Weah, 51, remains the only African in history to win the most coveted individual honour in world football, the Ballon d'Or, after a scintillating title-winning season with AC Milan in the 1995/96 season.
The now Liberian president scored 193 goals in 478 games, representing AC Monaco, Paris Saint-Germain, Milan, Chelsea, Manchester City and Marseille over 15 seasons in Europe and was known for his incredible technical ability and searing pace.
Drogba burst onto the European scene while in the colours of Marseille, but it was at Chelsea where the Ivorian beast earned himself legendary status and struck fear into defenders in the English top-flight.
The 39-year-old had two spells with the Blues and helped the London-based side win 12 major titles, won the Premier League Golden Boot twice and scored 164 goals in nine seasons. He will forever be remembered for scoring the penalty that won Chelsea its one and only UEFA Champions League title.
The new generation
Last month Drogba's son Isaac joined one of his father's former sides Guingamp, signing his first professional contract at the age of 17 but can he make the similar impact?
Timothy Weah, on the other hand, has already earned rave reviews at his current club Paris Saint-Germain, where the 18-year-old made his first-team debut for the league leaders on Saturday during the 2-0 win over Troyes.
His performances within the academy and four goals in 11 UEFA Youth League fixtures convinced head coach Unai Emery to draft the teenager into the first-team squad but unlike his father, Timothy is set to represent the United States national team.
While it may be a loss to African football, the son of the 1996 Ballon d'Or winner was born in the USA and had the choice of representing the country of his fathers birth, France or Jamaica due to his mother's heritage.
With both teenagers being strikers with an ingrained background of success, they hold all the tools at their disposal to go on and emulate the successful careers of their fathers that shared five African Footballer of the Year titles between them.
But the question remains; could we be witnessing the beginning of a fierce rivalry between two of Africa's biggest names within a new dawn of European football?