Rise to Fame
He spent thirteen pilots and most of his thirties playing characters nobody remembers before ER put him on the map at 33. The 1995 episode where Dr. Doug Ross pulled a boy from a flooded drain got him cast as Batman the next day. That felt like the peak until Batman & Robin came out and nearly ended everything. Soderbergh's Out of Sight rebuilt the credibility, and a Best Supporting Actor Oscar for Syriana in 2006 finished the comeback.
In the Spotlight
Casamigos, the tequila he co-founded in 2013, sold to Diageo for $700 million in 2017 and reportedly netted him around $230 million before taxes. That single deal outpaced his entire acting career. Since then he's been running two lanes at once: Jay Kelly earned a Golden Globe nomination in 2026, and his Broadway Good Night, and Good Luck broke records and landed five Tony nominations. Getting French citizenship while publicly feuding with Trump is apparently his idea of a quiet year.
Side Notes
He grew up in Augusta, Kentucky, cutting tobacco for $3 an hour on his grandparents' farm. The Cincinnati Reds cut him in 1977 after the first round of tryouts, which redirected the whole trajectory. When he moved to L.A., he slept on a mattress in a closet and shared space with a potbellied pig named Max, who woke him before the 1994 Northridge earthquake.