George Clooney

Clooney rose to fame when he played Dr. Doug Ross on the hit NBC medical drama ER. Age: 32

In 1998, he co-starred in the crime-comedy Out of Sight opposite Jennifer Lopez, marking the first of his many collaborations with director Steven Soderbergh. Age: 36

In 2001, Clooney reunited with Soderbergh for the heist comedy Ocean's Eleven, a remake of the 1960s Rat Pack film of the same name, with Clooney playing Danny Ocean, originally portrayed by Frank Sinatra. The film cemented Clooney as a leading film star. Age: 39

In 2001, Clooney and Soderbergh co-founded Section Eight Productions. Age: 39

In 2005, Clooney starred in Syriana, which was based loosely on former Central Intelligence Agency agent Robert Baer's memoirs of his service in the Middle East. Clooney suffered an accident on the set of Syriana, which caused a brain injury with complications from a punctured dura. Age: 43

In September of 2006, he spoke to the UN Security Council with Nobel Prize-winner Elie Wiesel to ask the UN to find a solution to the conflict and to help the people of Darfur. Age: 44

The cover story in a February 2008 issue of Time magazine was headlined with: "George Clooney: The last movie star". Age: 46

In 2009, Clooney starred in the Jason Reitman directed comedy-drama Up in the Air. Age: 47

In 2011 Clooney starred in The Descendants as a husband whose wife has an accident that leaves her in a coma. Age: 49

On March 16, 2012, Clooney was arrested outside the Sudanese Embassy for civil disobedience. He intended to be arrested when he planned the protest. Age: 50

Clooney co-starred with Sandra Bullock in Gravity (2013), a space thriller directed by Alfonso Cuarón. Age: 51

In 2013, Clooney co-founded Casamigos Tequila with Rande Gerber and Michael Meldman. It was sold to Diageo for $700 million in June 2017, with an additional $300 million possible depending on the company's performance over the next ten years. Age: 51

On January 11, 2015, Clooney was awarded the Golden Globe Cecil B. DeMille Lifetime Achievement Award. Age: 53

In 2019, Clooney returned to television, starring, directing, and producing the Hulu historical miniseries Catch-22 based upon the novel of the same name by Joseph Heller. Clooney was initially cast in a main role in the series; however, he opted to take a smaller supporting role instead. The series premiered on May 31, 2019, to critical acclaim. Age: 57

In 2023, Clooney reprised the role of Bruce Wayne / Batman in a cameo in The Flash. Age: 61