Frank Kelly Freas
1955, 1956, 1958, and 1959 Hugo Winner for Best Illustrator
In case you're wondering what happened to 1957, that year awards were only given to magazines.
I should mention that the covers that I've been using have mostly been from sfcovers.net where they have a very nice collection of magazine covers. I recommend taking a look, especially at Freas's early work. While I've been trying to pick out a favorite image from the period that he won and balance it with the other selections his work in 1954 (for which he won the 1955 Hugo) is simply impressive. I chose the one on the right because it illustrates the Hugo winning They'd Rather Be Right, but I enjoyed the July 1954 cover of Planet UK. It is a nice illustration and rather comically refers to just the title of Bradbury's "The Sound of Thunder" which has nothing to do with the illustration that was used (something that many science fiction writers over the years would complain about).
Also of note, the 1956 image is an illustration for Double Star while the last one features Clifford Simak's "The Big Front Yard". The remaining image was chosen because much like the editors of the science fiction magazines of the 1950's I know that to get some readers you have to use some cheesecake.
"Or All the Seas with Oysters"
by Avram Davidson
1958 Hugo Winner for Best Short Story
"Or All the Seas with Oysters" is a first for the Hugo awards. This is the first fiction that is not science fiction to win. It's possible that there is a science fiction explanation for the events in the story but I'd categorize the work as one of fantasy. Along with the next year's "The Hell-Bound Train" this story made it clear that the Hugo would not be limited to the strict form of science fiction. While some people looking at the recent Hugo winners may not be happy with that I think it was a good decision on the part of that year's voters.
This story is also a good decision on the part of that year's voters. It isn't a very deep story and its big idea has been done quite a few times since it was written but this version is in turns charming and sinister and I enjoyed it.
There isn't a lot of narrative to "Or All the Seas with Oysters". Two bicycle repairmen notice that safety pins always vanish and reappear while you end up with a closet full of unused clothes hangers. One of them begins to ascribe a possible life cycle to these bits of found metal and sees something sinister behind it.
The story is very light-hearted but given the direction things take I could have easily seen this tale being done by H.P. Lovecraft (it's just a matter of time until there are enough clothes hangers to supplant humanity; they are smaller but they breed faster and how many times do you let one of them get close to you without thinking about it). It has that same kind of creeping dread as it shifts tone. It elevates what could have been a simple comedic piece to something more and I have to recommend it.
"The Hell-Bound Train"
by Robert Bloch
1959 Hugo Winner for Best Short Story
It's been said that the most common fantasy story is the deal with the devil. It's a common trope for writers who don't typically do any kind of fantasy to fall back to. Bloch in "The Hell-Bound Train" was not acting as one of those people. In 1959 he was a science fiction and fantasy writer with a taste for horror. He was co-presenter at Worldcon that year. And then he must have made his own deal with the devil because less than one year later came the film Psycho and he was noticed by the mainstream public.
I'd like to say that "The Hell-Bound Train" is not a typical deal with the devil story. The devil in it is wittier and more clever than most. He isn't relying on trickery or clever wording to bring him the soul, just human nature. He makes references to other stories that feature this same plot and lets the reader know that the methods of cheating him used then wouldn't work this time. Unfortunately I feel that the rest of the story lacks the same strength as the characterization of Old Scratch.
Admittedly fifty years on this kind of thing has been done quite a bit more but Bloch's story still has a charm there. The problem for me is the very ending where it falls back into the standard pattern of these stories. After doing so well with the set up the ending is a flat disappointment for me. Given the overdone nature of the story and that disappointing ending I'd have to just forget about this one.
"The Big Front Yard"
by Clifford D. Simak
1959 Hugo Winner for Best Novelette
"The Big Front Yard" reminds me a lot of Simak's Waystation. It's a simple, pastoral story wonderfully told. The concepts aren't wildly mind blowing, the biggest action in the book is a lost dog, and I can't say that I completely agree with the climax which is dependent upon aliens who can bend space wanting to open technological trade with earth but Simak brings in a bucket of charm to make it all work.
In "The Big Front Yard" Hiram is a tinkerer and antique salesman who finds that his house has been turned into a gateway to another planet (rather like Waystation there). As he explorers this new world and finds similar houses that act as gates his dog wanders off but everything is made better as it wanders back with aliens who want to trade with Hiram.
Obviously that's simplified but not by much. Simak's story is more about the life of a Yankee trader, a concept that's pretty much gone now, than it is about the strange alien planet. It's populated by easy-going characters; even the money-grubbing businessman who tries to take advantage of Hiram is laid back.
I think the worst thing I can say about "The Big Front Yard" is that it is redundant. After reading Waystation I felt like I've already read a better version of this same story. Still I can't complain that much about "The Big Front Yard", it was a pleasant experience.