Reddit reviews Superman: Time and Time Again

Red Son is fantastic, but if you are not too familiar with Superman then you may not appreciate it as much. All Star is great too as a standalone, alternate story.

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But it all depends on what kind of stories you like. If you like origin stories, then get Byrne's Man of Steel, Waid's Birthright, Johns's Secret Origins and Loeb's For All Seasons.

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If you are familiar with Superman in general, then you may want to get into the alternate versions like Red Son, Earth One, Secret Identity, Last Son of Earth (an interesting twist on Last Son of Krypton), The Nail, Superman - Batman Generations (I think there were 2 or 3 series of this), Kingdom Come.

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If you want stories contained in continuity then Time And Time Again, Superman: Exile, Death of Superman, Reign of the Supermen, Return of Superman. These are all great reads

It's from this collection:

http://www.amazon.com/Superman-Time-Again-Dan-Jurgens/dp/1563891298

Great little series. Immediately after Lois and Clark are engaged Superman gets caught in a temporal explosion and ends up getting bounced all over time, the future and past. It's a really great little collection.

(it's post COIE, Pre-infinite Crisis, new 52 era)