The Mrs. pointed me towards this thread, as I’ve been a comic fan since my early teens, and spent 5 years working in a comic store.
I absolutely agree with the comments both regarding Watchmen and Y the Last Man. I will go out on a limb and say outright that Watchmen-in my opinion-is one of the most over-rated graphic novels out there. Of course, Alan Moore has never really done anything I’ve enjoyed, except maaaaaybe V for Vendetta.
Y the Last Man, however, is one I always recommend. I think it’s a good “entry-level” type story, but it’s also clever and intelligent.
Would also recommend the following:
-Fables What if the characters of our childhood fables were real people, living in a secret part of New York? A wonderfully layered series.
-Locke and Key This is a newish series, so it might be the easiest to get into, if only for cost. Devilishly clever horror-type series.
-Queen and Country Female James Bond-type story by Greg Rucka
-Chew Funny little story about a cop who gets psychic impressions from the food he eats. Including suspects.
If you’re looking for single books/shorter series, I’d go with:
-Torso Based on the Cleveland Torso Murders of the 1930’s. Eliot Ness was the officer in charge of the investigation, coming on after the Al Capone case.
-The New Frontier I love Darwyn Cooke’s art (he’s also done Will Eisner’s The Spirit among other things) and the story is retro in its story line and art. Often interesting interpretations of some of the super heroes we think we know.
Sorry for the long list; this is just a topic close to my heart. If I can lure someone into comics, it’s fantastic. I’ve listed no super hero comics (apart from New Frontier). That’s not to say there aren’t great super hero books out there, but if you’re just getting into the medium, I prefer easing people into it through a different door. I think many people dispel comics as something for children and only associate them with super heroes. There’s another level to them entirely that I like to show people.