In my opinion, George Clooney should be emulating/mimicking Pitt's 20+ year career structure, and he's not. Clooney should be the ultimate classic / Golden Age leading man like Gregory Peck by now, but instead his filmography is totally dull. I've liked maybe three movies with him in it.
The Monuments Men
Gravity
The Descendants
The Ides of March
The American *
The Men Who Stare at Goats
Up in the Air
Burn After Reading
Leatherheads
Michael Clayton
Ocean's Thirteen
The Good German
Syriana
Good Night, and Good Luck.
Ocean's Twelve
Intolerable Cruelty
Spy Kids 3-D: Game Over
Confessions of a Dangerous Mind
Solaris
Ocean's Eleven
Spy Kids
The Perfect Storm
O Brother, Where Art Thou?
Three Kings
The Thin Red Line
Out of Sight
The Peacemaker
Batman & Robin
One Fine Day
From Dusk Till Dawn