I am a Marvel boy at heart, but like most of us I also cross into the other universe a lot as well. Howeverm it is really only for Batman and Green Arrow, or the big storylines. I always want to expand and to me that means trying to get into Superman. However, I just don't like Superman. But I want to like him. He is boring to me. But I don't want him to be boring. I bring this up in part because of how much I don't care about Man of Steel coming out and also as I just kinda seen in my comic collecting how I really lack anything Superman. I love Smallville and I loved Superman Secret Origin by Johns. Outside of that he never appeals to me. He was never that cool to me in the Crisis storylines. I only like Siperman/Batman stories because of Batman. I hated All Star Superman, with a passion. I was confused pre-New 52. I hated Morrison's attempts on Action Comics post-New 52. I turn to you peeps to help me like him. I recognize how much he means to the medium and I want to open my eyes to the world of Superman.
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90's, sure, but he went out like a beast.
Yes, I know, I probably didn't help. Sorry.
I recommend picking up any of the collections that compile the stories from post-Crisis up to just short of Superman 2YK, basically the so-called Byrne Superman from 1985 - 2000. That was the best and most readable period for Superman.
The best is "Whatever Happened to the Man of Tomorrow?". I read this very nostalgic Silver Age-y story while caught up in the early '90s shock-value/Image/grim'n'gritty boom, and I still loved it. I loved it even though I had almost no idea about the history it was referencing because... I didn't need to. The greatness of the character comes through here very strongly.
Other than that... it was things like Moore's runs on "Supreme" and "Miracleman", both of which are sorta Supes analogs at times, which made me love the character and also feel very, very annoyed that very few of the bajillion Superman issues produced since then captured much of the same spirit.
As far as more recent comics go, I liked what I read of Johns' "Action" run. You can probably find many issues of that in dollar bins. And I liked the odd Busiek/Pacheco "Superman" issue.
I can't really strongly recommend anything else for a sort of entry-level "make me like this character" story. I've never read "Man for All Seasons" but I would assume it's good.
For the record, I liked Morrison's "All Star", but not nearly as much as most other people seem to. Many have said that this is one of the few Morrison books that they can unabashedly love, but to me it just seemed to rely too much on surface-level nostalgia at times. Still a good series overall, I guess. I detested his "Action" run while it was coming out, but I recently reread the whole thing and it holds up and fits together MUCH better than I thought it would. All in all, I don't think Morrison is suited to Superman anywhere near as well as he WANTS to be or TRIES (so damn hard) to be.
But, yeah, I would try to find "Whatever Happened to the Man of Tomorrow?". It is billed as the "last" Superman story, but for me it was the first Superman story that made an impression on me.
There's also Superman/Batman: Generations by John Byrne, which is an Elseworlds series about the Superman & Batman team that spans the years and (as the title suggests) the family lines into the future. A good, fun read.
Since no one else listed it I may be in the minority though
After that is the superman cartoon episode where he races flash
Good luck maybe the new movie will be the new benchmark
http://en.wikipedia.org/wiki/Brainiac_(story_arc)#Collected_editions
Superman: Red Son
Superman for all Seasons
Superman: The Man of Steel
Superman: For the Man Who Has Everything, by Moore (the animated JLI episode is also top notch)
Alan Moore's Supreme
Alex Ross and Paul Dini's Superman Peace on Earth
Kingdom Come
Justice
Superman Secret Identity
Superman Adventures
Superman the Animated Series ( if you can watch his beat-down with Darkseid, and not come out a Superman fan, you have no soul.)
It's interesting: I find myself seeing more depth to the character through certain people's eyes... Alan Moore and Alex Ross, for example.
Superman is a wonderful character, and badly written 95% of the time. But those diamonds in the rough, are really spectacular and show the character's potential as a storytelling device.
Matthew
I'd say try different things that sound interesting to you, not what's recommended. People tried to tell me to stick with Morrison's Batman run. Truth is, despite how interesting his stories might be, I just didn't care for his take on the character.
I am by far not a Superman fan, in almost 3 decades of collecting, I probably had 2 dozen issues of his titles. He's just a character that doesn't appeal to me.
Having said that, I think Man of Steel is going to be a version I'm very interested in. I want to see a version where he feels like an outcast. Where he's trying to connect with people & find his place. Make viewers question if they would really want to be Superman.
One of the things that always bothered me about the first Superman movie was how quickly everyone trusted & accepted him.
M
Superman for All Seasons
Superman: Secret Identity
Superman: Red Son
Speeding Bullets
Last Son
Whatever Happened to the Man of Tomorrow?
Superman: The Man Of Steel series of trades
Superman: Brainiac
Superman: Birthright
Superman: For the Man Who Has Everything