#5 - Sir Stirling Moss (3)
Like his fellow Brit, Sir Stirling Moss had a real knack around Monaco. The Circuit de Monaco was very different in the 1950s, but the same skill set was required to be faster than the competition. Moss had competed in Formula 1 since 1951, but only became a full-time driver in 1955, a year before he took his first winner's trophy in Monaco.
Moss' three wins may not seem too impressive compared to some of the other names on this list, but he competed in 7 and finished in just four, thanks to the poor reliability of the era. These were also the days when the Monaco Grand Prix was a gruelling 100 laps and took almost three hours to complete.
Sir Stirling also won with three different constructors - Maserati, Rob Walker and Lotus - which is still a record and includes back to back wins in 1960 and '61. Had Moss not had the accident which caused him to retire at the end of 1961, he could've easily won a world championship and perhaps extended his record of Monaco wins.