I'm not going to take into consideration the identities of the participants, or the identities of the broadcasters. I think we all know that every Home Run Derby announced by Chris Berman is the worst Home Run Derby of all time.
Rather, I'm just going off of results, here. The Home Run Derby has been in existence as a competition in something like its present form since 1985. Which of them have been the least entertaining from a fan's perspective?
The format for the Home Run Derby used to be a little different than it is now. Rather than three rounds with ten outs each, the derby was once a lot shorter. It was structured as a two-inning affair, where each participant would be given five outs per inning. One would expect, then, given this and several other reasons, that Home Run Derbies through 1990 would feature considerably lower homer totals than their more contemporary counterparts.
Still, the leader in 1985 - Dave Parker - blasted six home runs. 1986 featured a tie between Wally Joyner and Darryl Strawberry, who each hit four.
1987 featured eight home runs. Total.
Granted, a big part of this is that the 1987 Home Run Derby only had four participants. 1985 had ten. 1986 had six. With fewer hitters, you expect fewer homers. Even so, Andre Dawson led everyone with four, Ozzie Virgil Jr. had two, and George Bell and Mark McGwire settled for one apiece.
Eight home runs in a home run derby. In September that same year, the Toronto Blue Jays hit ten home runs in eight innings against actual, Major League pitchers who were trying to get them out.
The 1987 Home Run Derby only featured eight home runs, but then, there were only four participants. At least it made some degree of sense.
The 1990 Home Run Derby featured eight participants. These eight participants combined to hit 291 home runs during the regular season.
They combined to hit five home runs in a competition explicitly designed so as to maximize home runs.
I don't know exactly what happened. The competition took place in Chicago's Wrigley Field, so it's possible Wrigley was having one of its Wrigley days, where the wind was blowing in straight on the hitter's face or something. But whatever the case, this derby averaged fewer than one home run per participant. In 2008, Josh Hamilton hit 13 consecutive dingers on his own without making a single out.
1990 was a bummer of a derby, as Ken Griffey Jr., Bobby Bonilla, Darryl Strawberry, Cecil Fielder, and Jose Canseco could've matched their dinger output by falling gravely ill and checking into the hospital.
1988 -- Riverfront Stadium, Cincinnati -- Canceled due to rain