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Originally Posted by ZodWallop
I agree. His style of idealized libertarianism never really grabbed me. Tunnel in the Sky was one of his that I read. If you didn't like the beginning, I wouldn't expect it to get better.
My strongest memory is when the main character sees a fellow student die in front of him and his reaction is 'too bad!'
You have good taste 
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Hum, methinks we are heading towards drifting off topic, but I think that the main difference between the Clint Eastwood "Man with no Name" character and the John Wayne character in The Searcher and Stagecoach is more a matter of honor and ethics than anything else and The Outlaw Josie Wales was very, very close to the standard John Wayne character.
Early Heinlein is a product of it's time and rugged individualism was a common motif in both literature and film at the time. Yea, John Wayne was popular at the time, while Clint Eastwood's Spaghetti westerns were more a product of the 60's. If John Wayne compares to Heinlein, then Clint Eastwood compares to Roger Zelazny.
I wasn't a huge Tunnel in the Sky fan. I thought it was one of his weaker early works. The situation just seemed forced and unbelievable. I'm much more a Green Hills of Earth, Starship Troopers, The Moon is a Harsh Mistress fan.