George Clooney left the TV show ER in 1999
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George Clooney played the Dr. Douglas in the TV series "ER".
George left ER in 2009 to pursue a career in movies.
As a singer
Yes they are friends. George Clooney guest stared on Friends for 1 episode as a cute ER doctor. Friends and ER sets were near by each other. In addition, Clooney stared in Ocean's Eleven and Ocean's Twelve with Aniston's then husband Brad Pitt. Also Aniston participated in Clooney's telethon to help Haiti.
George Clooney married to Talia Balsam from 1989 to 1993 Yes, George Clooney married to Amal Alamuddin in September 27, 2014