[[quoteright:200:http://static.tvtropes.org/pmwiki/pub/images/200px-Replay4166ZHz9Sb_398.jpg]]
[[caption-width-right:200:Original cover]]

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 GroundhogDayLoop. 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:

* AlternateHistory: Given the length of time this character loops, each "replay" is one of these by differing degrees.
* AuthorExistenceFailure: Ken Grimwood was writing a sequel when he died in 2003.
* CloudCuckooLander: One of a darker variety.
* CynicismCatalyst: [[spoiler: Jeff's daughter from his first replay, who he can never get back.]]
* DrivenToSuicide: Jeff's college roommate, Martin, committed suicide in the original timeline.
* DoWellButNotPerfect: 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}}: [[spoiler: A different shooter kills JFK after Jeff's intervention, setting up the quasi-government agency that hold Jeff and Pamela prisoner a few replays later, trying to extract information from them.]]
* FreeLoveFuture: Jeff's girlfriend in 1963 wants to help him get off but remain a TechnicalVirgin. 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 [[TheHedonist he has a lot of sex and experiments with drugs]] he muses to himself that the future of the 1980's has AIDS.
* EveryoneIsJesusInPurgatory: Invoked in-universe in an art exhibit Pamela made for public viewing but knew only Jeff would understand.
-->"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."
* GroundhogDayLoop: A particularly long one of 25 years. Notable that this book came out 8 years before ''Film/GroundhogDay'' came out.
* GroundhogPeggySue
* HereWeGoAgain: [[spoiler: A different, completely unrelated character in the epilogue wakes up in 1988, having just had a heart attack in 2017.]]
* HistoryMarchesOn: Several times.
* InSpiteOfANail: Jeff tries to save JFK by getting Lee Harvey Oswald on the Secret Service's radar. JFK is assassinated anyway.
* ItsASmallWorldAfterAll: Averted. There are relatively few replayers, and they only notice each other when one of them affects the timeline once - producing the movie ''Starsea''.
* TheJailBaitWait: (Also see Legal Jailbait, below) The first time Jeff and Pam replay together, Pam is in her mid-teens. [[spoiler: Pam skews late, and Jeff causes some uncomfortable moments with Pam's family before Pam arrives for her replay. Once she replays they spend time together on their "dates to the movies", by going to a hotel instead since they both can recite the plot of any movie playing from memory.]]
* LastStand: 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. [[spoiler: The doctors are confused that an otherwise healthy man is so worried - but the heart attack hits all the same and despite the doctor's efforts he's sent back again.]]
* LegalJailbait: Jeff replays to his early 20's while Pam is 14. This doesn't stop them from romance.
* MakeWrongWhatOnceWentRight: [[spoiler: One replay Jeff and Pamela think they are improving things by going public. They don't, big time.]]
* MentalTimeTravel
* TheOmniscient: Frank feels this way about Jeff after Jeff proves right over and over. [[spoiler: It gets to be a little too much for him when he discovers Jeff was in Dallas a week before JFK is shot, so he cuts off ties with Jeff.]]
* PointOfView: Almost the entire book directly follows Jeff, save for a few times it switches to Pamela and the Epilogue.
* ReallySevenHundredYearsOld: [[spoiler: By the end of the book, Jeff is 202 years old in a 43 year old body.]]
* SerialKiller: [[spoiler: One replayer is certainly making the most of his repeats.]]
* SetRightWhatOnceWentWrong: Jeff always ensures that Martin is wealthy enough to keep him from committing suicide. [[spoiler: Also the replay where he has a healthy relationship with Linda.]]
* ShownTheirWork: 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 )
* TheSlowPath
* TagLine: ''If you could live your life over again...''
* TechnologyMarchesOn: With appearances of the [[http://www.wang1200.org/ Wang 1200]] and [[http://en.wikipedia.org/wiki/1%22_type_C_videotape Sony VTR]]. The following quote happens in 1974:
-->"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?'"
* TakeOurWordForIt: 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.
* TakeThat: A mild one, where Jeff first meets Pamela and asks her about her filmmaking plans after ''Starsea''. At one point he suggests that if she produces ''Film/RaidersOfTheLostArk'', she should "talk to [[Creator/StevenSpielberg Spielberg]] about [[Film/IndianaJonesAndTheTempleOfDoom the first sequel]]".
* TimeTravelForFunAndProfit: 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_%28horse%29 not-expected to win Kentucky Derby Horse]], and the [[http://en.wikipedia.org/wiki/1963_World_Series Dodgers sweeping the Yankees in the World Series]]. [[spoiler: That is, until his replays start happening after those events happen.]]
** Pamela does this as well; during one replay she creates a hugely successful film called ''Starsea'', recruiting two unknowns to helm the project--director Creator/StevenSpielberg and special effects producer GeorgeLucas.
* TwentyMinutesIntoTheFuture: 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 [[http://en.wikipedia.org/wiki/Challenger_disaster 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 [[WorldWarII Pearl Harbor]] or a 9/11.
* UnintentionalPeriodPiece: 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.
* WhatYearIsThis
* WhoShotJFK: 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.