...Rolex Super Coolness...
Bill Cosby is one of the biggest Rolex fans on earth and he has a huge collection of Rolex Day-Dates [a.k.a., The Rolex President]. Bill has been wearing Rolex watches for at least 45 years since he acted on the TV show, I Spy. Both Robert Culp and Bill Cosby both wore Pepsi GMTs on I Spy. If you want to learn much more about Bill Cosby and Rolex, you can on Jake's Rolex World.
On the Bill Cosby comedy album cover pictured above from 1965 named Why is there air? it shows Bill Cosby wearing his Rolex GMT 45 years ago. So this means he has been wearing Rolex for at least 45 years. This next shot is from I Spy, and shows Bill sporting his trademark Pepsi GMT Master.
In the next 2 photos below we see Bill Cosby during the Fat Albert & The Cosby Kids years, wearing a Yellow Gold Mocha GMT Master.