#2 Josh Hamilton - 2008
Arguably one of the most iconic Home Run Derby performances of all time, came from Josh Hamilton in 2008. It was the last year of the old Yankee Stadium and boy did Hambone send it out in style as he absolutely put on a show for the ages.
In the first round, Hamilton's seven competitors hit anywhere from three to eight homers. He hit eight himself, but also added twenty additional big flies, finishing the round with an astonishing 28 home runs. Highlighting the remarkable first round for Hamilton, was a stretch of 13 straight swings that resulted in homers. It was laughable how amazing the performance was.
Unfortunately, Hamilton ran out of gas after that opening round salvo. He hit four homers in the second round before stopping with only four outs to advance to the finals, where he would take on Justin Morneau of the Minnesota Twins. Morneau would best Hamilton in the finals, 5 to 3, but Josh was the story line and the guy everyone remembers from that night. Winning doesn't always mean finishing on top, and for Hamilton, he won the night despite taking second place.
#1 Juan Gonzalez - 1993
As with every year, the 1993 HR Derby field was stacked. Ken Griffey Jr., Barry Bonds, Cecil Fielder, Bobby Bonilla, Albert Belle, David Justice, and Mike Piazza were the competitors that 23-year-old Juan Gonzalez had to go toe to toe with at Camden Yards.
The youngster didn't blink and blasted seven bombs which tied Griffey Jr. for tops in the contest. The two athletes would then square off in a playoff. The playoff format had Griffey Jr. hitting first, and each player would get five outs. Junior started the overtime by hitting four bombs, but Gonzalez was not phased as he again matched The Kid with four of his own.
The two outfielders would then go to a double overtime, this time they were only allowed three outs. Gonzalez would hit first in this clash and was able to hit one out before recording his three outs. That one home run would prove to be just enough, as Griffey Jr. was unable to hit any over the fence. With the victory, Gonzalez became the youngest player to win the HR Derby. That record was challenged last season by Juan Soto who was also 23 years old when he won, but Gonzalez was one day younger than Soto and still holds the title of youngest HR Derby champion.