Like many here, he's a sports car enthusiast, and one with ample resources (given his TV show was the most successful in US history). He has one of the largest Porsche collections, including the first and last 911's made, and a 959. That doesn't mean all that much to me, but perhaps explains his interest in chronographs.

He has an internet show that combines his interest in cars and comedy: "Comedians in Cars Getting Coffee". I've watched a couple episodes, can be amusing, but it may be an American thing.

http://comediansincarsgettingcoffee.com/

: Its a modern Navitimer . Watch is FAAAAR to big for his small
: wrist: looks lik a diving instrument and the clpas of this watch
: is awful looking too. Anyhow why is someone like him wearing
: such a watch at all. ?