#2 - Michael Schumacher (5)
Michael Schumacher has more F1 wins than anybody else in the history of the sport, and five of his 91 came at Monaco. The first came in 1994 when he continued his perfect start to the season by crossing the line a full 37 seconds ahead of Martin Brundle.
It was a similar story in 1995, although he had to get past Damon Hill at the start for victory. Schumacher fell victim to the crazy conditions in 1996 by crashing out on the opening lap after qualifying on pole, but he got his first Monaco win for Ferrari the following season. The win in '97 was by a mammoth 57 seconds, when Schumacher won in Monaco, he often won by a big gap.
Schumacher's win in 1999 was his final before breaking his leg at Silverstone and ending his championship challenge, but 2001 contributed towards one of his typically dominant season displays, this being the fourth of nine victories that year.
Despite Schumacher's continued success through the early 2000s, he never won another race around Monaco, coming closest in 2004 before being taken out by Juan Pablo Montoya behind the Safety Car.