So having collected all of the films and television shows that have won I have to say it's an impressive list:
1958 - The Incredible Shrinking Man
1960 - The Twilight Zone
1961 - The Twilight Zone
1962 - The Twilight Zone
1965 - Dr. Strangelove
1967 - Star Trek: "The Menagerie"
1968 - Star Trek: "City on the Edge of Forever"
1969 - 2001: A Space Odyssey
1970 - News coverage of Apollo XI
1972 - A Clockwork Orange
1973 - Slaughterhouse-Five
1974 - Sleeper
1975 - Young Frankenstein
1976 - A Boy and His Dog
1978 - Star Wars
1979 - Superman
1980 - Alien
1981 - The Empire Strikes Back
1982 - Raiders of the Lost Ark
1983 - Blade Runner
1984 - Return of the Jedi
1985 - 2010
1986 - Back to the Future
1987 - Aliens
1988 - The Princess Bride
1989 - Who Framed Roger Rabbit
1990 - Indiana Jones and the Last Crusade
1991 - Edward Scissorhands
1992 - Terminator 2
1993 - Star Trek: The Next Generation: "The Inner Light"
1994 - Jurassic Park
1995 - Star Trek: The Next Generation: "All Good Things"
1996 - Babylon 5: "The Coming of Shadows"
1997 - Babylon 5: "Severed Dreams"
1998 - Contact
1999 - The Truman Show
2000 - Galaxy Quest
2001 - Crouching Tiger, Hidden Dragon
2002 - The Lord of the Rings: The Fellowship of the Ring
2003 - The Lord of the Rings: The Two Towers and Buffy the Vampire Slayer: "Conversations with Dead People"
2004 - The Lord of the Rings: The Return of the King and Gollum's Acceptance Speech at the 2003 MTV Movie Awards
2005 - The Incredibles and Battlestar Galactica: "33"
2006 - Serenity and Doctor Who: "The Empty Child" and "The Doctor Dances"
2007 - Pan's Labyrinth and Doctor Who: "Girl in the Fireplace"
2008 - Stardust and Doctor Who: "Blink"
For the most part they're safe choices but that isn't a bad thing since most of the movies are reasonably good. I might not think they're the best film of that year for the most part but I don't hate them.
There's really only six awards on the list where I think a bad decision was made and most of them took the Hugo because of their connection to something better that was beloved by fandom. The six I don't care for are:
- Slaughterhouse-Five (from a much superior Vonnegut book)
- A Boy and His Dog (from a better Harlan Ellison novella)
- 2010 (sequel to 2001)
- Contact (from the Carl Sagan novel and released shortly after his death)
- Buffy the Vampire Slayer: "Conversations with Dead People" (the introduction of the short form dramatic presentation Hugo opened the door to television again but years after the show actually deserved to win)
- Gollum's Acceptance Speech at the 2003 MTV Movie Awards