Oliver Reed and the Sailors
Oliver Reed has a lengthy history in film, having played legendary roles such as Bill Sikes in Oliver! back in 1968, and it's even been reported that he was in the running to replace Sean Connery as James Bond back then. Modern audiences would most likely recognize him from his final appearance as gladiator trainer Proximo in the film Gladiator. Reed died while filming Gladiator, and, like many of the characters he played, he went out with a bang. Reed was an alcoholic in real life, which was well recognized and even applauded. He enjoyed drinking and didn't try to disguise it.
During a break in Gladiator filming, Reed decided to decompress in the only way he knew how: by going way too far. He engaged in a drinking contest with some sailors, consuming 8 pints of beer, 12 shots of rum, cognac, and a half bottle of whisky. He was 61 years old at the time. He also chose to arm wrestle five of the sailors as part of his intoxicated feats of strength. He defeated them all, but then had a massive heart attack. He passed away on the way to the hospital.
Date: 1999