"A Swift Pure Cry" is a disarming, very engaging first novel about a resourceful Irish teenager who steps in to take care of her younger siblings after the death of their mother. It is moving, witty, sharply observed and handily unsentimental. Because of the age of its central character, I suppose, the book has been marketed to "young adults." But like the best of these, it will speak clearly to any reader.

Under the 82nd Airborne is the book that made a Deborah Eisenberg fan of me. She is a very powerful AND engaging writer, and there is not a false word in her sentences. I would suggest starting with "Twilight of the Superheroes" because it is more current. At least two of the stories in it are nothing short of great. But she's pretty great altogether, so maybe you can't go too far wrong.

I think "The Stories of John Cheever" is (are?) a very good place to start. This is a very fat collection of stories written over many years. The situations and dilemmas of the characters are moving, and the writing is terrific in a completely straightforward way.

I was shocked, when I recently reread "The Scarlet Letter," to find that it begins with an introductory section called "The Custom-House." I had no memory of this; maybe it was excluded from the edition given to me as a ninth grader, or maybe it just meant nothing to me then. At all events, it is framing device for the story to follow and, at the same time, a fascinating piece of writing about work, government bureaucracies and especially writing. It gives you a wonderful, intimate sense of Hawthorne as a person. He is very witty, I was surprised to learn as a grownup.
All the same, I like "The House of the Seven Gables" better as a story, and would suggest starting there. It has great characters and a great plot (and the themes they make you write about in high school), and it is written with rich wit and terrific, close observation. Some of the characters feel entirely contemporary. I would say to start with that, but if you find you aren't liking it, try "The Scarlet Letter" before giving up on Hawthorne. Just make sure you get an edition with "The Custom-House" at the start.
I think it is a shame that high school students are given Hawthorne to read. They aren't old enough--haven't had a chance yet to live enough--to get him, and are consequently unlikely ever to try him again as adults.

Please do give Murdoch another chance. I like her very much but haven't read Jackson's Dilemma yet because I expect it to be a weak and atypical work. It was written very late in her career and there is some evidence that she had already started to develop Alzheimer's while writing it. I would suggest starting with The Black Prince or The Good Apprentice. If both are too dense for you, The Unicorn is a formally less complex novel but one I like very much.

"The Amazing Adventures of Kavalier and Clay" is one of the best books by a living author I have ever read--absorbing, entertaining, emotionally and historically resonant, and beautifully written. Definitely this is the place to start, unless you want to save the best for last.

I, too, would recommend starting with Lucky Jim--it is a memorably witty book. After years of cherishing Lucky Jim, though, I tried The Green Man not long ago. Very different book--for me, quite repellent. I also agree about the sexism, which I seem to recall was pretty evident in everything I've looked at of his. Didn't stop me loving Lucky Jim, though.

I would start with "Lord Jim" but switch immediately to "Nostromo" if you are not soon immersed and entranced. Both are amazing novels. "Typhoon" is a very different kind of book, a real adventure novel (not normally appealing to me) with quite a bit of humor as well as the more familar testing-a-man's-mettle theme. The central storm is described with a cinematic vividness that actually made me a little bit seasick. That doesn't sound like a pleasant experience, but it was great. I read "The Secret Sharer" only recently and found it intriguing but never resonant on the same level as the others I've mentioned.

I'd suggest starting with "Turbulent Souls," even though "Freakonomics" is the bestseller. The books are wholly different in form and purpose, of course, "Freaknomics" being co-written with a maverick economist and more in Dubner's journalist mode (though with his characteristic wit and acuity), while "Turbulent Souls" is a memoir. "Turbulent" tells an amazing story about Dubner's family: both parents born Jewish, both converted to Catholicism, and then Dubner's psychological journey to discover this history and trace out a circle back to Judaism. It is a fascinating and moving story--and also witty and acute.
"Confessions" is also a memoir and funny and honest and interesting as well--but for starters, definitely "Turbulent Souls."

"The Winshaw Legacy" is a very funny and winning book. Coe is a very clever writer. "The House of Sleep" is deeper and in some ways more memorable, but I would start with "Winshaw."

These are terrific stories--absorbing, honest, filled with recognizable people being squeezed by recognizable circumstances.

Here is a snippet from the book's review in the Boston Globe:
Profound and daring...some of the most wonderful stories any American has written...you emerge at the end as if from a display of heavenly fireworks - the mind ablaze with ideas, with fun, with pain, with admiration. Dazzling.

Another DebbiesIdea user asked in a comment if this book is typical of Murdoch's work. A very cogent review in the Boston Phoenix

http://www.bostonphoenix.com/alt1/archive/books/reviews/01-96/JACKSON_S_DILEMMA.html

sheds light on this question and suggests that the answer is no.