I always enjoy home runs, but it really is something when a batter can hit the ball so hard that it reaches the upper deck. At both the old and new Yankee Stadiums, blasts to the upper deck in right field were fairly common. A high, majestic arc could reach some impressive places in that area, most notably from lefty hitters like Raul Ibanez and Barry Bonds, whose blast halfway up in the upper deck remains the hardest-hit ball I've ever seen at Yankee Stadium. Occasionally, a righthanded hitter could reach that area on an opposite-field homer, which I recall Derek Jeter and Alex Rodriguez doing at various times through the years.
Interestingly, the upper deck in left field was rarely explored. It was more difficult for righties to homer in Yankee Stadium than lefties, but down the line in left was only 318 feet. The left field upper deck was not that much further behind the bleachers than in right field. Yet it was a rare day when a righthanded belted one on a high enough arc to reach that deck. There are only a handful that I can recall watching or hearing about.
A-Rod reached that area a couple times. Once was on Old Timer's Day in 2004, and another occurred during his MVP season in '07. He also hit a ball there as a member of the Seattle Mariners back in the 2000 ALCS as well. Jose Canseco reportedly bombed one there in the late '80s, but aside from those four and another, I don't think I can remember any others. Jeter might have reached it once, but I am far from sure. Bernie Williams crushed some pitches from the right side of the plate that landed in the middle deck like his walk-off blast in the 1996 ALCS, but that is not quite upper deck.
The fifth homer that I know went to the left field upper deck is also the only that there has video on MLB.com. When switch-hitter Jorge Posada made contact with the ball, it could really rocket out of the park in a hurry. Take this roundtripper he hit off Bruce Chen and the Orioles on September 22, 2005:
Oof. Now that's a shot.
If there are any other left field upper deck dingers I missed, comment away.