while Pam is 14. This doesn't stop them from romance.
 * Make Wrong What Once Went Right:
 * Mental Time Travel
 * The Omniscient: Frank feels this way about Jeff after Jeff proves right over and over.
 * Point of View: Almost the entire book directly follows Jeff, save for a few times it switches to Pamela and the Epilogue.
 * Really Seven Hundred Years Old:
 * Serial Killer:
 * Set Right What Once Went Wrong: Jeff always ensures that Martin is wealthy enough to keep him from committing suicide.
 * Shown Their Work: Grimwood did a good job of researching the time period, from seeing which races and stocks would give the highest returns, to seeing when certain technology was available but hadn't taken off yet (ie, there were commercially available but expensive word processors and videotape machines available in the 1970's - long before both became popular in the 1980's )
 * The Slow Path
 * Tagline: If you could live your life over again...
 * Technology Marches On: With appearances of the Wang 1200 and Sony VTR. The following quote happens in 1974:


 * Take Our Word for It: The description of the tear-inducing movie Starsea, which in-universe was a blockbuster movie everyone was talking about, and the story Pamela tells her children of it.
 * Time Travel for Fun And Profit: And how. Jeff is lucky to start his first replay in May of 1963, right before two very high-stakes gambles - A [[http://en.wikipedia.org/wiki/Chateaugay_
 * Twenty Minutes Into the Future: Jeff's heart attack happens in 1988, but the book was published in 1986 - two years before 1988. The most up-to-date event covered is The Space Shuttle Challenger disaster, but the author remains purposefully vague on 1987 and 1988, because they hadn't actually happened yet. While there were arguably plenty of notable events in those years, luckily there was nothing on the level of another Pearl Harbor or a 9/11.
 * Unintentional Period Piece: Written in the 1980's, when people would find many of these events nostalgic. Now that it has been almost 25 years since it came out, it's more of a time capsule of the 25 year period.
 * What Year Is This
 * Who Shot JFK: Jeff tries to stop Lee Harvey Oswald a week beforehand, but realizes there must be a larger conspiracy because the assassination still happens, just with a different shooter.