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The Grateful Dead (偉大なる死 Idainaru Shi)
Bruno Bucciarati vs. Prosciutto

Following instructions written on the key, Team Bucciarati boards a train headed to Florence, aiming to reach Venice. Having been instructed to pick up a turtle at the station's drinking fountain, Bucciarati notices a hole in the turtle's shell in the shape of the key. He inserts the key into the hole... and he and the others are sucked inside! Turns out this activated the turtle's Stand, Mr. President, creating a secret room inside the key for the team to hide out in. Meanwhile, two assassin brothers, Prosciutto and Pesci, have also boarded the train. In a ploy to lure the heroes out, Prosciutto activates his Stand, The Grateful Dead, as the two begin to search the train. Inside the turtle, Mista asks a seemingly unwell Narancia if he's alright... and Narancia asks if he said something, having suddenly aged into a senior! Immediately deducing it to be a Stand attack, Bucciarati muses that this may be trying to draw them into a trap, before sending Mista to investigate. Entering another car, Mista sees that every other passenger has rapidly aged, as well. As he wonders if they're dead and remarks on the enemy's lack of restraint, one elderly passenger calls out to him and grabs his wrist... before launching a surprise attack and turning Mista into a senior, too! As Mista falls unconscious, Pesci runs in and praises his brother, the now-normal-age Prosciutto standing and picking up Mista's revolver before firing three shots into his head. The brothers then leave for the car Mista came from... and the bullets in Mista's head are pushed out; looks like his Stand, Sex Pistols, saved his life. Looking around the car, the two assassins discover the turtle, and see the heroes inside. However, they realize that one person is missing... Bucciarati, who promptly emerges from a zipper in the ceiling, knocking out Pesci with a surprise attack before facing Prosciutto.

You now control Bucciarati, with your goal being Prosciutto's defeat. The Grateful Dead's aging power will slowly drain your health over time, and Prosciutto can use a grab attack to briefly accelerate the health drain. This fight is one where the Secret Factors can really help out, as the second can negate the health drain, and the third and fourth will help end the fight quickly.

Secret Factors
The first Secret Factor must be achieved before the second. The third Secret Factor becomes possible when the second is activated, and the fourth is possible when the third is activated.
1. Shoot Pesci. (ペッシをシュート)
Stand Shoot the knocked-out Pesci at the north end of the cab. This rewards you with +2.
2. Attack the ice dispenser to obtain ice. (氷サーバーを壊して氷を取り出す)
Attack the drink dispenser at the south end of the cab. This will activate a cutscene where the machine's ice falls out, and Bucciarati picks it up, realizing that Prosciutto is aging people through their body temperature, and concludes that ice can prevent the aging effects of The Grateful Dead. In addition to disabling the health drain for around thirty seconds each time the machine dispenses ice, this rewards you with +2.
3. Shoot the wall to create a zipper hole. (壁をシュートして壁にジッパー穴をあける)
After the second Secret Factor is achieved, Stand Shoot the wall at the northwest corner of the cab. This will open a zipper in the wall, and activates a cutscene where Prosciutto notices the zipper behind him and realizes that Bucciarati plans to throw him out of the train. This rewards you with +3.
4. Throw Prosciutto out of the train through the zipper. (ジッパー穴でプロシュートを車外に落とす)
After the third Secret Factor is achieved, knock Prosciutto through the zipper on the wall. Not only will this reward you with +3, but this also ends the fight instantly.